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1. Which of the following is 3-ethyl-2-hexanone?

a. A

b. B

c. C

*d. D

2. What is the hybridiation of the carbon ato! in a carbonyl gro"#?

a. 2#

b. s#

*c. s#2

d. s#3

3. Which of the following is an acce#table na!e for the co!#o"nd shown

below?

*a. ortho-!ethoxybenaldehyde

b. ortho-!ethoxyaceto#henone

c. ortho-for!ylanisole

d. ortho-!ethylaceto#henone

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$. What is the na!e of the following co!#o"nd?

a. 3-tert-b"tylhe#tanal

b. 2-iso#ro#ylhe#tanal

*c. 3-iso#ro#ylhe#tanal

d. 3-b"tyl-$-!ethyl#entanal

%. Which of the following is a he!iacetal?

a. A

*b. B

c. C

d. D

&. Which of the following is an acetal?

a. A

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b. B

c. C

*d. D

'. What is the ()AC na!e of the following co!#o"nd?

a. 3-!ethyl-%-he#tanone

b. %-ethyl-3-hexanone

*c. %-!ethyl-3-he#tanone

d. 2-ethyl-$-hexanone

+. (dentify the correct ()AC na!e of the co!#o"nd below.

a. $-benyl-%-!ethylhexanal

b. %-iso#ro#yl-%-#henylb"tanal

c. 2-!ethyl-3-#henylhexanal

*d. %-!ethyl-$-#henylhexanal

,. Which of the following is an acce#table ()AC na!e for the co!#o"nd

below?

a. o-bro!o-m-chlorobenaldehyde

b. &-bro!o-3-chlorobenaldehyde

*c. 2-bro!o-%-chlorobenaldehyde

d. 1-bro!o-$-chlorobenaldehyde

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1. Which of the following has the largest e/for the for!ation of the

hydrate 0as shown below?

a. A

b. B

c. C

*d. D

11. he carbon-oxygen bond of an aldehyde is for!ed by o4erla# of

which two orbitals?

a. s#-s#

b. s#2-s#2

c. s#2-2#

*d. 2#-2#

12. Which of the reagents below will oxidie a secondary alcohol to a

5etone?

a. 6iAl7$

b. 7(8$

*c. 2Cr28'9 72:8$;728

d. 7g:8

$

9 7

2

:8

$

;7

2

8

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13. (dentify the reagents needed to carry o"t the following con4ersion.

a. 72;6indlar d followed by 72:8$;728

b. 83followed by 728

*c. 7289 7g:8$;72:8$

d. 6iA17$followed by 728

1$. Which one of the following wor5s best as the reaction ste#s to

carry o"t the con4ersion below?

a. A

*b. B

c. C

d. D

1%. Which of the following reagents wo"ld carry o"t the isoto#ic

s"bstit"tion reaction shown below?

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a. 1+82;

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b. B

c. C

d. D

1+. he co!#o"nd shown below is the he!iacetal for!ed between

*a. #ro#anal and 2-#ro#anol.

b. 2-!ethyl#ro#anal and ethanol.

c. acetone and 1-#ro#anol.

d. ethanal and 2-!ethyl-1-#ro#anol.

1,. What is the #rod"ct of the reaction of b"tanal with excess !ethanol

and catalytic s"lf"ric acid?

a. A

b. B

c. C

*d. D

2. (dentify the #rod"cts of the hydrolysis of the following co!#o"nd.

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*a. A

b. B

c. C

d. D

21. Which one of the following is not an inter!ediate in the acid-

catalyed reaction of benaldehyde with 2 e/"i4alents of !ethanol to

gi4e benaldehyde di!ethyl acetal?

a. (

*b. ((

c. (((

d. (=

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22. he co!#o"nd shown below is the cyclic he!iacetal of

a. %-hydroxyhe#tanal.

*b. %-hydroxy-2-he#tanone.

c. &-hydroxy-3-he#tanone.

d. &-hydroxyhe#tanal.

23. What is the #rod"ct of the reaction shown?

*a. A

b. B

c. C

d. D

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2$. Acid-catalyed hydrolysis of the cyclic acetal below gi4es

a. ethanal and 2-chlorocyclohexanol.

b. 192-ethanediol and 2-chlorocyclohexanol.

c. ethanol and 2-chlorocyclohexanol.

*d. 192-ethanediol and 2-chlorocyclohexanone.

2%. What are the #rod"cts of the following reaction?

a. cyclohexanone and ethanol

b. cyclohexanone and ethanal

*c. 192-cyclohexanediol and ethanal

d. 192-cyclohexanediol and ethanol

2&. he acid-catalyed reaction of #ro#anal with 2 e/"i4alents of

!ethanol for!s an acetal. his can !echanistically be tho"ght of as

*a. an addition reaction followed by a s"bstit"tion reaction.

b. a s"bstit"tion reaction followed by an addition reaction.

c. an eli!ination reaction followed by a s"bstit"tion reaction.

d. an addition reaction followed by an eli!ination reaction.

2'. Which one of the following gi4es ethanal9 C73C7>89 0as one of two

#rod"cts when added to an a/"eo"s sol"tion of 7Cl?

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a. A

b. B

*c. C

d. D

2+. Which synthetic !ethod below correctly does the following

con4ersion?

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a. A

b. B

*c. C

d. D

2,. What is the #rod"ct of the reaction below?

*a. 2-!ethyl-1-#entene

b. 2-!ethyl-2-#ro#yloxirane

c. $-!ethyl-1-#entene

d. 1-#entene

3. Do!iodol9 shown below9 is "sed !edicinally as a !"colytic agent.

What are the acid-catalyed hydrolysis #rod"cts of Do!iodol?

*a. A

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b. B

c. C

d. D

31. Which of the following reacts with 0C73C722

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a. A

b. B

c. C

*d. D

33. Baeyer-=illiger oxidation reactions can "se #eroxycarboxylic acids

to con4ert 5etones to

a. carboxylic acids.

*b. esters.

c. e#oxides.

d. -hydroxy 5etones.

3$. (dentify the !issing reagent for the reaction below.

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*a. A

b. B

c. C

d. D

3%. What is the #rod"ct of the following Baeyer-=illiger oxidation

reaction?

a. A

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*b. B

c. C

d. D

3&. Which of the following is the #rod"ct of the reaction between

acetone9 C73C8C739 and !ethyla!ine9 C73

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3,. Which of the following !ethods can be "sed to synthesie 2-!ethyl-

1-hexene9 shown below9 with no for!ation of iso!eric by-#rod"cts?

a. A

b. B

c. C

*d. D

$. Which of the following is the best !ethod to synthesie 2-!ethyl-2-

#entene9 shown below9 with little or no by-#rod"ct for!ation?

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a. A

b. B

*c. C

d. D

$1. What is the #rod"ct of the reaction se/"ence below?

a. 2-!ethyl-1-hexene

b. 293-di!ethyl-2-#entene

c. 2-!ethyl-2-hexene

*d. 3-!ethyl-1-hexene

$2. What is the #rod"ct of the reaction shown below?

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a. A

b. B

c. C

*d. D

$3. What #rod"ct wo"ld be ex#ected in this reaction?

a. A

b. B

c. C

*d. D

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$$. (n what !a@or for! wo"ld this diol-aldehyde exist?

a. A

b. B

*c. Cd. D

$%. (n a/"eo"s acid9 only 1' of the aldehyde at right is #resent as

shown9 along with 2 of the enol. What s#ecies acco"nts for +1 of the

!aterial?

a. the enol

b. the enolate

c. the aldehyde

*d. the hydrate

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$&. rior to 1,%9 !any h"ndreds of 5etones were reacted with 29$-

dinitro#henylhydraine and hydroxyla!ine beca"se

a. it hel#ed get the 5etones #"re

b. it !ade

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$,. At abo"t what ( fre/"ency is the C>8 gro"# ty#ically fo"nd?

a. 1&$ c!-1

*b. 1'2 c!-1

c. 22$ c!-1

d. 3$ c!-1