Chap deuce deuce

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1

Which of the following compounds will not undergo reaction with an enolate?

A) 1-pentene
B) bromine
C) Propanal
D) 1-bromobutane
E) benzoyl chloride

A) 1-pentene

2

The relationship between ketones and their corresponding enols is one of:

A) allotropes
B) tautomers
C) enantiomers
D) diastereomers
E) cis-trans isomers

B) tautomers

3

Which of the following reagents will quanititatively convert an enolizable ketone to its enolate salt?

A) lithium hydroxide
B) lithium diisopropylamide
C) methyllithium
D) diethyllithium
E) pyridine

B) lithium diisopropylamide

4

The reaction of LDA with acetophenone produce:

A) an enol
B) an enolate
C) an ylide
D) alkylation
E) halogenation

B) an enolate

5

Disregarding stereoisomers, how many different enols can phenylacetone form?

A) 0
B) 1
C) 2
D) 3
E) 4

C) 2

6

Disregarding stereoisomers, how many different enols can the beta-diketone Ch3CoCh2CoCh2Ch3 form?

A) 0
B) 1
C) 2
D) 3
E) 4

E) 4

7

What type of product results when 3-pentanone is treated with LDA at low temperature?

A) enolate
B) enol
C) amide
D) imine
E) enamine

A) enolate

8

When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound?

A) 0
B) 1
C) 2
D) 3.
E) 4

D) 3

9

When ketone and its enol are in equilibrium, under most conditions the concentration of the enol is _____ the concentration of the ketones

A) slightly higher than
B) equal to
C) much higher than
D) much lower than
E) exactly half of

D) much lower than

10

(S)-2-methylbutanal _____ upon sitting in the acidic or a basic aquoes solution

A) racemizes
B) esterifies
C) inverts completely to the R config
D) hydrolyzes
E) irreversibly forms the hydrate

A) racemizes

11

Which of the following will alkylate a lithium enolate most rapidly?

A) methyl bromide
B) isopropyl bromide
C) neopentyl bromide
D) bromobenzene
E) 2-methylbromobenzene

A) methyl bromide

12

Methylamine reacts with acetophenone to yield the:

A) iminium salt
B) imine
C) acetal
D) amide
E) enamine

B) imine

13

Which of the following will react most slowly with an enamine?

A) isopropyl chloride
B) methyl bromide
C) acetyl chloride
D) benzyl chloride
E) allyl bromide

A) isopropyl chloride

14

What type of product results when 3-pentanone reacts with dimethylamine?

A) enolate
B) enol
C) amide
D) imine
E) enamine

E) enamine

15

Which of the following ketones will give a positive iodoform test?

A) 4-heptanone
B) 3-hexanone
C) 2-hexanone
D) cyclohexanone
E) 2-methyl-3-pentanone

C) 2-hexanone

16

The alpha-halogenation of cyclohexanone:

A) is catalyzed by base
B) is slowed by the presence of acid
C) requires one equivalent of base
D) requires one equivalent of acid
E) is catalyzed by the sodium halide salt

C) requires one equivalent of base

17

What is the carbon nucleophile which attacks molecular bromine in the acid-catalyzed alpha-bromination of a ketone?

A) an enolate
B) a grignard reagent
C) an acetlyide
D) a carbocation
E) an enol

E) an enol

18

When aldehydes are subjected to the same conditions that alpha-halogenate ketones, they are:

A) alpha-halogenated as well
B) reduced to alcohols
C) converted to the acid halide
D) oxidized to the acid or carboxylate
E) esterified

D)oxidized to the acid or carboxylate

19

In the iodoform reaction, a mehtyl ketone is converted to the ____ upon treatment with excess iodine and hydroxide.

A) carboxylate
B) acyl iodide
C) primary alkyl iodide
D) aldehyde
E) primary amide

A) carboxylate

20

What reagents are needed to complete the following synthesis?

A) 1) Naoh/heat 2) HCL
B) NaOH/ I2 2) HCL
C) warm conc, KMnO4/ Naoh 2) HCL
D) Ag(Nh3)2OH 2) HCL

B) NaOH/ I2 2) HCL

21

The Hell-Volhard-Zelinsky reaction involves:

A) the alpha-bromination of carboxylic acids
B) the alpha bromination of ketones
C) the bromination of alcohols
D) the oxidation of aldehydes to acids
E) none of the above

A) the alpha-bromination of carboxylic acids

22

An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this?

A) a Fischer esterification
B) an acid-catalyzed aldol condensation
C) a base-mediated aldol condensation
D) a Hell-Volhard-Zelinsky reaction
E) a Selman-jones reaction

C) a base-mediated aldol condensation

23

The aldol condensation is:

A) an irreversible reaction
B) an equilibrium reaction
C) a tautomerization
D) an isomerization
E) a type of esterification

B) an equilibrium reaction

24

Which of the following is another name for the product of an aldol condensation?

A) beta-hydroxyaldehyde
B) alpha-hydroxyaldehyde
C) acetal
D) beta-ketoester
E) 1,3-dialdehyde

A) beta-hydroxyaldehyde

25

Which of the following could result from the dehydration of a self-aldol condensation?

A) 4-methyl-3-penten-2-one
B) 4-methyl-4-penten-2-one
C) 4-methyl-5-hexen-2-one
D) 4-methyl-4-hexen-2-one
E) 3-methyl-4-penten-2-one

A) 4-methyl-3-penten-2-one

26

What product results when an aldol is dehydrated?

A) conjugated alkyne
B) beta-diketone
C) beta-ketoester
D) alpha, beta - unsaturated aldehyde
E) beta,gamma- unsaturated aldehyde

D) alpha, beta - unsaturated aldehyde

27

In theory a poorly planned crossed aldol reaction can produce how many different aldol regioisomers?

A) 1
B) 2
C) 3
D) 4
E) 5

D) 4

28
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Predict the Pka unit of the indicated proton within the plus/minus 1 pka unit?

A) 5
B) 11
C) 19
D) 24

D) 24

29

Which of the following is least likely to undergo a smooth crossed Claisen condensation with methyl pentanoate??

A) (Ch3)3CCO2Ch3
B) PhCH2CO2Ch3
C) PhCo2Ch3
D) HCo2Ch3

B) PhCH2CO2Ch3

30

Which of the following is most acidic?

A) acetone
B) ethyl acetate
C) malonic ester
D) acetoacetic ester
E) acetaldehyde

D) acetoacetic ester

31

What is the approximate pKA of acetone?

A) 45
B) 20
C) 13
D) 10
E) 4

B) 20

32

What is the approximate pKa of diethyl malonate?

A) 45
B) 20
C) 13
D) 10
E) 4

C) 13

33
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Which of the following structures could be constructed by way of a malonate ester alkylation?

A) 1 only
B) 3 only
C) 3 and 4
D) 1 and 3

C) 3 and 4

34

In the Michael reaction, addition to the alpha,beta-unsaturated carbonyl occurs in a:

A) 1,2-fashion
B) 1,3-fashion
C) 1,4-fashion
D) 1,5-fashion
E) Diels-Alder reaction

C) 1,4-fashion

35

Which of the following is a nucleophile that does conjugate additions?

A) Ch2-ChChO
B) Ch2-ChCn
C) Ch2-ChCo2Ch3
D) Ch3Ch2MgBr
E) (Ch3)2CuLi

E) (Ch3)2CuLi

36
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Which of the following is the best Michael acceptor??

D

37
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The following compound was found to inhibit HIV -1(J. Med.Chem. 2013, 1812). Predict the structure of the hydrolysis product.

card image

B

38
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What reagents are needed to complete the following synthesis?

A) 1)NaOH/heat, 2) HCl (aq)
B) 1) NaOH/I2, 2) HCl (aq)
C) 1) warm conc. KMnO4/ NaOh, 2) HCl (aq)
D) 1) AG(NH3)2OH, 2) HCl (aq)

B) 1) NaOH/I2, 2) HCl (aq)

39
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A) greater than 1
B) less than 1

A) greater than 1

40
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A) greater than 1
B) less than 1

B) less than 1

41
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A) greater than 1
B) less than 1

A) greater than 1

42
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Rank the following compounds in order of decreasing acidity

A) A>D>B>C
B) B>C>A>D
C) D>A>C>B
D) C>B>D>A

A) A>D>B>C

43
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Which is an aldol condensation product derived from the self-condensation of 2-butanone?

A) A
B) B
C) C
D) D

C) C

44
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Which set of conditions will perform the following transformation?

A) HBr, H2O2
B) Br2, NaOH
C) a. Br2/PBr3 b. H2O
D) NBS, light

C) a. Br2/PBr3 b. H2O

45
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What is the product of the following reaction?

A) A
B) B
C) C
D) D

C) C

46
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What is the product of the following reaction?

A) A
B) B
C) C
D) D

C) C