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A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with


A) bromine with acetic acid.
B) bromine and aqueous hydroxide ion.
C) THF,LDA at -78 °C followed by reaction with bromine.
D) base and methyl bromide.

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


A) 3-Heptanone
B) 2-Pentanone
C) 3-Hexanone
D) Cyclohexanone

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Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form? Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?   A) I B) II C) III D) IV


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

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Which is the more stable form of acetophenone? Which is the more stable form of acetophenone?   A) Only I B) Only II C) Only III D) I and II are equally stable


A) Only I
B) Only II
C) Only III
D) I and II are equally stable

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B

If you want to form a thermodynamic enolate,you want to


A) keep the reaction as cold as possible.
B) use an aprotic solvent such as THF.
C) use a protic solvent such as ethanol.
D) use a carboxylic acid.

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Which is the most stable form of 1,3-cyclohexanedione? Which is the most stable form of 1,3-cyclohexanedione?   A) I B) II C) III D) IV


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

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What is the structure of X,product of the following reaction? What is the structure of X,product of the following reaction?   A) I B) II C) III D) IV


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

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Which is the thermodynamic enolate of 2-methylcyclohexanone? Which is the thermodynamic enolate of 2-methylcyclohexanone?   A) I B) II C) III D) IV


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

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What is the starting material in the following reaction? What is the starting material in the following reaction?   A) I B) II C) III D) IV


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

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


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

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The reaction below is a direct enolate alkylation.It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides.Pick the statement that best explains this observation. The reaction below is a direct enolate alkylation.It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides.Pick the statement that best explains this observation.   A) The nucleophilic enolate requires a reaction center that has a positive charge. B) Hindered alkyl halides do not undergo S<sub>N</sub>1 reactions. C) Hindered alkyl halides do not undergo S<sub>N</sub>2 reactions. D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.


A) The nucleophilic enolate requires a reaction center that has a positive charge.
B) Hindered alkyl halides do not undergo SN1 reactions.
C) Hindered alkyl halides do not undergo SN2 reactions.
D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.

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C

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


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

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Which of the following is a possible enol form of 2-butanone? Which of the following is a possible enol form of 2-butanone?   A) I B) II C) III D) II and III


A) I
B) II
C) III
D) II and III

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What is the starting material required to accomplish the following transformation? What is the starting material required to accomplish the following transformation?   A) I B) II C) III D) IV


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

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What is (are) the product(s) of the following reaction? What is (are) the product(s) of the following reaction?   A) Only I B) Only II C) Only III D) Only I and III


A) Only I
B) Only II
C) Only III
D) Only I and III

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D

Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?


A) The ketone undergoes a Bayer-Villigar oxidation.
B) The ketone is reduced.
C) The ketone undergoes an Aldol reaction.
D) The bromine helps to stabilize the second enolate,making the product more acidic than the starting material.

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Select the appropriate sequence of reactions to accomplish the following synthesis. Select the appropriate sequence of reactions to accomplish the following synthesis.   A) [1] Br<sub>2</sub>,CH<sub>3</sub>CO<sub>2</sub>H; [2] Li<sub>2</sub>CO<sub>3</sub>,LiBr,DMF; [3] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br B) [1] Br<sub>2</sub>,CH<sub>3</sub>CO<sub>2</sub>H; [2] Mg,Et<sub>2</sub>O; [3] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br C) [1] LDA; [2] BrCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br; [3] NaOEt D) [1] NaOEt; [2] BrCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br; [3] LDA


A) [1] Br2,CH3CO2H; [2] Li2CO3,LiBr,DMF; [3] CH3CH2CH2CH2Br
B) [1] Br2,CH3CO2H; [2] Mg,Et2O; [3] CH3CH2CH2CH2Br
C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt
D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA

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Will acetone be completely deprotonated by potassium tert-butoxide?


A) Yes
B) No

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Which of the following is the intermediate for halogenation of ketones under acidic conditions?


A) An enolate
B) An enol
C) A tautomer
D) An epimer

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Which of the following is the most acidic compound? Which of the following is the most acidic compound?   A) I B) II C) III D) IV


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

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