1 A Uhcl Orgo Ii Exam3.0 Questions Ch22

Front 1

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

Back 1

A) 1-pentene

Front 2

2) The relationship between ketones and their corresponding enols is one of:
A) allotropes.
B) tautomers.
C) enantiomers
D) diastereomers.
E) cis-trans isomers.

Back 2

B) tautomers.

Front 3

3) Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?
A) lithium hydroxide
B) lithium diisopropylamide
C) methyllithium
D) diethylamine
E) pyridine

Back 3

B) lithium diisopropylamide

Front 4

4) The reaction of LDA with acetophenone produces:
A) an enol.
B) an enolate.
C) an ylide.
D) alkylation.
E) halogenation.

Back 4

B) an enolate.

Front 5

5) When a ketone and its enol are in equilibrium, under most conditions the concentration of the enol is __________ the concentration of the ketone.
A) slightly higher than
B) equal to
C) much higher than
D) much lower than

Back 5

D) much lower than

Front 6

E) exactly half of
6) Disregarding stereoisomers, how many different enols can phenylacetone form?
A) 0
B) 1
C) 2
D) 3
E) 4

Back 6

C) 2

Front 7

7) Disregarding stereoisomers, how many different enols can the β-diketone CH3COCH2COCH2CH3 form?
A) 0
B) 1
C) 2
D) 3
E) 4

Back 7

E) 4

Front 8

8) What type of product results when 3-pentanone is treated with LDA (lithium diisopropylamide) at low temperature?
A) enolate
B) enol
C) amide
D) imine
E) enamine

Back 8

A) enolate

Front 9

9) 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) 5

Back 9

D) 3

Front 10

10) (S)-2-Methylbutanal __________ upon sitting in an acidic or a basic aqueous solution.
A) racemizes
B) esterifies
C) inverts completely to the R configuration
D) hydrolyzes
E) irreversibly forms the hydrate

Back 10

A) racemizes

Front 11

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

Back 11

A) methyl bromide

Front 12

12) Methylamine reacts with acetophenone to yield the:
A) iminium salt.
B) imine.
C) acetal.
D) amide
E) enamine.

Back 12

B) imine.

Front 13

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

Back 13

A) isopropyl chloride

Front 14

14) What type of product results when 3-pentanone reacts with dimethylamine?
A) enolate
B) enol
C) amide
D) imine
E) enamine

Back 14

E) enamine

Front 15

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

Back 15

C) 2-hexanone

Front 16

16) The α-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.

Back 16

C) requires one equivalent of base.

Front 17

17) What is the carbon nucleophile which attacks molecular bromine in the acid-catalyzed α-bromination of a ketone?
A) an enolate
B) a Grignard reagent
C) an acetylide
D) a carbocation
E) an enol

Back 17

E) an enol

Front 18

18) When aldehydes are subjected to the same conditions that α-halogenate ketones (i.e., X2 and aqueous acid or base), they are:
A) α-halogenated as well.
B) reduced to alcohols.
C) converted to the acid halide.
D) oxidized to the acid or carboxylate.
E) esterified.

Back 18

D) oxidized to the acid or carboxylate.

Front 19

19) In the iodoform reaction, a methyl 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

Back 19

A) carboxylate

Front 20

21) The Hell-Volhard-Zelinsky reaction involves:
A) the α-bromination of carboxylic acids.
B) the α-bromination of ketones.
C) the bromination of alcohols.
D) the oxidation of aldehydes to acids.
E) none of the above.

Back 20

A) the α-bromination of carboxylic acids.

Front 21

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

Back 21

C) a base-mediated aldol condensation

Front 22

23) The aldol condensation is:
A) an irreversible reaction.
B) an equilibrium reaction.
C) a tautomerization.
D) an isomerization.
E) a type of esterification.

Back 22

B) an equilibrium reaction.

Front 23

24) Which of the following is another name for the product of an aldol condensation
A) β-hydroxyaldehyde
B) α-hydroxyaldehyde
C) acetal
D) β-ketoester
E) 1,3-dialdehyde

Back 23

A) β-hydroxyaldehyde

Front 24

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

Back 24

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

Front 25

26) What product results when an aldol is dehydrated?
A) conjugated alkyne
B) β-diketone
C) β-ketoester
D) α,β-unsaturated aldehyde
E) β,γ-unsaturated aldehyde

Back 25

D) α,β-unsaturated aldehyde

Front 26

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

Back 26

D) 4

Front 27

28) 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
E) (CH3O)2CO

Back 27

B) PhCH2CO2CH3

Front 28

29) Which of the following is most acidic?
A) acetone
B) ethyl acetate
C) malonic ester
D) acetoacetic ester
E) acetaldehyde

Back 28

D) acetoacetic ester

Front 29

30) What is the approximate pKa of acetone?
A) 45
B) 20
C) 13
D) 10
E) 4

Back 29

B) 20

Front 30

31) What is the approximate pKa of diethyl malonate?
A) 45
B) 20
C) 13
D) 10
E) 4

Back 30

C) 13

Front 31

32) Arrange the following compounds in order of increasing acidity:
acetone, ethyl acetoacetate, ethyl acetate, and ethanol.
A) acetone < ethyl acetate < ethanol < ethyl acetoacetate
B) acetone < ethanol < ethyl acetate < ethyl acetoacetate
C) ethyl acetate < ethanol < acetone < ethyl acetoacetate
D) ethyl acetate < acetone < ethanol < ethyl acetoacetate

Back 31

D) ethyl acetate < acetone < ethanol < ethyl acetoacetate

Front 32

34) In the Michael reaction, addition to the α,β-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.

Back 32

C) 1,4-fashion.

Front 33

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

Back 33

E) (CH3)2CuLi

Front 34

20) Which set of reagents would best accomplish the following transformation?
A) Br2 / HBr
B) Br2 / PBr3
C) Br2 / NaOH
D) PBr3

Back 34

A) Br2 / HBr

Front 35

33) Which of the following structures could be constructed by way of a malonate ester alkylation?
A) 1 only
B) 3 only
C) 3 & 4
D) 1 & 3

Back 35

C) 3 & 4

Front 36

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

Back 36

D)