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Draw the most stable enol tautomer of the ketone shown below. Draw the most stable enol tautomer of the ketone shown below.

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Give the major product for the following reaction. Give the major product for the following reaction.

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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

F) A) and B)
G) A) and C)

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Rank the following compounds in order of increasing acidity of their a-Hs,least acidic to most acidic: CH3CH2CON(CH3)2,PhCOCH2CHO,CH3CH2CO2CH2CH3,and PhCOCH2CO2CH2CH3.

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CH3CH2CON(CH...

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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

F) B) and E)
G) A) and D)

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What is the major organic product of the following aldol addition? What is the major organic product of the following aldol addition?   A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) A) and C)
G) C) and E)

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What two molecules were condensed in an aldol reaction to produce (CH3)3CCH What two molecules were condensed in an aldol reaction to produce (CH<sub>3</sub>)<sub>3</sub>CCH   CHCOCH<sub>3</sub>? CHCOCH3?

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Provide a detailed,stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.

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Give the major product for the following reaction. Give the major product for the following reaction.

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What is the major organic product from the following reaction? What is the major organic product from the following reaction?   A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) D) and E)
G) None of the above

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Give the major product for the following reaction. Give the major product for the following reaction.

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Give the major product for the following reaction. Give the major product for the following reaction.   A)    B)    C)    D)    E)


A) Give the major product for the following reaction.   A)    B)    C)    D)    E)
B) Give the major product for the following reaction.   A)    B)    C)    D)    E)
C) Give the major product for the following reaction.   A)    B)    C)    D)    E)
D) Give the major product for the following reaction.   A)    B)    C)    D)    E)
E) Give the major product for the following reaction.   A)    B)    C)    D)    E)

F) A) and B)
G) A) and D)

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Fill in the empty boxes. Fill in the empty boxes.

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What is the major organic product of the following reaction? What is the major organic product of the following reaction?   A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) A) and B)
G) A) and C)

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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

F) B) and E)
G) C) and D)

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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

F) D) and E)
G) All of the above

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Provide the major organic product(s)of the reaction shown below. Provide the major organic product(s)of the reaction shown below.

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Provide the structure of the major organic product that results when 4-methylhexanal is heated in base and undergoes and aldol addition followed by a dehydration.

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Which of the following molecules cannot generate an enolate? Which of the following molecules cannot generate an enolate?   A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) B) and E)
G) A) and B)

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Give the major product for the following reaction. Give the major product for the following reaction.

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