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When the 1,7-diester CH3O2CCH2CH2CH(CH3) CH2CH2CO2CH3 is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?


A) an acyclic β-diketone
B) an acyclic β-ketoacid
C) an acyclic β-diester
D) a cyclic β-ketoester
E) a cyclic β-diketone

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Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.

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When compared to the keto form,the enol form of which of the following compounds is most stable? When compared to the keto form,the enol form of which of the following compounds is most stable? A) I B) II C) III D) IV E) V


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

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Provide the major organic product of the following. Provide the major organic product of the following.

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When compound X is heated,PhCOCH(CH3)2 and CO2 are produced.Offer a structure for compound X.

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A student proposed the following synthesis.Why did it fail? A student proposed the following synthesis.Why did it fail? A) The use of LDA results in the thermodynamic product instead of the desired kinetic product. B) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate. C) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone. D) The tertiary bromide is too sterically hindered to be attacked by the enolate. E) Instead of 2-methyl-2-bromopentane,2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur.


A) The use of LDA results in the thermodynamic product instead of the desired kinetic product.
B) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate.
C) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone.
D) The tertiary bromide is too sterically hindered to be attacked by the enolate.
E) Instead of 2-methyl-2-bromopentane,2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur.

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Use an asterisk to indicate the most electron-rich carbon in the molecule below. Use an asterisk to indicate the most electron-rich carbon in the molecule below.

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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)

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Which of the labeled hydrogen atoms in the following structure is the most acidic? Which of the labeled hydrogen atoms in the following structure is the most acidic? A) 1 B) 2 C) 3 D) 4 E) 5


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

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Provide a detailed,stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone,hydroxide and iodine.

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

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


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

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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.

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

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Explain why the following acid cannot be prepared by the malonic ester synthesis. Explain why the following acid cannot be prepared by the malonic ester synthesis.

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Since bromobenzene is needed to prepare ...

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Provide a detailed,stepwise mechanism for the α-bromination of acetone in base.

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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 materials are needed to prepare the following product? What materials are needed to prepare the following product? A) I B) II C) III D) IV E) V


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

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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 major organic product of the following reaction. Provide the major organic product of the following reaction.

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