Organic Chemistry Practice Test

7/23/2019 Organic Chemistry Practice Test

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Organic Chemistry, 5e(Bruice)

Chapter 1: Electronic Structure and Bonding Acids and Bases

1)

Atoms with the same number of protons but different numbers of neutrons are called __________.Answer:

isotopesType: SASection: 1-1

2)

Which of the followin elements does this electronic confiuration represent!

1s22s22p"

A)

#$)

%%)

&')

Al()

Answer:

AType: *%Section: 1-2

+)

,ow many unpaired electrons are present in the isolated carbon atom atomic number /)!A)

none

$)

one


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%)

two')

three

()

four

Answer:

%Type: *%

Section: 1-2

0)

Which of the followin is the electronic confiuration of the element #e!

A)

1s22s22p/+s2+p/0s2+d/

$)

1s22s22p/+s2+p+d/

%)

1s22s22p+s2+p/0s2+d/

')

1s22s22p/+s2+p/0s20d/

()

1s22s22p/+s2+p/0s20p/

Answer:

AType: *%

Section: 1-2

")

The atomic number of boron is ". The correct electronic confiuration of boron is:A)

1s22s+

$)


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1s22p+

%)

1s22s22p1

')

2s22p+

()

1s22s2+s1

Answer:

%Type: *%

Section: 1-2


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/)

Which of the followin statements correctly describes the third electron shell that surrounds the nucleus of an atom!

A)

The third shell contains onlysandpatomic orbitals.

$)

The maimum number of electrons that can occupy the third shell is 1.

%)

The total number of atomic orbitals present in the third shell is 1/.

')

The third shell can containforbitals.

()

All third shell elements must ha3e d electrons.

Answer:

$Type: *%

Section: 1-2

4)

Ar5 675 %l-are isoelectronic elements elements with the same number of electrons). What orbital does the last

electron occupy!

Answer:

+p orbitalType: SA

Section: 1-2

)

The compound methylamine5 %,+&,25 contains a %-& bond. 8n this bond5 which of the followin best describes

the chare on the nitroen atom!

A)

71

$)

slihtly positi3e

%)

unchared


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')

slihtly neati3e()

-1

Answer:

'Type: *%

Section: 1-+

9)

Which of the compounds below bond predominantly 3ia ionic bondin!

A)

6%l

$)

%#0

%)

&,+

')

both A and $

()

both $ and %

Answer:

AType: *%

Section: 1-+

1)

What type of bondin is most important in %,+%,2%,2%,2%,2%,+!

A)

ionic$)

hydroen%)


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co3alent

')

polar

Answer:

%Type: *%

Section: 1-+

11)

Which of the followin contains) polar co3alent bonds!A)

&,+$)

&a2

%)

,2

')

6#

()

both A and %Answer:

AType: *%Section: 1-+

12)

Which of the followin co3alent bonds has the larest dipole moment!

A)

%-%

$)

%-,

%)

%-


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')

,-&()

,-#

Answer:

(Type: *%

Section: 1-+

1+)

;sin the symbol


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A)

72

$)

71

%)

')

-1

()

-2

Answer:

$Type: *%Section: 1-0


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14)

Which of the followin is the most liely electronic structure for %2,2!

A)

$)

%)

')

,%%,

()

Answer:

'Type: *%Section: 1-0

1)

Which of the followin structures5 includin formal chares5 is correct for diaBomethane5 %,2&2!

A)

:%,2&&:$)

%)


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')

()

Answer:

'

Type: *%Section: 1-0


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19)

What are the formal chares on nitroen and the starred oyen atom in the followin molecule!

A)

& -15

$)

& 715 -1

%)

& 715 71

')

& -15 -1

()

& 715 Answer:

(Type: *%Section: 1-0

2)

'raw the 6eulC structure for each of the followin:

a. %,+%,2, b. %,+%, c. %,+)+%7

Answer:


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Type: SA

Section: 1-0

21)

The 6eulC structure of pentane is shown below. 'raw the condensed structural formula which corresponds to this

Dewis structure.

Answer:

%,+%,2)+%,+Type: SA

Section: 1-0


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22)

'raw condensed structures for the four compounds with formula %+,9&.

Answer:

%,+%,2%,2&,2%,+%,2&,%,+

%,+)2%,&,2

%,+)+&

Type: SASection: 1-0

2+)

Write a Dewis structure for the molecule i3en and show all formal chares.

%,2%

Answer:

Type: SA

Section: 1-0

20)

(pand the condensed structure below to show the co3alent bonds and the lone-pair electrons.

%,+)2%,%,2%,

Answer:


2")

'raw the Dewis structure for %,+&27.

Answer:


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2/)

,ow many distinct and deenerate p orbitals eist in the second electron shell5 where n 2!A)

$)

1%)

2')

+()

0

Answer:

'

Type: *%Section: 1-"


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24)

'raw the shape of a 2p orbital.

Answer:

Type: SASection: 1-"

2)

%onsider the interaction of two hydroen 1s atomic orbitals of the same phase. Which of the statements below is anincorrect description of this interaction!

A)

A sima bondin molecular orbital is formed.

$)

The molecular orbital formed is lower in enery than a hydroen 1s atomic orbital.

%)

The molecular orbital formed has a node between the atoms.

')

The molecular orbital formed is cylindrically symmetric.

()

A maimum of two electrons may occupy the molecular orbital formed.Answer:

%Type: *%

Section: 1-/

29)

$oth sima E) and pi F) bonds can be formed by o3erlappin p orbitals. 'escribe the difference.

Answer:

Sima bonds are formed from the o3erlap of atomic orbitals alon a circular ais of symmetrical nature5 i.e.5 head-

on o3erlap. All sinle bonds are sima bonds.

=i bonds are formed from the o3erlap of atomic orbitals alon a non-symmetrical parallel) ais5 i.e.5 side-to-side

o3erlap. 'ouble and triple bonds contain both sima and pi bonds.


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Type: SASection: 1-/

+)

What ind of molecular orbital E5 EG5 F5 or FG) results when the two atomic orbitals shown below interact in the

manner indicated!

Answer:

EGType: SASection: 1-/

+1)

What ind of molecular orbital E5 EG5 F5 or FG) results when the two atomic orbitals shown below interact in themanner indicated!

Answer:

EType: SA

Section: 1-/


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+2)


manner indicated!

Answer:

FType: SA

Section: 1-/

++)

What ind of molecular orbital E5 EG5 F5 or FG) results when the two atomic orbitals shown below interact in themanner indicated!

Answer:

EGType: SASection: 1-/

+0)


manner indicated!

Answer:

FGType: SA

Section: 1-/

+")

%hoose the correct hybridiBation for the atom indicated in the molecule below.

%,+%,2%,2%,+


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H

A)

sp

$)

sp2

%)

sp+

')

none of the abo3e

Answer:

%Type: *%

Section: 1-4

+/)

What orbitals are used to form the co3alent bonds in butane %,+%,2%,2%,+)!

Answer:

The carbon-carbon E bonds are formed by the o3erlap of two carbon sp+hybrid atomic orbitals. The carbon-

hydroen E bonds are formed by the o3erlap of a carbon sp+hybrid atomic orbital and a hydroen s orbital.



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+4)

Which carbons) in the followin molecule is are) sp hybridiBed!

A)

carbon 1

$)

carbon 2

%)

carbons 15 +

')

carbons 0

()

carbon 05 "Answer:

(Type: *%

Section: 1-9

+)

Which of the followin is an sp2hybridiBed carbon!

A)

$)

I %,+

%)

')


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A and $

()

A5 $ and %

Answer:

AType: *%

Section: 1-1

+9)

What is the predicted shape5 bond anle5 and hybridiBation for 7%,+!

A)

trional planar5 12J5 sp2

$)

trional planar5 12J5 sp+

%)

trional planar5 19."J5 sp2

')

trional pyramidal5 12J5 sp2

()

trional pyramidal5 19."J5 sp2

Answer:

AType: *%

Section: 1-1

0)

What orbitals o3erlap to create the ,-% bond in %,+7!

A)

sp+-sp+$)

sp2-sp+

%)

s-p


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')

s-sp2

()

s-sp+

Answer:

'Type: *%

Section: 1-1


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01)

The lone-pair electrons of the methyl anion occupy a __________ orbital.

A)

s

$)

p

%)

sp

')

sp2

()

sp+

Answer:

(Type: *%

Section: 1-1

02)

Which of the followin is closest to the %--% bond anle in %,+--%,+!

A)

1J

$)

12J

%)

19."J

')

9J

()

1/J

Answer:

%Type: *%


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Section: 1-11

0+)

(ach lone pair of electrons on the atom in methanol %,+,) occupies an) __________ orbital.

A)

s

$)

p

%)

sp

')

sp2

()

sp+

Answer:

(Type: *%

Section: 1-11

00)

The &-, sinle bond in methyl amine %,+&,2) is a __________ bond formed by the o3erlap of a __________

orbital on & and a __________ on ,.

A)

EK sp2K s

$)

E K sp+K s

%)

F K sp+K s

')

F K sp2K p

()

F K p K p

Answer:


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$Type: *%

Section: 1-12

0")

Triethylamine L%,+%,2)+&M is a molecule in which the nitroen atom is __________ hybridiBed and the %&%

bond anle is __________.

A)

sp25 N19."J

$)

sp25 O19."J

%)

sp+5 N19."J')

sp+5 O19."J

()

sp5 19."J

Answer:

'Type: *%

Section: 1-12


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0/)

The &-, bond in the ammonium ion5 &,075 is formed by the o3erlap of what two orbitals!

A)

sp+-sp+$)

sp+-sp2

%)

sp2-sp2

')

sp2-s()

sp+-sAnswer:


04)

Amon the hydroen halides5 the stronest bond is found in __________ and the lonest bond is found in

__________.A)

,#5 ,#$)

,#5 ,8%)

,85 ,#

')

,85 ,8()

,%l5 ,$r

Answer:


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$Type: *%

Section: 1-1+

0)

Which bond in the followin molecule is the shortest!

A)

bond 1

$)

bond 2 %)

bond +

')

bond 0

()

bond "Answer:


09)

Which of the followin species ha3e tetrahedral bond anles!

A)

A5 ' and ($)

A5 '5 ( and #%)


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A and (

')

' only

()

A5 $ and (

Answer:

$Type: *%

Section: 1-10


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")

The carbon-carbon double bond in ethene is __________ and __________ than the carbon-carbon triple bond in

ethyne.A)

stronerK shorter$)

stronerK loner%)

weaerK shorter')

weaerK loner

()

stronerK more polar

Answer:


"1)

What is the %&& bond anle in the compound shown below!

A)

P/J

$)

P9J%)

P11J

')

P12J

()


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P1J

Answer:

'Type: *%

Section: 1-10

"2)

'raw the structure of a molecule which contains only carbon and hydroen atoms only three of which are carbon)

and in which two of the carbons are sp2hybridiBed and the other is sp hybridiBed.

Answer:

,2%%%,2Type: SA

Section: 1-10

"+)

Why is the %, bond in ethene ,2%%,2) shorter and stroner than the %, bond in ethane%,+%,+)!

Answer:

The lenth and strenth of a %, bond depends on the hybridiBation of the carbon atom. The morescharacter inthe hybrid orbital used by carbon to form the bond5 the shorter and stroner the bond. This is because an s orbital is

closer to the nucleus than is ap. (thene uses carbonsp2hybrid orbitals 1Q+scharacter) to mae its carbon-

hydroen bonds while ethane uses carbonsp+1Q0scharacter).Type: SASection: 1-10

"0)

Which of the followin molecules does not ehibit a net dipole moment of Bero!

A)

%2

$)

%,0

%)

%%l0')

,2

()

S+


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'Type: *%

Section: 1-1"


31/159

"")

Which of the followin molecules has a net dipole moment of Bero!

A)

$)

%)

')

()

Answer:

$Type: *%

Section: 1-1"


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"/)

Which of the followin molecules has the smallest dipole moment!

A)

$r2 $)

&,+

%)

,%l

')

,$r

()

,8

Answer:

AType: *%

Section: 1-1"


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"4)

$#+has a dipole moment of Bero. =ropose a structure for $#+that is consistent with this information.

Answer:

$#+is trional planar.

Type: SA

Section: 1-1"

")

'raw the 6eul structure and show the direction of the dipole moment for %,2%l2.Answer:

Type: SASection: 1-1"

"9)

Which of the followin is not a conRuate acid-base pair!

A)

,25 ,-

$)

,25 ,+7

%)

,S0-5 ,2S0

')

-,5 2-

()


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&+-5 &2

-

Answer:

(Type: *%

Section: 1-1/

/)

What is the product formed from the followin acid-base reaction!

A)

%,+-7 7&,0

$)

%,2, 77&,+

%)

%,+,277 -&,2

')

%,+&,27 ,2

()

%,07 &,2,

Answer:

AType: *%

Section: 1-1/


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/1)

The conRuate acid of ,2 is:

A)

,+-$)

,+

%)

,+7

')

,-

()

,27

Answer:

%Type: *%Section: 1-1/

/2)

Which of the followin ions is the stronest acid!A)

,-

$)

,-

%)

,S0-

')

,2

()

,+7

Answer:


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(Type: *%

Section: 1-1/

/+)

Which species act as bases in the followin reaction!

A)

1 and 2

$)

+ and 0

%)

2 and 0

')

1 and +

()

2 and +

Answer:

%Type: *%Section: 1-1/

/0)

What is the conRuate acid of &,+!

A)

7&,+

$)

-&,

%)

7&,0

')


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-&,2

()

7&,2

Answer:

%Type: *%

Section: 1-1/


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/")

What is the conRuate acid of %,+&,2!

A)

%,+&,+7$)

%,+&,-

%)

&,07

')

&,2-Answer:

AType: *%

Section: 1-1/

//)

What is the conRuate base of %,+&,2!

A)

%,+&,+7

$)

%,+&,-

%)

&,07

')

&,2-

Answer:

$Type: *%

Section: 1-1/

/4)


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i3e the conRuate acid and the conRuate base for ,S0-.

Answer:

conRuate acid: ,2S0

conRuate base: S02-

Type: SA

Section: 1-1/

/)

Write a completed e>uation for the acid-base pair shown below.

,%2, 7-&,2

Answer:

,%2, 7-&,2 ,%2

-7 &,+

Type: SA

Section: 1-1/

/9)

What is the p, of a .1 * solution of ,%l! &ote: p6afor ,%l is -/.)

A)

/

$)

-/

%)

1

')

-

()

-1Answer:

%Type: *%Section: 1-14

4)

8f ,2 has a p6a3alue of 1".4 and ,# has a p6a3alue of +.25 which is a stroner base5 ,-or #-! (plain.


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,-is a stroner base than #-because ,# is a stroner acid than ,25 and the stroner the acid the weaer its

conRuate base.Type: SA

Section: 1-14


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41)

Which of the followin is the stronest acid!

A)

%,+,

$)

%,+,27

%)

,2&-

')

%,+&,2()

%,+&,+7

Answer:


42)

The p6a of %,+%, is 0. and the p6a of ,%, is +.. i3en this information5 one nows that __________.

A)

%,+%, completely ioniBes in water

$)

,%, is a weaer acid than %,+%,

%)

,%-is a weaer base than %,+%-

')

%,+%, reacts with ,-while ,%, does not

()

,%, reacts with ,-while %,+%, does not

Answer:


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%Type: *%

Section: 1-2

4+)


A)

,#

$)

,2

%)

:&,+

')

%,0()

%,+,

Answer:

AType: *%

Section: 1-2

40)


A)

%,+%,2,

$)

%,+%,+

%)

%,+&,%,+

')

%,+%%,

()

%,+%,%,2


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AType: *%

Section: 1-2


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4")

%onsider the set of compounds5 &,+5 ,#5 and ,2. Uan these compounds in order of increasin acidity and

discuss your rationale.Answer:

&,+O ,2 O ,#

When determinin relati3e acidity5 it is often useful to loo at the relati3e basicity of the conRuate bases. The

stroner the acid5 the weaer more stable5 less reacti3e) the conRuate base. 8n this case5 one would loo at the

relati3e basicity of #-5 ,-5 and &,2-. The relati3e strenths of these species can be aued based on the

electroneati3ity of the chared atom in each base. Since fluorine is the most electroneati3e5 #-is the most stable5

least reacti3e base in the roup. This means that its conRuate acid5 ,#5 is the stronest.Type: SASection: 1-2

4/)


A)

8$)

88

%)

888')

8V()


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V

Answer:

(Type: *%

Section: 1-21

44)

(plain why :+is a weaer base than :&,+.

Answer:

#luorine has an electron withdrawin effect that reduces the a3ailability of the pair of electrons on nitroen. Thusthe basicity of :+is less than that of :&,+.

Type: SA

Section: 1-21


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4)

Would you predict trifluoromethanesulfonic acid5 %#+S+,5 to be a stroner or weaer acid than methanesulfonic

acid5 %,+S+,! (plain your reasonin.

Answer:

Trifluoromethanesulfonic acid is a stroner acid. %ompare the strenths of the conRuate bases and remember thatthe weaer the base5 the stroner the conRuate acid. 8n the case of the trifluoro deri3ati3e5 the presence of the hihly

electroneati3e fluorine atoms ser3es to delocaliBe the neati3e chare to a reater etent. This additional

delocaliBation maes trifluoromethanesulfonate a weaer base.Type: SASection: 1-21

49)

Which of the followin anions5 %,+%,$r%2- or %,+%,#%2

-is the stroner base! (plain your choice.

Answer:

%,+%,$r%2-is the stroner base. The more electroneati3e # atom can more effecti3ely delocaliBe the neati3e

chare 3ia induction. This reater delocaliBation stabiliBes %,+%,#%2- relati3e to %,+%,$r%2-and maes it

a weaer base.Type: SA

Section: 1-21

)

The p6a of %,+%, is 0.. 8f the p, of an a>ueous solution of %,+%, and %,+%-is 0.5 then one

nows __________.

A)

%,+%, is completely ioniBed

$)

L%,+%,M N L%,+%-M

%)

L%,+%,M L%,+%-M

')

L%,+%,M O L%,+%-M

()

%,+%, is completely unioniBed

Answer:

%


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1)

When a small amount of heanoic acid L%,+%,2)0%2,5 p6aP0.M5 is added to a separatory funnel which

contains the oranic sol3ent diethyl ether and water with a p, of 2.5 it is found mainly in the __________ phase as__________.

A)

etherK %,+%,2)0%2-

$)

waterK %,+%,2)0%2-

%)

etherK %,+%,2)0%2,')

waterK %,+%,2)0%2,

()

none of the abo3e

Answer:

%Type: *%

Section: 1-20


48/159

2)

When a small amount of heanoic acid L%,+%,2)0%2,5 p6aP0.M5 is added to a separatory funnel which

contains the oranic sol3ent diethyl ether and water with a p, of 12.5 it is found mainly in the __________ phaseas __________.

A)

etherK %,+%,2)0%2-

$)

waterK %,+%,2)0%2-

%)

etherK %,+%,2)0%2,

')

waterK %,+%,2)0%2,

()

none of the abo3e

Answer:

$Type: *%

Section: 1-20

+)

At what p, will 2" of a compound with a p6a of ".+ be in its basic form!

Answer:

0.Type: SA

Section: 1-20

0)

The amino acid lycine ,+&7%,2%2,) has two acidic ,s5 one with p6a 2.+0 and the other with p6a 9./.

'raw the structure of the form of lycine that predominates at a p, of 12.

Answer:



49/159

")

$ufferin is used to maintain the p, of human blood in the relati3ely narrow 4.+ - 4.0 rane. What acidQbase pairser3es to buffer the blood!

A)

,2 Q ,-

$)

,+7Q ,2

%)

,2%+Q ,%+-

')

&,07Q &,+

()

,%l Q %l-

Answer:

%Type: *%

Section: 1-2"

/)

(plain why Al%l+is a Dewis acid.

Answer:

A Dewis acid is an electron pair acceptor. Aluminum in Al%l+has an empty p orbital that can accommodate the pair

of electrons pro3ided by a Dewis base.Type: SA

Section: 1-2/


50/159


Chapter 2: An Introduction to Organic Compounds

1)

Which of the followin is a tertiary amine!A)

$)

%)

')

()

Answer:


51/159

(Type: *%

Section: 2-1

2)

There are isomers that ha3e the molecular formula %",11$r. ,ow many of these are tertiary alyl bromides!

A)

$)

1%)

2')

+()

Answer:



52/159

+)

Which of the followin issec-butyl alcohol!

A)

%,+%,

2%,

2%,

2,

$)

%,+%,,)%,2%,+

%)

%,+)2%,%,2,

')

%,+)2%,,

()

%,+)2%,%,+

Answer:


0)

What is the common name for the followin structure!

A)

8sobutane

$)

8sopropylmethane

%)

t-$utane

')

n-$utane

()


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sec-$utane

Answer:

AType: *%

Section: 2-2

")

i3e the 8;=A% name for the followin structure:

A)

2-methyl-+-ethylheptane

$)

+-ethyl-2-methylheptane

%)

"-8sopropyloctane

')

0-8sopropyloctane

()

2-methyl-+-propylheptaneAnswer:


/)

There is somethin wron with the followin name. Write the structure and correct the name: 2-ethylpropane.

Answer:


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The correct name is 2-methylbutane.Type: SA

Section: 2-2

4)

i3e structures for the three isomers with molecular formula %",12and pro3ide the common name of each.

Answer:


)

=ro3ide an acceptable name for the alane shown below.

%,+%,2%,2%,2%,2%,+

Answer:

heane or n-heaneType: SASection: 2-2

9)


Answer:

25 "-dimethylheptaneType: SA

Section: 2-2

1)



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Answer:

"-sec-butyl-25 2-dimethylnonane or

25 2-dimethyl-"-1-methylpropyl) nonaneType: SASection: 2-2

11)


Answer:

0-isopropyldecane or 0-1-methlyethyl) decaneType: SA

Section: 2-2


56/159

12)


Answer:

+-ethyl-/-methyl-"-propylnonaneType: SA

Section: 2-2

1+)


Answer:

+-ethyl-05 0-dimethylheptaneType: SA

Section: 2-2

10)

'raw an acceptable structure for 0-t-butyloctane.

Answer:


1")

'raw an acceptable structure for +-ethyl-+-methylheane.

Answer:


57/159


1/)

'raw an acceptable structure for 0-isopropyl-2-methylheptane.Answer:

Type: SA

Section: 2-2


58/159

14)

'raw an acceptable structure for /-ethyl-25 /5 4-trimethyl-"-propylnonane.

Answer:

Type: SA

Section: 2-2

1)


Answer:

25 25 +5 /-tetramethylheptaneType: SASection: 2-2

19)


Answer:

/-ethyl-2-methyl-"-propyldecaneType: SASection: 2-2

2)

i3e the systematic name of the alane shown below.


59/159

Answer:

0-ethyl-25254-trimethylnonaneType: SASection: 2-2


60/159

21)

i3e the systematic name of the alane shown below.

Answer:

+-ethyl-0-isopropyloctaneType: SA

Section: 2-2

22)

i3e the systematic name of the cycloalane shown below.

Answer:

0-butyl-152-dimethylcycloheaneType: SA

Section: 2-+

2+)

'raw an acceptable structure forsec-butylcyclopentane.

Answer:

Type: SASection: 2-+

20)

=ro3ide the systematic name of the compound shown.


61/159

Answer:

0-butyl-1-ethyl-2-methylcycloheptaneType: SA

Section: 2-+


62/159

2")

What is the common name for the followin structure!

A)

8sobutyl bromide

$)

t-$utyl bromide

%)

&eobutyl bromide

')

sec-$utyl bromide

()

8sopropyl methyl bromide

Answer:

$Type: *%

Section: 2-0

2/)

i3e the 8;=A% name for the followin compound:

A)

1-chloro-2-methylcycloheane

$)

1-methyl-2-chlorocycloheane

%)


63/159

1-chloro-"-methylcycloheane

')

1-methyl-"-chlorocycloheane

()

15 2-chloromethylcycloheaneAnswer:


24)

Which of the followin is diisopropyl ether!

A)

%,+%,2%,2%,2%,2%,+

$)

%)

%,+%,

2%,

2%,%,

+)2')

%,+)+%%%,+)+

()

%,+)2%,)%,%,+)2Answer:

(Type: *%

Section: 2-"


64/159

2)

'raw all ethers with molecular formula %0,1.

Answer:

Type: SA

Section: 2-"

29)

'raw all possible constitutional isomers for %2,/ and i3e common names for each structure.Answer:

Type: SASection: 2-" and 2-/

+)

i3e the 8;=A% name for the followin structure:

A)

+-chloro-2-methylcycloheanol

$)

2-methyl-"-chlorocycloheanol

%)


65/159

1-chloro-0-methylcycloheanol

')

"-chloro-2-methylcycloheanol

()

2-methyl-+-chlorocycloheanolAnswer:

'Type: *%Section: 2-/

+1)

Which of the followin compounds does not ha3e the molecular formula %/,10!

A)

1-heanol

$)

2-heanol

%)

+-methyl-2-pentanol

')

+-methyl-+-pentanol()

cycloheanol

Answer:

(Type: *%

Section: 2-/


66/159

+2)

i3e the structure of isopentyl alcohol.

Answer:


++)

=ro3ide the systematic name of the compound shown.

Answer:

/54-dimethyl-+-octanolType: SASection: 2-/

+0)

'raw the structure of +-chloro-&-ethyl-2-heanamine.

Answer:


+")

i3e the structure of tetramethylammonium chloride.

Answer:


67/159

Type: SA

Section: 2-4


68/159

+/)

'raw the structure ofN-ethyl-"-methyl-+-heanamine.

Answer:


+4)

#luorine is more electroneati3e than chlorine yet the carbon-fluorine bond in %,+-# is shorter than %,+-%l.

(plain.Answer:

%hlorine is a larer atom than fluorine and uses a +p rather than 2p orbital. The o3erlap of a 2sp+orbital with a +p

orbital is not as ood as the o3erlap of a 2sp+orbital with a 2p orbital5 causin the bond to be loner and weaer.Type: SA

Section: 2-

+)

Which of the followin will ha3e the lowest boilin point!

A)

%,+%l

$)

%,0

%)

%,2%l2

')

%,%l+

()

%%l0

Answer:

$Type: *%


69/159

Section: 2-9

+9)

Which of the compounds below will form hydroen bonds between its molecules!

A)

%,+%,2%,2#

$)

lR%,+%,2%,2%,+%)

%,+)+&

')

%,+%,2%,+()

%,+&,%,2%,+Answer:

(Type: *%

Section: 2-9


70/159

0)

Which of the followin has the reatest 3an der WaalXs interaction between molecules of the same ind!

A)

$)

%,+%,2%,2%,+%)

')

%,+%,2%,2%,2%,+

()

Answer:


01)

Which of the followin has the lowest boilin point!A)

%,+%,2%,2%,2%,2%,+$)


71/159

%)

')

()

%,+%,2%,2%,2%,2%,2%,+Answer:



72/159

02)

Which of the followin has the reatest solubility in %,+%,2%,2%,+!

A)

%,+,$)

%,+-&a7

%)

%,+&,2')

%,+%,+()

%,+)+%,

Answer:


0+)

Which of the followin is the most soluble in ,2!

A)

%,+%,+

$)

%,+%,2,

%)

%,+%,2%l

')

%,+%,2%,+

()

%,+%,

Answer:


73/159

$Type: *%

Section: 2-9

00)

Which of the followin would ha3e the hihest boilin point!

A)

%,+%,2%,2%,2%,+$)

%,+%,2%,2%,2%,+%)

,%,2%,2%,2%,2,

')

%,+%,2%,2%,2%,+

()

Answer:


0")

%onsider the three isomeric alanes n-heane5 25 +-dimethylbutane5 and 2-methylpentane. Which of the followincorrectly lists these compounds in order of increasin boilin point!

A)

25 +-dimethylbutane O 2-methylpentane O n-heane

$)

2-methylpentane O n-heane O 25 +-dimethylbutane

%)

2-methylpentane O 25 +-dimethylbutane O n-heane

')


74/159

n-heane O 2-methylpentane O 25 +-dimethylbutane

()

n-heane O 25 +-dimethylbutane O 2-methylpentaneAnswer:

AType: *%

Section: 2-9

0/)

What is the stronest intermolecular force present in li>uid ethanol!

A)

induced dipole-induced dipole

$)

dipole-dipole5 specifically hydroen bondin%)

dipole-dipole5 but not hydroen bondin

')

ion-dipole

()

ion-ion

Answer:

$Type: *%

Section: 2-9

04)

Assumin rouhly e>ui3alent molecular weihts5 which of the followin would ha3e the hihest boilin point!A)

a tertiary amine$)

a >uaternary ammonium salt%)

an alcohol')


75/159

an ether

()

an alyl chlorideAnswer:


0)

(plain why has a lower boilin point than %,+%,2%,2%,+.

Answer:

%,+%,2%,2%,+has reater 3an der Waals forces because it has a reater contact area than isobutane. Therefore5the boilin point of %,+%,2%,2%,+is hiher.

Type: SA

Section: 2-9

09)

=rimary and secondary amines ehibit hydroen bondinK tertiary amines do not. (plain.Answer:

The nitroen in a tertiary amine is not attached to a hydroen. Uecall that for a molecule to ehibit hydroenbondin it must ha3e a hydroen attached to a hihly electroneati3e atom such as #5 &5 or .


")

(plain why trimethylamine5 %,+)+&:5 has a considerably lower boilin point than propylamine

%,+%,2%,2&,25 e3en thouh both compounds ha3e the same molecular formula.

Answer:

Since hydroen bondin is possible for propylamine and not for trimethylamine5 the boilin point is hiher for

propylamine.Type: SA

Section: 2-9

"1)

Which of the molecules below has the hiher boilin point! $riefly eplain your choice.

%,+%,2%,2, or %,+%,2%,+

Answer:


76/159

%,+%,2%,2, has the hiher boilin point since it is capable of intermolecular hydroen bondin.

Type: SA

Section: 2-9

"2)

Would you epect sodium chloride &a%l) to be hihly soluble in the oranic sol3ent heane%,+%,2%,2%,2%,2%,+)! $riefly eplain your answer.

Answer:

ne would not epect &a%l to be hihly soluble in heane. &a%l is an ionic solid i.e.5 a 3ery polar material) while

heane is nonpolar. &onpolar sol3ent molecules do not sol3ate ions well. The attractions of oppositely chared ions

to each other are 3astly reater than the wea attractions of the ions for the sol3ent.Type: SASection: 2-9


77/159

"+)

Which compound is more soluble in water! $riefly eplain your choice.

%,+%,+ or %,+%,2,

Answer:

%,+%,2, is more soluble in water since it can donate a hydroen bond to water and accept a hydroen bond

from water. %,+%,+can only accept a hydroen bond from waterK it has no hydroen which can hydroen bond

to water.Type: SASection: 2-9

"0)

Which compound is more soluble in water! $riefly eplain your choice.

%,+)2&, or %,+%,2%,+

Answer:

%,+)2&, is more soluble in water since it can hydroen bond with water. Alanes are not capable of hydroen

bondin with water.Type: SA

Section: 2-9

"")

Which intermolecular force is primarily responsible for the interactions amon alane molecules!

Answer:

Van der WaalXs or Dondon forcesType: SA

Section: 2-9

"/)

What is polariBability and how is it related to the siBe of an atom!Answer:

=olariBability indicates the ease with which an electron cloud can be distorted. The larer the atom5 the more looselyits nucleus holds the electrons in its outermost shell5 and the more they can be distorted.

Type: SA

Section: 2-9

"4)

Arrane the followin amines in order of increasin boilin point5 lowest bp to hihest bp:%,+)2%,%,2%,2&,25 %,+)2%,&%,+)25 and %,+)2%,%,2&,%,+.

Answer:


78/159

%,+)2%,&%,+)2O %,+)2%,%,2&,%,+O %,+)2%,%,2%,2&,2Type: SA

Section: 2-9

")

The eclipsed and staered forms of ethane are said to differ in:A)

molecular formula.$)

confiuration.%)

conformation.')

constitution.()

structure.

Answer:



79/159

"9)

Which of the followin is the staered conformation for rotation about the %1%2bond in the followin structure!

A)

8

$)

88

%)

888

')

8V

()

V

Answer:

A


/)

Amon the butane conformers5 which occur at enery minima on a raph of potential enery 3ersus dihedral anle!

A)


80/159

auche only

$)

eclipsed and totally eclipsed

%)

auche and anti

')

eclipsed only

()

anti onlyAnswer:

%


/1)

Which of the followin best eplains the relati3e stabilities of the eclipsed and staered forms of ethane! The

__________ form has the most __________ strain.A)

eclipsedK steric$)

eclipsedK torsional%)

staeredK steric')

staeredK torsionalAnswer:



81/159

/2)

Which of the followin best eplains the reason for the relati3e stabilities of the conformers shown!

A)

8 has more torsional strain.

$)

8 has more steric strain.

%)

88 has more torsional strain.

')

88 has more steric strain.

Answer:

'Type: *%

Section: 2-1

/+)

Which of the followin statements about the conformers that result from rotation about the %2-%+ bond of butane is

correct!

A)

The hihest enery conformer is one in which methyl roups are eclipsed by hydroens.

$)

The auche conformer is an eclipsed one.

%)

Steric strain is absent in the eclipsed forms.

')


82/159

Torsional strain is absent in the eclipsed forms.

()

none of the abo3eAnswer:


/0)

'raw the &ewman proRection that represents the most stable conformation of +5+-dimethylheane 3iewed alon the

%+-%0 bond.Answer:

Type: SA

Section: 2-1

/")

'raw the &ewman proRection that represents the least stable conformation of +5+-dimethylheane 3iewed alon the

%+-%0 bond.

Answer:

Type: SA

Section: 2-1

//)

'raw the &ewman structure for the most stable conformation of 1-bromopropane considerin rotation about the %1-

%2bond.

Answer:


83/159

Type: SA

Section: 2-1

/4)

'raw a &ewman proRection of the most stable conformation of 2-methylpropane.

Answer:

Type: SA

Section: 2-1

/)

'efine the term conformation.Answer:

%onformations are different arranements of the same molecule formed by rotations about sinle bonds.Type: SASection: 2-1

/9)

;se a sawhorse structure to depict the eclipsed conformer of ethane.

Answer:


4)


84/159

View a butane molecule alon the %2-%+bond and pro3ide a &ewman proRection of the lowest enery conformer.

Answer:

Type: SA

Section: 2-1

41)

=ro3ide a representation of the auche conformer of butane.

Answer:


42)

'raw the &ewman proRection of the most stable conformation that results due to rotation about the %2-%+bond in

25+-dimethylbutane.

Answer:


4+)


85/159

Which of the followin correctly rans the cycloalanes in order of increasin rin strain per methylene!

A)

cyclopropane O cyclobutane O cycloheane O cycloheptane

$)

cycloheane O cyclopentane O cyclobutane O cyclopropane

%)

cyclopentane O cyclobutane O cyclopentane O cyclopropane

')

cyclopentane O cyclopropane O cyclobutane O cycloheane

()

cyclopropane O cyclopentane O cyclobutane O cycloheane

Answer:



86/159

40)

'escribe the source of anle strain and torsional strain present in cyclopropane.

Answer:

The anle strain arises from the compression of the ideal tetrahedral bond anle of 19."J to /J. The lare torsional

strain occurs since all %-, bonds on adRacent carbons are eclipsed.Type: SASection: 2-11

4")

Which of the followin correctly lists the conformations of cycloheane in order of increasin enery!

A)

chair O boat O twist-boat O half-chair

$)

half-chair O boat O twist-boat O chair

%)

chair O twist-boat O half-chair O boat

')

chair O twist-boat O boat O half-chair

()

half-chair O twist-boat O boat O chair

Answer:

'Type: *%

Section: 2-12

4/)

Which of the followin is the most stable conformation of bromocycloheane!


87/159

A)

8

$)

88%)

888

')

8V

()

V

Answer:


44)

8n the boat conformation of cycloheane5 the YflapoleY hydroens are located:A)

on the same carbon.$)

on adRacent carbons.%)

on %-1 and %-+.')


88/159

on %-1 and %-0.

()




89/159

4)

Which conformer is at a local enery minimum on the potential enery diaram in the chair-chair intercon3ersion of

cycloheane!A)

half-chair$)

planar%)

boat')

twist-boat

()

fully eclipsed

Answer:


49)

'raw the chair conformer of cycloheane. Dabel the aial hydroens ,a) and the e>uatorial hydroens ,e).

Answer:

Type: SA

Section: 2-12

)

The 6e>for the intercon3ersion for the two chair forms of methylcycloheane at 2" J% is 1. What of the chair

conformers feature an aial methyl roup!A)

9"$)


90/159

4"

%)

"

')

2"

()

"Answer:

(Type: *%Section: 2-1+

1)

The e>uilibrium constant for the rin-flip of fluorocycloheane is 1." at 2" J%. %alculate the percentae of the aial

conformer at the temperature.Answer:

6e> 1."

aial 1

1

0Type: SA

Section: 2-1+


91/159

2)

Which of the followin describes the most stable conformation of trans-1-tert-butyl-+-methylcycloheane!

A)

$oth roups are e>uatorial.

$)

$oth roups are aial.

%)

The tert-butyl roup is e>uatorial and the methyl roup is aial.

')

The tert-butyl roup is aial and the methyl roup is e>uatorial.

()

none of the abo3e

Answer:

%Type: *%

Section: 2-10

+)

&ame the compound shown below.

A)

trans-152-dichlorocycloheane

$)

cis-152-dichlorocycloheane

%)

trans-15+-dichlorocycloheane')

cis-15+-dichlorocycloheane

()

trans-150-dichlorocycloheane

Answer:


92/159

'Type: *%

Section: 2-10

0)

Which of the followin has two e>uatorial alyl substituents in its most stable conformation!

A)

151-dimethylcycloheane

$)

cis-152-dimethylcycloheane

%)

cis-15+-diethylcycloheane

')

cis-150-diethylcycloheane

()

trans-15+-diethylcycloheane

Answer:

%Type: *%

Section: 2-10

")

'raw the most stable conformation of trans-1-tert-butyl-+-methylcycloheane.

Answer:

Type: SA

Section: 2-10

/)

'raw the most stable conformer of cis-1-isopropyl-2-methylcycloheane.Answer:


93/159



94/159

4)

'raw the most stable conformation of cis-1-isopropyl-2-methylcycloheane.

Answer:

Type: SA

Section: 2-10

)

,ow many constitutional isomers are possible for %/,10!

A)

0

$)

"

%)

/

')

4

()

Answer:

$Type: *%

Section: 9

9)

8f an acyclic alane hydrocarbon contains n carbon atoms5 how many hydroen atoms must it also contain!

A)

n

$)

n 7 2


95/159

%)

n - 2')

2n

()

2n 7 2

Answer:

(Type: *%

Section: 9


96/159


Chapter 3: Alenes ! "hermod#namics and $inetics

1)

What is the molecular formula of the hydrocarbon that contains " carbon atoms5 one rin5 and one F bond!Answer:

%",Type: SASection: +-1

2)

What is the molecular formula of the hydrocarbon that contains carbon atoms5 one rin5 and two F bonds!

Answer:

%,12Type: SASection: +-1

+)

What is the common name for the followin compound!

A)

t-butylene$)

sec-butylene%)

isobutylene')

butylene()

methylpropylene

Answer:

%


97/159

Type: *%Section: +-2

0)

What is the 8;=A% name for the followin compound!

A)

2-methyl-1-butene

$)

isopentene%)

2-methybutene

')

2-ethylpropene

()

+-methyl-+-butene

Answer:

AType: *%

Section: +-2


98/159

")

What is the 8;=A% name for the followin compound!

A)

"-methylcycloheene

$)

0-methylcycloheene

%)

1-methyl-+-cycloheene

')

1-methyl-0-cycloheene

()

methylcycloheeneAnswer:

$Type: *%

Section: +-2

/)

Which of the followin is 3inyl chloride!

A)

%,+%,2%l

$)

%,2%,%,2%l

%)

%,2%,%l

')


99/159

()

Answer:

%Type: *%

Section: +-2

4)

Which of the followin is an allylic alcohol!

A)

%,2%,%,2%,+

$)

%,2%,%,2%,+

%)

,%,%,%,2%,+

')

%,+%,%,%,2,

()

%,2%,%,2%,2,

Answer:

'Type: *%

Section: +-2

)

=ro3ide the proper 8;=A% name for the alene shown below.


100/159

E)-+50-dimethyl-+-hepteneType: SA

Section: +-2

9)

=ro3ide the proper 8;=A% name for the alene shown below.

Answer:

/-bromo-1-methylcycloheeneType: SA

Section: +-2

1)

'raw and name the si alenes which ha3e the molecular formula %",1.

Answer:

Type: SA

Section: +-2

11)

=ro3ide the systematic name of the alene below.

Answer:

2-ethyl-1-heeneType: SA

Section: +-2


101/159

12)

=ro3ide the systematic name of the compound below.

Answer:

"-isobutyl-1-methylcyclopenteneType: SA

Section: +-2


102/159

1+)

Which of the followin statements about ethene5 %2,05 is incorrect!

A)

The ,-%-, bond anles are approimately 19."J.$)

All of the hydroen atoms are in the same plane.

%)

There is a total of fi3e sima bonds.

')

The carbon atoms are sp2hybridiBed.

()

The ,-%-, bond anles are approimately 12J.

Answer:

AType: *%

Section: +-+

10)

Which of the followin statements about propene5 %,+%,%,25 is correct!

A)

All nine atoms lie in the same plane.

$)

The compound has a cis and trans isomer.

%)

8t enerally acts as a Dewis acid.

')

There is a total of eiht sima bonds.

()

All the carbon atoms are sp2hybridiBed.

Answer:

'


103/159

Type: *%Section: +-+

1")

'raw the structure of propyl 3inyl ether.

Answer:

Type: SA

Section: +-+

1/)

Which of the followin is capable of ehibitin cis-trans isomerism!

A)

1-butene

$)

1-pentene

%)

cycloheene

')

ethene ()

2-butene

Answer:

(Type: *%

Section: +-0

14)

'raw all the possible constitutional isomers of %0,.

Answer:


104/159

Type: SASection: +-0


105/159

1)

'raw the structure of two alenes with molecular formula %0,that do not ehibit cis-trans isomerism.

Answer:


19)

Which of the followin best describes the eometry about the carbon-carbon double bond in the alene below!

A)

E

$)

Z

%)

neitherEnorZ

Answer:

%Type: *%

Section: +-"

2)

Assin the ( or Z confiuration to the followin molecule:

Answer:

The molecule has a Z confiuration based on the priority rule established by %ahn-8nold-=relo.


106/159

Type: SASection: +-"

21)

'raw the structure of Z)-0-ethyl-+-methylheptene.9.

Answer:

Type: SA

Section: +-"

22)

'raw the structure of Z)-0-ethyl-+5/-dimethyl-+-heptene.

Answer:

Type: SA

Section: +-"

2+)

Which of the followin is not an electrophile!

A)

,7


107/159

$)

$#+%)

7&2

')

#e7+

()

%,2%,2Answer:

(

Type: *%Section: +-/

20)

Which of the followin is not a nucleophile!

A)

#e$r+

$)

$r-%)

&,+')

()

%,+%,+Answer:

AType: *%

Section: +-/

2")


108/159

'raw the cur3ed arrows to show how %,+%,%,%,+reacts with ,$r to form a carbocation.

Answer:

Type: SASection: +-/


109/159

2/)

What is the 3alue of [, in calQmole for the reaction shown!

%,+)+%, 7 %l%l %,+)+%%l 7 ,%l

$ond eneries are: %,+)+%

, 91 calQmole%,+)+%%l 4." calQmole

%l%l " calQmole

,%l 1+ calQmole

A)

7+2."

$)

-"4."

%)

-+2."

')

7"4."

()

-."

Answer:

% Type: *%Section: +-4

24)

,ow many transition states are present in the followin reaction diaram!

A)

+

$)


110/159

0

%)

"

')

2

()

1Answer:

'Type: *%Section: +-4

2)

An increase in which of the followin results in a decrease in the rate of the chemical reaction!

A)

temperature

$)

concentration

%)

collision fre>uency')

enery of acti3ation

()

fraction of collisions with proper orientation

Answer:

'Type: *%

Section: +-4


111/159

29)

An increase in which of the followin will occur if the reaction temperature is increased!

8. (nery of acti3ation88. %ollision fre>uency

888. #raction of collisions with sufficient enery

A)

8 and 88

$)

8 and 888

%)

88 and 888

')

85 885 and 888

()

8

Answer:

%Type: *%

Section: +-4

+)

What is the acti3ation enery for the reaction $ A in the followin diaram!

A)

A

$)

$

%)


112/159

%

')

'()

(

Answer:

(Type: *%Section: +-4

+1)

Which of the followin contributes to mae [J more neati3e!

A)

use of a catalyst$)

a more positi3e [,J

%)

a more positi3e [SJ

')

a larer rate constant

()

none of the abo3e

Answer:

%Type: *%

Section: +-4

+2)

Which of the followin correctly describes intermediates andQor transition states!A)

Transition states occur at minima on reaction coordinate diarams.$)

$oth transition states and intermediates occur at maima on reaction coordinate diarams.%)


113/159

An intermediate is always produced after the rate-determinin step of a reaction mechanism.

')

Transition states ha3e partially formed bonds whereas intermediates ha3e fully formed bonds.

()




114/159

++)

Which of the followin correctly describes the reaction shown!

A)

[,J N and [SJ N

$)

[,J N and [S O

%)

[,J O and [S N

')

[,J O and [S O

()

[,J [S Answer:


+0)

The Arrhenius e>uation models how the rate constant __________.

A)

increases as both (aand T increase

$)

increases most when (aincreases and T decreases

%)

increases most when (adecreases and T increases

')

increases as both (aand T decrease

()

increases as reactant concentrations increaseAnswer:


115/159

%Type: *%

Section: +-4

+")

Which of the followin correctly describes the reaction whose reaction coordinate diaram is shown!

A)

enderonic with no transition state

$)

eeronic with no transition state

%)

enderonic with a transition state

')

eeronic with a transition state

()

enderonic with an intermediate

Answer:

'

Type: *%Section: +-4

+/)

;nder what conditions is [J e>ual to [,J for a chemical reaction!

Answer:

Since [J [,J - T[SJ5 then [J is e>ual to [,J when T[SJ is Bero.


116/159



117/159

+4)

i3en an acti3ation enery of 1" calQmol5 use the Arrhenius e>uation to estimate how much faster the reaction will

occur if the temperature is increased from 1 J% to 12 J%. U 1.94 calQmol I 6.Answer:

The reaction will occur about 2. times faster.Type: SASection: +-4

+)

%onsider the con3ersion of % to ' 3ia a one-step mechanism. The acti3ation enery of this con3ersion is + calQmol.

The enery difference between ' and the transition state of the reaction is 4 calQmol. (stimate [,J for the reaction% '.

Answer:

0 calQmol


+9)

%onsider the one-step con3ersion of # to . i3en that the reaction is enderonic by " calQmol and that the enerydifference between and the transition state for the process is 1" calQmol5 setch a reaction-enery profile for this

reaction. *ae sure to show how the i3en enery differences are consistent with your setch.

Answer:



118/159

0)

The [J for the con3ersion of YaialY isopropylcycloheane to Ye>uatorialY isopropylcycloheane is -2.1 calQmol.

%alculate the percentae of isopropylcycloheane molecules that ha3e the isopropyl substituent in the aial positionat this temperature.

LU 1.94 @ 1-+cal mol-16-1M

Answer:

[J -UTln6

-2.1 calQmol -1.94 @ 1-+cal mol-16-1)296)ln6

ln6

6 +0.4

aial @ 1

@ 1

2.Type: SASection: +-4

01)

What is the free enery of acti3ation of a one-step reaction! ,ow is it qualitativelyrelated to the rate constant of the

reaction!

Answer:

The free enery of acti3ation of a one-step reaction is the difference in free enery between the transition state and

the reactants. As the free enery of acti3ation increases5 the rate constant decreases.Type: SASection: +-4

02)

$ased on the followin enery diaram5 which compound5 A or %5 is formed faster from $! Which is more stable5 A

or %! (plain.

Answer:


119/159

A is formed faster since the pathway for its formation has the smaller acti3ation enery. % is more stable than A

because it has a lower enery.Type: SA

Section: +-4


120/159

0+)

%onsider the sinle step intercon3ersion of A and $ shown below. ,ow is the e>uilibrium constant 6 related to the

rate constants 1and -1and to the amounts of A and $ present at e>uilibrium!

Answer:

6 Type: SA

Section: +-4

00)

Why do reactions tend to proceed at a faster rate as T increases!

Answer:

The fraction of molecular collisions that possess sufficient enery to o3ercome the barrier to reaction increases.Type: SA

Section: +-4

0")

%onsider the reaction coordinate diaram shown. Which step has the reatest acti3ation enery!

A)

A oin to %

$)


121/159

% oin to (

%)

( oin to

')

( oin to %

()

% oin to AAnswer:

'Type: *%Section: +-


122/159

0/)

%onsider the reaction coordinate diaram shown. Which letters desinate intermediates!

Answer:

% and (Type: SA

Section: +-

04)

%onsider the reaction coordinate diaram shown. Which step has the reatest rate constant in the forward direction!

Answer:

Step + ( oin to )Type: SA

Section: +-


123/159

0)

%onsider the reaction coordinate diaram shown. What is the rate-determinin step in the con3ersion of A to !

Answer:

Step 2 % oin to ()Type: SA

Section: +-

09)

%onsider the reaction coordinate diaram shown. Which letters desinate transition states!

Answer:

$5 '5 and #Type: SA

Section: 9


124/159


Chapter %: &eactions o' Alenes

1)

%omplete the followin reaction and pro3ide a detailed5 step-by-step mechanism for the process.

Answer:

Type: SA

Section: 0-1

2)

Which of the followin is the most stable carbocation!

A)

8$)

88%)


125/159

888

')

8V

()

VAnswer:



126/159

+)

Which of the followin alenes reacts with ,%l at the slowest rate!

A)

$)

%)

')

()

Answer:


0)

What is hyperconRuation5 and how does it affect carbocation stability!

Answer:


127/159

'elocaliBation of electrons by the o3erlap of a E bond with an empty p orbital is hyperconRuation. This effect

occurs only when the interactin orbitals are properly alined. The more alyl roups which are substituents of a

cationic carbon5 the more the cation can be stabiliBed by the delocaliBin hyperconRuation effects.Type: SA

Section: 0-2

")

Accordin to the ,ammond =ostulate5 which of the followin is correct!

A)

The transition state of an endothermic reaction step will be more reactant-lie than product-lie.

$)

The intermediate of an endothermic reaction step will be more reactant-lie than product-lie.

%)

The transition state of an eothermic reaction step will be more reactant-lie than product-lie.')

All transition states are more product-lie than reactant-lie.

()

All transition states are more reactant-lie than product-lie.

Answer:

%Type: *%

Section: 0-+


128/159

/)

Which of the followin compounds will react most rapidly with ,%l!

A)

"-methyl-1-heene

$)

0-methyl-1-heene

%)

()-"-methyl-2-heene

')

()-2-methyl-+-heene

()

2-methyl-2-heene

Answer:

(Type: *%

Section: 0-+

4)

#or an enderonic reaction step5 the ,ammond postulate allows one to say that __________.

A)

the transition state of the step resembles the reactants of the step

$)

the transition state of the step resembles the products of the step

%)

the step is rate-determinin since it has the smallest (a

')

the reaction containin this step is o3erall first order

()

the transition state is precisely symmetric with bond-breain and bond-formin occurrin to the same etent

Answer:

$Type: *%


129/159

Section: 0-+

)

$ased on the relati3e stabilities of the intermediates in3ol3ed5 eplain the basis for *aro3nio3Xs rule in the

addition of hydroen halides to alenes.

Answer:

The rate-determinin step in this reaction is the production of a carbocation intermediate. Since this step is

endothermic5 ,ammondXs postulate allows one to aue the relati3e stabilities of the transition states by comparin

the relati3e stabilities of the carbocation intermediates. The reaction pathway which produces the more substitutedcarbocation will thus occur more rapidly.

Type: SA

Section: 0-+


130/159

9)

=ropose a mechanism for the followin reaction:

Answer:

Type: SA

Section: 0-/

1)

'raw the maRor oranic product enerated in the reaction below.

Answer:


131/159

Type: SA

Section: 0-0


132/159

11)


Answer:


12)


Answer:


1+)


Answer:

Type: SA


133/159

Section: 0-0

10)


Answer:

Type: SA

Section: 0-0

1")


Answer:

Type: SA

Section: 0-0

1/)

'raw the structures of the two alenes that react with ,$r to yield 1-bromo-1-methylcyclopentane as the maRororanic product.

Answer:


134/159

Type: SA

Section: 0-0

14)

Which is more hihly reioselecti3e the addition of ,%l to methylenecycloheane or to 1-methycycloheene!

(plain.Answer:

Addition to methylenecycloheane is more hihly reioselecti3e. There is a reater difference in the acti3ationeneries leadin to a primary and tertiary carbocation than in the acti3ation eneries leadin to a secondary and

tertiary carbocation.Type: SA

Section: 0-0

1)

=ro3ide the maRor oranic products) in the reaction below.

Answer:

Type: SA

Section: 0-0


135/159

19)

What is the maRor product of the followin reaction!

A)

8$)

88%)

888')

8V()

V

Answer:

%Type: *%Section: 0-"

2)

What is the maRor product from the acid-catalyBed hydration of 2-methyl-2-pentene!

A)


136/159

2-methylpentane

$)

2-methyl-1-pentanol

%)

2-methyl-2-pentanol

')

2-methyl-+-pentanol

()

1-methoypentaneAnswer:

%

Type: *%Section: 0-"

21)

Which of the followin alenes would ha3e the smaller heat of hydroenation! (plain.

%,2%,2 or %,+%,%,2Answer:

%,+%,%,2would ha3e the smaller heat of hydroenation because the double bond is more stable than that of

The reater stability is due to the fact that the double bond in propane is more alyl substituted than that

of ethene. Type: SASection: 0-"


137/159

22)


Answer:

Type: SASection: 0-"

2+)


Answer:

Type: SA

Section: 0-"

20)


Answer:

Type: SA

Section: 0-"


138/159


139/159

2")


Answer:

Type: SA

Section: 0-"

2/)

=ro3ide the structure of the maRor oranic product of the followin reaction.

Answer:

Type: SA

Section: 0-"

24)


Answer:


140/159

Type: SA

Section: 0-"


141/159

2)


Answer:

Type: SA

Section: 0-"

29)

Which of the followin alenes yields) +-bromo-+-methylpentane as the maRor product upon addition of ,$r!

A)

8 and 88 only

$)

888 only

%)

85 885 nad 888 only

')

all of them

()

none of them

Answer:

'Type: *%Section: 0-" and 0-/

+)


142/159

Which of the followin carbocations is liely to rearrane!

A)

8$)

88%)

888

')

8V()

88 and 8V

Answer:

(Type: *%

Section: 0-/


143/159

+1)

What is the name of the maRor oranic product of the followin reaction!

A)

+5+-dimethyl-1-butanol$)

+5+-dimethyl-2-butanol%)

25+-dimethyl-2-butanol')

25+-dimethyl-1-butanol()

0-methyl-2-pentanol

Answer:

%Type: *%

Section: 0-/

+2)


Answer:



144/159

++)

What is the maRor product of the followin reaction!

A)

8$)

88 %)

888')

8V()

V

Answer:



145/159

+0)

Which reaction intermediate is formed when $r2Q%%l0reacts with cycloheene!

A)

8

$)

88

%)

888

')

8V

()

V

Answer:

'Type: *%

Section: 0-4

+")


Answer:


146/159

Type: SA

Section: 0-4

+/)


Answer:

Type: SA

Section: 0-4


147/159

+4)


Answer:

Type: SA

Section: 0-4

+)

=ro3ide a detailed5 step-by-step mechanism for the reaction shown below.

Answer:

Type: SA

Section: 0-4

+9)

'raw the structure of the maRor product of the reaction below.

Answer:


148/159

Type: SA

Section: 0-4


149/159

0)


Answer:

Type: SA

Section: 0-4

01)


Answer:

Type: SA

Section: 0-4

02)

Which of the followin is the best reaction se>uence to use if one wants to accomplish a *aro3nio3 addition of

water to an alene with minimal seletal rearranement!A)

water 7 dilute acid

$)

water 7 concentrated acid


150/159

%)

oymercuration-demercuration')

hydroboration-oidation

()

none of the abo3e

Answer:

%Type: *%

Section: 0-

0+)


Answer:

Type: SA

Section: 0-

00)


Answer:

Type: SA

Section: 0-


151/159

0")


Answer:

Type: SA

Section: 0-

0/)


Answer:

Type: SA

Section: 0-


152/159

04)


Answer:

Type: SA

Section: 0-

0)


Answer:

Type: SASection: 0-

09)

What reaents are needed to accomplish the followin transformation!

A)


153/159

,2Q,7

$)

,2Q=eroide

%)

,-

')

$,+

()

1. $,+Q 2. ,-5 ,225 ,2

Answer:

(Type: *%

Section: 0-1


154/159

")

What reaents can best be used to accomplish the followin transformation!

A)

1. $,+IT,# 2. ,-5 ,22

$)

,75 ,2

%)

1. ,Ac)25 ,2QT,# 2. &a$,0')

1. ,2%%#+)25 %,+, 2. &a$,0()

&a,5 ,2

Answer:

AType: *%

Section: 0-1

"1)


Answer:


155/159


"2)


Answer:

Type: SA

Section: 0-1


156/159

"+)


Answer:

Type: SA

Section: 0-1

"0)

Which of the followin reaents i3es the reaction shown below!

%,+%, %,27 ! %,+%,2%,+

A)

,2Q,%l

$)

,2Q,2S0

%)

,2Q&i

')

,2Q&i

()

,2Q,2S0

Answer:

%Type: *%

Section: 0-11


157/159

"")

Which of the followin is the most stable alene!

A)

$)

%)

')

()

Answer:

(Type: *%

Section: 0-11

"/)

;pon hydroenation5 which of the followin alenes releases the least heat per mole!

A)


158/159

+50-dimethyl-1-heene

$)

Z)-+50-dimethyl-2-heene

%)

E)-+50-dimethyl-2-heene

')

Z)-+50-dimethyl-+-heene

()

E)-+50-dimethyl-+-heeneAnswer:

(


"4)


Answer:

Type: SA

Section: 0-11

")

%omplete the followin tree of reactions by i3in the maRor products:


159/159

Answer:

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Organic Chemistry Practice Test