Question 1

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

Accepted Answer

A)  NaBH4
B)  LiAlH(OtBu) 3
C)  LiAlH4
D)  FeCl3E) A) and B)
F) A) and C)

Question 2

What are the two steps in a nucleophilic addition mechanism?

Accepted Answer

A)  Nucleophilic attack followed by protonation
B)  Nucleophilic attack followed by deprotonation
C)  Nucleophilic attack followed by substitution
D)  Nucleophilic attack followed by eliminationE) All of the above
F) A) and B)

Question 3

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

Accepted Answer

A)  NaBH4
B)  LiAlH(OtBu) 3
C)  LiAlH4
D)  FeCl3E) A) and D)
F) A) and C) C

Question 4

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and D)
F) All of the above

Question 5

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) A) and B)

Question 6

The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because

Accepted Answer

A)  the acid chloride contains a better leaving group
B)  the aldehyde is more easily oxidized
C)  the carbonyl of the aldehyde is more positive
D)  the carbonyl of the aldehyde is less hinderedE) All of the above
F) B) and D)

Question 7

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) A) and B)

Question 8

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

Accepted Answer

A)  NaOMe
B)  MeMgBr
C)  Bu4NF
D)  Pd/CE) B) and C)
F) All of the above

Question 9

What is the product of the following reaction?

Accepted Answer

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

Question 10

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?

Accepted Answer

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) A) and C) B

Question 11

Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity,starting with the most polar.  I > III B) II > III > I C) III > I > II D) III > II > I" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  II > I > III
B)  II > III > I
C)  III > I > II
D)  III > II > IE) A) and D)
F) B) and C)

Question 12

What is the product of the following reaction?

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  Only I and IIE) None of the above
F) A) and B)

Question 13

Why are ketones less reactive than aldehydes?

Accepted Answer

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 Ketones are more sterically hindered and Ketones are less electron deficient due to donation from the two alkyl groupsE) A) and C)
F) A) and B)

Question 14

What is the missing reagent in the reaction below? 4/CH3OH B) H2,Pd-C C) LiAlH4 then H2O D) MeMgBr then H2O" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  NaBH4/CH3OH
B)  H2,Pd-C
C)  LiAlH4 then H2O
D)  MeMgBr then H2OE) A) and C)
F) All of the above

Question 15

Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution reactions,starting with the least reactive compound.

Accepted Answer

A)  III 
B)  II 
C)  III 
D)  II < I < IIIE) A) and B)
F) A) and C)

Question 16

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) B) and C) B

Question 17

What is the major product from the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) All of the above

Question 18

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) All of the above
F) A) and D)

Question 19

If the starting material has no stereogenic centers,when carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed,what will the composition of the product mixture be?

Accepted Answer

A)  Forms a racemic mixture of the two possible enantiomers
B)  Forms more of one enantiomer than another because of steric reactions around the carbonyl
C)  Forms more of one enantiomer than another depending on the temperature of the reaction
D)  Forms different products depending on the solvent usedE) A) and D)
F) A) and C)

Question 20

What is the product of the following reaction?

Accepted Answer

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

Exam 17: Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Correct AnswerverifiedShow Answer

What are the two steps in a nucleophilic addition mechanism?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedC

What is the major organic product of the following reaction?

Correct AnswerverifiedShow Answer

What is the major organic product of the following reaction?

Correct AnswerverifiedShow Answer

The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because

Correct AnswerverifiedShow Answer

What is the major organic product of the following reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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?

Correct AnswerverifiedB

Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity,starting with the most polar.

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

Why are ketones less reactive than aldehydes?

Correct AnswerverifiedShow Answer

What is the missing reagent in the reaction below?

Correct AnswerverifiedShow Answer

Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution reactions,starting with the least reactive compound.

Correct AnswerverifiedShow Answer

What is the major organic product of the following reaction?

Correct AnswerverifiedB

What is the major product from the following reaction?

Correct AnswerverifiedShow Answer

What is the major organic product of the following reaction?

Correct AnswerverifiedShow Answer

If the starting material has no stereogenic centers,when carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed,what will the composition of the product mixture be?

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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C

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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?

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B

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B

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If the starting material has no stereogenic centers,when carbonyl compounds are reduced with a reagent such as LiAlH₄ or NaBH₄ and a new stereogenic center is formed,what will the composition of the product mixture be?

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