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What is the name of the general reaction type that carboxylic acids, esters, and amides undergo?


A) Electrophilic acyl addition
B) Nucleophilic acyl addition
C) Nucleophilic acyl substitution
D) Electrophilic acyl substitution

E) B) and C)
F) A) and D)

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A carbonyl group, C=O, and an alkene, C=C, double bonds, are both sp2 hybridized. However, the chemistry of these two functional groups is very different. This can be explained by which of the following statements?


A) The bond angle of the carbonyl is larger than the bond angle of the alkene.
B) The electronegative oxygen of the C=O group makes this bond polar.
C) The bond of the C=C is longer that the bond of the C=O.
D) There is more steric crowding in the carbonyl than in the alkene.

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

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Why would the alcohol in the following compound need to be protected before reaction? Why would the alcohol in the following compound need to be protected before reaction? A) If it isn't protected, the product will be a carboxylic acid. B) The Grignard reagent will react with the alcohol before the ketone. C) Magnesium is Lewis acidic and will coordinate with the alcohol. D) There is no need to protect the alcohol.


A) If it isn't protected, the product will be a carboxylic acid.
B) The Grignard reagent will react with the alcohol before the ketone.
C) Magnesium is Lewis acidic and will coordinate with the alcohol.
D) There is no need to protect the alcohol.

E) A) and B)
F) B) and C)

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What reagent can be used to cleave a silyl ether protecting group?


A) NaOMe
B) MeMgBr
C) Bu4NF
D) Pd/C

E) A) and B)
F) A) and C)

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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


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

E) None of the above
F) A) and C)

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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

E) A) and C)
F) C) and D)

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Why are ketones less reactive than aldehydes?


A) Ketones are more sterically hindered.
B) Ketones are less electron deficient due to donation from the two alkyl groups.
C) The statement is false; Ketones are more reactive than aldehydes.
D) Both (a) Ketones are more sterically hindered and (b) Ketones are less electron deficient due to donation from the two alkyl groups.

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

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Rank the following compounds in order of decreasing reactivity in nucleophilic addition reactions, starting with the most reactive compound. Rank the following compounds in order of decreasing reactivity in nucleophilic addition reactions, starting with the most reactive compound. A) III > I > IV > II B) II > IV > I > III C) IV > II > III > I D) II > IV > III > I


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

E) A) and B)
F) B) and C)

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What is the major organic product in the following sequence of reactions? What is the major organic product in the following sequence of reactions? A) I B) II C) III D) IV


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

E) A) and B)
F) A) and C)

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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


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

E) All of the above
F) B) and C)

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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

E) B) and C)
F) A) and D)

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Which reagent can be used to reduce an acid chloride to an aldehyde?


A) NaBH4
B) LiAlH(OtBu) 3
C) LiAlH4
D) FeCl3

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

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Which of the following statements about organometallic reagents is not true?


A) Organometallic reagents contain a carbon atom bonded to a metal.
B) The more polar the carbon-metal bond, the more reactive the organometallic reagent.
C) Organometallic reagents react as bases and nucleophiles.
D) Organometallic reagents are strong acids that readily donate a proton to water.

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

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