FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry & Biochemistry

CHM 2210-U02 – ORGANIC CHEMISTRY I

Fall 2012

PRACTICE EXAM I

CHM 2210-U02, Fall 2012 Practice Exam I, Page 2

FLORIDA INTERNATIONAL UNIVERSITY

Department of Chemistry

Dr. Keller PRACTICE EXAM I CHM 2210-U02 Fall 2012 MULTIPLE CHOICE QUESTIONS: Answer each of the following questions by bubbling in the correct response on the Scantron answer sheet.

1. Which of the following is the Lewis structure for

CH3CH2O2H?

H C

H

H

C

H

H

O O H

: :::

H C

H

H

O C

H

O H: ::

H C

H

H

C

H

O

O H

H

:

::

:

H C

H

H

O C O H

H

H

::

::

H C

H

H

C

H

H

C O H

O

::

a.

b.

c.

d.

e.

: :

2. How many ester functional groups are in the

potent anticancer compound Taxol?

NH

O

O

OH

O

O

O

O

OH

OOO

OTaxol

a. 0 b. 2 c. 3 d. 4 e. 5

3. Which one of the following structures is not

identical to the others?

CH3CH2CHCH3

CH2

CH3CH2

CH3CH2

CCH3

H

CH2

CH2CH3

CH3CH2

CCH3

H

CH

CH3

CH3

CH3CH2CH2

CH CH3

CH2CH3

a.

b.

c.

d.

e.

4. Which of the following cannot be a correct Lewis structure?

H B H

H

: ::

F C F

F

: :

:

F

: ::

:

::

:

: :

: :

::

:O :: N:: O:

H

:

: :

:

H:C::C:H

:

:

H

All are correct

a.

b.

c.

d.

e.

CHM 2210-U02, Fall 2012 Practice Exam I, Page 3 5. Which of the following represent proper

resonance structures for CH2N2?

H:C:N:::N:

:

H

H:C::N::N:

:

H

:

H:C::N:N:

: ::

H

H:C::N::N:H

: :

H

e. both a and b are correct.

a.

b.

c.

d.

:

6. Which of the following structures must be

incorrect?

OH

C

OH

O

ClCH3

C

a.

b.

c.

d.

e.

7. Which of the following molecules contain both

an alcohol and an aldehyde functional group?

O

O

H

OH

O

O

HONH2

OOH

O

HN

CO2H

O

a.

b.

c.

d.

e.

8. Guanacastepene is a natural product that was recently isolated and shown to be a potent antibiotic. How many different functional groups does this structure possess?

HO

OO

CH3CH3

O

OO

Guanacastepene

a. 1 b. 2 c. 3 d. 4 e. 5 9. Which compound is not a constitutional isomer

of the others?

N O

O

N

HN

N

O

O

a.

b.

c.

d.

e. All of the above are constitutional

isomers of each other. 10. The formal charge on sulfur in sulfuric acid is:

S OH

O

HO

O

::

::

: :

: :

a. 0 b. -1 c. +1 d. -2 e. +2

CHM 2210-U02, Fall 2012 Practice Exam I, Page 4 11. What is the molecular formula of limonene, the

major volatile compound in orange peel oil?

Limonene

a. C10H18 b. C10H20 c. C10H16 d. C11H14 e. C11H18

12. Expansion of the valence shell to accommodate more than 8 electrons is possible with:

a. Fluorine b. Nitrogen c. Carbon d. Sulfur e. Beryllium

13. Which of the following is an ion with a net “-1”

charge?

O CH3 O N O O N

O

O

::

::

::

::

::

::

: :

:

:

a. b. c.

d. Two of these

e. All of these 14. Which of the following structures is not a

resonance form of the following species?

O

OO

O

O

:

::

:

:

:

:

:

a.

b.

c.

d.

e. They are all resonance structures.

:

15. What would be the bond-line form of the

following condensed structure?

CH3CH2CH(CN)CH=CH2

N

HN

N

N

N

a.

b.

c.

d.

e.

16. Which of the following is not a resonance structure of the others?

OCH3

H

H

OCH3

H

H

OCH3

H

H

OCH3

H

H

OCH3

H

H

::

::

:

::

::

a.

b.

c.

d.

e.

CHM 2210-U02, Fall 2012 Practice Exam I, Page 5 17. In which structure(s) below does the oxygen have

a formal charge of +1?

H O

H

HH O

H C

H

O H

CH3 O

CH3

CH3

I II

III IV

a. I only d. I and IV b. II only e. I, III, and IV c. I and III 18. What is the correct line-bond representation for

the following condensed structural formula?

a.

b.

c.

d.

e. None of these is correct.

CH3CH2CH(CH3)CH2C(CH3)2CH(CH2CH3)CH(CH3)2

19. Which is an acceptable Lewis structure for methyl

azide?

H C

H

H

N N N: H C

H

H

N N N:

H C

H

H

N N N:H C

H

H

N N N:

: :

:::

a.

b.

c.

d.

1. The following electron configuration represents _______

1s

sp3 sp3 sp3 sp3

a. the ground state of boron.

b. the sp3 hybridized state of carbon.

c. the sp3 hybridized state of nitrogen.

d. the bonding molecular orbital of carbon.

e. the antibonding molecular orbital of carbon.

2. Which is the strongest acid?

CH2CH2CH2CH2CH2CO2H

CH3CHCH2CH2CH2CO2H

Cl

Br

CH3CH2CH2CCH2CO2H

Br

Br

CH3CH2CH2CHCH2CO2H

F

CH3CH2CH2CCH2CO2H

F

F

a.

b.

e.

c.

d.

3. The process of adding electrons one by one to atomic orbitals beginning with the lowest energy is described by:

a. the Aufbau Principle

b. Hund’s Rule

c. the de Broglie Relation

d. the Pauli Exclusion Principle

e. Coulomb’s Law

4. In the following molecule, how many carbon atoms are in the sp3 hybridization state?

O

OCH3

a. 2 b. 4 c. 5 d. 6 e. 11

5. What would be the expected value of the indicated bond angle?

Br

a. 120˚ b. 90˚ c. 104˚ d. 180˚ e. 109.5˚

24.

23.

22.

21.

20.

6. Which of the following statements is(are) true of

sp orbitals? a. Orbitals of the sp type have 50% s-character

and 50% p-character. b. They are hybrid orbitals. c. They are linear with respect to each other. d. They result when one s-orbital and one

p-orbital are mixed. e. All are correct. 7. What is the hybridization of the each of the

labeled atoms for the potent neurotoxin Gephyrotoxin?

N

H

H

H

H

OH

A

B

C

D

E

Gephyrotoxin

a. A = sp2, B = sp, C = sp2, D = sp3, E = sp3

b. A = sp2, B = sp, C = sp3, D = sp3, E = sp2

c. A = sp2, B = sp, C = sp2, D = sp3, E = sp2

d. A = sp2, B = sp, C = sp3, D = sp3, E = sp3

e. A = sp, B = sp, C = sp3, D = sp3, E = sp3 8. Which of the following is not considered a

Lewis acid?

H

CH3OH2

AlCl3

CH3 C

CH3

CH3BF3

a.

b.

c.

d.

e.

11. Arrange these acids in the order of increasing

acidity

SiH4 H2S HCl PH3

a. SiH4, H2S, HCl, PH3

b. HCl, H2S, SiH4, PH3

c. HCl, H2S, PH3, SiH4

d. SiH4, PH3, H2S, HCl

e. PH3, SiH4, H2S, HCl

12. Expansion of the valence shell to

accommodate more than 8 electrons is possible with:

a. Fluorine b. Nitrogen

c. Carbon d. Sulfur e. Beryllium

29.

28.

27.

26.

25.

13. Does the equilibrium of this reaction lie to the

right or to the left?

ClCH2CH2OH + CH3CHO

Cl

:

::

:: ClCH2CH2O + CH3CHOH

Cl

:

::

::

a. To the right

b. To the left

c. It cannot be determined without pKa data.

14. Which molecular shape is not represented in the following group of molecules?

CH3 S

O

CH3:

: :

O N

O

O

:: :

:

: :

: : Cl P

Cl

Cl

: :

::

:: : :

:

:O S O S C S

:

::: : :: :

:

a. linear

b. bent

c. pyramidal

d. trigonal planar

e. tetrahedral

15. Identify the atomic orbitals which are

overlapping to form the C-2---C-3 sigma bond (indicated by the arrow) in the following molecule:

1

2

3

4

5

6

7

a. sp2,sp2 c. sp2,sp3 b. sp2,sp d. sp3,sp2 e. sp,sp2

16. Consider the following 4 alkenes:

CH3CH2CH2CH=CHCH2CH3

CH3CH2CH2CH2CH2CH2CH=CH2

CH3CH2CH=C(Cl)CH2CH2CH3

CH3C=CHCH2CH2CH2CH2CH3

CH3

I

II

III

IV

Which structures can exist as cis/trans isomers? a. I and II c. I and IV b. I and III d. II and III e. I, III, and IV

17. The conjugate base of sulfuric acid is:

a. H3SO4

+ c. HSO4

-

b. SO4

-2 d. H2SO3

e. HSO3

-

18. What is the spatial arrangement of the methyl

anion ( :CH3 )?

a. Octahedral c. Trigonal planar b. Tetrahedral d. Linear e. Pyramidal 19. Which of the following is not a Bronsted-

Lowry acid?

a. H2O c. +NH4

b. (CH3)3N d. CH3CO2H e. HC CH

36.

35.

34.

33.

32.

31.

30.

20. Which pair of species are both bases in the

following reaction:

HCN + H2O CN + H3O

a. H2O and CN

b. H3O and H2O

c. HCN and H3O

d. HCN and CN

e. H3O and CN 21. Which of these is not a Lewis acid? a. AlBr3 c. Ph3P

b. BCl3 d. H+

e. All are Lewis acids

22 Which of these is not a true statement? a. All Lewis bases are also Bronsted-Lowry

bases. b. All Lewis acids contain hydrogen. c. All Bronsted-Lowry acids contain

hydrogen. d. All Lewis acids are electron-deficient. e. According to Bronsted-Lowry theory,

ammonia is both an acid and a base. 23. Which acid/base reaction would not take

place in the direction written?

CH3CH2Li + CH3CH2OH CH3CH3 + CH3CH2OLia.

CH3CO2H + CH3CH2ONa CH3CO2Na + CH3CH2OH

b. HC CH + NaOH HC CNa + H2O

e.

c.HC CNa + H2O HC CH + NaOH

d. CH3CH2OH + NaH CH3CH2ONa + H2

25. Which base would completely remove a

proton from phenol (C6H5OH)?

a. NaCl b. H2O c. CH3CO2

- Na

+

d. CH3CH2O- K

+ e. All of the above.

26. Which one of the following is a true

statement? a. The stronger the acid, the larger is its pKa.

b. The conjugate base of a strong acid is a strong base.

c. Acid-base reactions always favor the formation of the stronger acid and the stronger base.

d. Strong acids can have negative pKa values.

e. Hydrogen need not be present in the molecular formula of a Bronsted-Lowry acid.

37.

38.

39.

40.

41.

42.

27. Which anion is the strongest base?

CH3 C

O

Oa.

b. CH3CH2

c. Cl

d. CH3CH2O 28. When acid-base reactions reach equilibrium,

there have been formed:

a. the weaker acid and the weaker base. b. The weaker acid and the stronger base. c. The stronger acid and the weaker base. d. All acid-base reactions go to completion; they

are not equilibrium processes.

43.

44.