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What are the two steps in a nucleophilic addition mechanism?


A) Nucleophilic attack followed by protonation.
B) Nucleophilic attack followed by deprotonation.
C) Nucleophilic attack followed by substitution.
D) Nucleophilic attack followed by elimination.

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

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What reagent would be used to reduce an amide to an amine?


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

E) None 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 D)
F) C) and D)

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

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Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate II) benzoylchloride III) benzamide


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

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

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Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity, starting with the most polar. CH3CH2MgBrCH3CH2Li(CH3CH2) 2CuLi I  II  III \begin{array} { c c c } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { MgBr } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Li } & \left( \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \right) _ { 2 } \mathrm { CuLi } \\\text { I } & \text { II } & \text { III }\end{array}


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

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

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

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Both LiAlH4 and NaBH4 are reducing agents. Which statement about these reagents is true?


A) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent.
B) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent.
C) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent.
D) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent.

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

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What is the purpose of a silyl ether?


A) To protect esters from organometallic reagents and other reagents
B) To protect ketones from organometallic reagents and other reagents
C) To protect alcohols from organometallic reagents and other reagents
D) To prevent the formation of carboxylic acids

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

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What is the name of the general reaction type that aldehydes and ketones undergo?


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

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

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


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

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

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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

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

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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 B)
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) B) and D)
F) None of the above

Correct Answer

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What is the missing reagent in the reaction below? What is the missing reagent in the reaction below? A) PhMgBr then H<sub>2</sub>O B) Benzene, AlCl<sub>3</sub> C) Ph<sub>2</sub>CuLi then H<sub>2</sub>O D) PhLi then H<sub>2</sub>O


A) PhMgBr then H2O
B) Benzene, AlCl3
C) Ph2CuLi then H2O
D) PhLi then H2O

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

Correct Answer

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What is the missing reagent in the reaction below? What is the missing reagent in the reaction below? A) Et<sub>2</sub>CuLi then H<sub>2</sub>O B) EtMgBr then H<sub>2</sub>O C) NaBH<sub>4</sub>/CH<sub>3</sub>OH D) H<sub>2</sub>, Pd-C


A) Et2CuLi then H2O
B) EtMgBr then H2O
C) NaBH4/CH3OH
D) H2, Pd-C

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

Correct Answer

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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) B) and D)

Correct Answer

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What carbonyl compound and Grignard reagent could be used to prepare 2-butanol? CH3CHO/CH3CH2MgBrCH3CH2CHO/CH3MgBrCH3COCH3/CH3MgBr\mathrm { CH } _ { 3 } \mathrm { CHO } / \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { MgBr } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHO } / \mathrm { CH } _ { 3 } \mathrm { MgBr } \quad \mathrm { CH } _ { 3 } \mathrm { COCH } _ { 3 } / \mathrm { CH } _ { 3 } \mathrm { MgBr }  I  II  III \begin{array} { c c c } \text { I } &&&&&&&& \text { II } &&&&&&&&\text { III }\end{array}


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

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

Correct Answer

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What is the starting material in the reaction below? What is the starting material in the reaction below? A) Bromobenzene B) Benzyl bromide C) Benzoic acid D) Lithium benzoate


A) Bromobenzene
B) Benzyl bromide
C) Benzoic acid
D) Lithium benzoate

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

Correct Answer

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