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ochem ch. 22 wade

question

3) 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
answer

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

B
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5) 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
answer

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

B
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10) Disregarding stereoisomers, how many different enols can phenylacetone form? A) 0 B) 1 C) 2 D) 3 E) 4
answer

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

E
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12) 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
answer

A
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13) 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
answer

D
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22) 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 E) exactly half of
answer

D
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23) (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
answer

A
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24) 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
answer

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

B
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30) 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
answer

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

E
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35) 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
answer

C
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37) The ?-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.
answer

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

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

D
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40) 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
answer

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

A
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49) 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)
answer

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

A
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57) 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
answer

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

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

A
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63) 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
answer

A
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64) What product results when an aldol is dehydrated? A) conjugated alkyne B) ?-diketone C) ?-ketoester D) ?,?-unsaturated aldehyde E) ?,?-unsaturated aldehyde
answer

D
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67) 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
answer

D
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79) Predict the pKa unit of the indicated proton within +/- 1 pKa unit. A) 5 B) 11 C) 19 D) 24
answer

D
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90) 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
answer

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

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

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

C
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108) 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
answer

C
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115) In the Michael reaction, addition to the ?,?-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.
answer

C
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116) Which of the following is a nucleophile that does conjugate additions? A) CH2CHCHO B) CH2CHCN C) CH2CHCO2CH3 D) CH3CH2MgBr E) (CH3)2CuLi
answer

E
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2) What name is given to the alpha substitution of a carbonyl compound where the electrophilic component is another carbonyl compound?
answer

carbonyl condensation
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14) Provide the structure of lithium diisopropylamide.
answer

[(CH3)2CH]2N- Li+
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25) What species results when cyclopentanone is treated with lithium diisopropylamide at low temperature?
answer

the lithium enolate of cyclopentanone
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34) Provide the major organic product of the reaction shown below.
answer

acetylcyclohexanone
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36) What compound is produced in the reaction of cyclopentanone with Br2 in acetic acid?
answer

2-bromocyclopentanone
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45) What organic compounds are produced when 2-pentanone undergoes the haloform reaction upon treatment with HO- and excess Br2?
answer

butanoate and bromoform
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47) Complete the following short synthesis by providing the necessary sequence of reagents.
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1) I2 / NaOH 2) CH3OH / H+ or 2) CH2N2
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55) Provide the sequence of synthetic steps required to produce N-cyclohexyl-2-bromopropanamide from propanoic acid.
answer

1. PBr3, Br2 2. cyclohexylamine
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68) What two organic starting materials are required to produce cinnamaldehyde (PhCH=CHCHO) via a crossed aldol condensation followed by dehydration?
answer

PhCHO and CH3CHO
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71) What two molecules were condensed in an aldol reaction to produce PhCH=CHCOPh?
answer

PhCHO and PhCOCH3
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83) Name the product which results when ethyl butanoate is treated with sodium ethoxide followed by neutralization.
answer

ethyl 2-ethyl-3-oxohexanoate
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91) What additional starting material is needed to complete the following transformation?
answer

methyl propanoate
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100) Arrange the following compounds in order of increasing acidity: acetone, ethyl acetoacetate, ethyl acetate, and ethanol.
answer

ethyl acetate < acetone < ethanol < ethyl acetoacetate