Question 1

The products from  are:

Accepted Answer

A)   
B)   
C)   
D)   
E)   no reactionF) All of the above
G) B) and D)

Question 2

An oxime can be produced by the reaction of an aldehyde and:

Accepted Answer

A)   hydroxylamine
B)   hydrazine
C)   methylamine
D)   phenylhydrazine
E)   semicarbazideF) B) and E)
G) C) and D) A

Question 3

In the mechanism for acid catalyzed hemiacetal formation, the first step is:

Accepted Answer

A)   protonation of the carbonyl oxygen
B)   nucleophilic attack at the carbonyl carbon
C)   protonation of the oxygen of the alcohol
D)   nucleophilic attack at the carbon of the alcohol
E)   elimination of a water moleculeF) A) and D)
G) D) and E)

Question 4

The enol tautomer of 3-pentanone is:

Accepted Answer

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

Question 5

Which of the following compounds is a hemiacetal?

Accepted Answer

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

Question 6

Which statement about the mechanism of imine formation from a primary amine and an aldehyde or ketone is false?

Accepted Answer

A)   The first steps involve addition of the amine to the carbonyl carbon to form a tetrahedral intermediate.
B)   The last steps involve elimination of water to form a carbon-nitrogen p-bond.
C)   All steps are reversible.
D)   The reaction involves SN2 displacement of the carbonyl oxygen by the amine nitrogen.
E)   The reaction does not require a strong acid catalyst.F) C) and E)
G) A) and D)

Question 7

Which of the following molecules has the highest boiling point?

Accepted Answer

A)   o-xylene
B)   m-xylene
C)   p-xylene
D)   benzaldehyde
E)   benzyl alcoholF) A) and D)
G) A) and C)

Question 8

What reaction will produce the following product?

Accepted Answer

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

Question 9

Which of the following compounds will give a positive silver mirror test (Tollens' test) ?

Accepted Answer

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

Question 10

The expected order of boiling points of the following is: 2>1 B)  2>1>3 C)  2>3>1 D)  1>2>3 E)  1>3>2" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   3>2>1
B)   2>1>3
C)   2>3>1
D)   1>2>3
E)   1>3>2F) A) and C)
G) All of the above

Question 11

What statement is false relative to the nucleophilic additions?

Accepted Answer

A)   When a weak nucleophile is present, the reaction can be catalyzed by acid.
B)   The nucleophile attacks the trigonal carbon of the carbonyl group.
C)   Ketones are more reactive than aldehydes.
D)   Nucleophiles that add irreversibly are poor leaving groups.
E)   Nucleophiles can be classified as those that add reversibly to carbonyl compounds and those that add irreversibly.F) C) and D)
G) A) and E)

Question 12

What Grignard reagent and carbonyl compound react to give benzyl alcohol after treatment with aqueous acid?

Accepted Answer

A)   phenyl magnesium bromide and formaldehyde
B)   phenyl magnesium bromide and oxirane
C)   benzaldehyde and methyl magnesium bromide
D)   benzaldehyde and ethyl magnesium chloride
E)   acetophenone and methyl magnesium chlorideF) B) and D)
G) B) and C)

Question 13

Which reagents would you use to accomplish the following conversion? 4, H2O B)  LiAlH4, ether; then H3O+ C)  H2, Pt D)  all of these E)  none of these" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   NaBH4, H2O
B)   LiAlH4, ether; then H3O+
C)   H2, Pt
D)   all of these
E)   none of theseF) C) and D)
G) A) and B)

Question 14

The number of a-hydrogens in  is:

Accepted Answer

A)   1
B)   3
C)   4
D)   8
E)   14F) C) and D)
G) A) and E)

Question 15

Which of the following reactions will produce a cyanohydrin?

Accepted Answer

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

Question 16

How many hydrogens in the following compound will be exchanged for deuterium upon reaction with D2O and an acid catalyst? 2O and an acid catalyst?   A)  0 B)  2 C)  4 D)  5 E)  8" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   0
B)   2
C)   4
D)   5
E)   8F) A) and B)
G) D) and E)

Question 17

Which reagent will accomplish the following transformation? 3, H2SO4 C)  CH3MgBr D)  NaBH4 E)  H2, Pd" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   NaOH
B)   CrO3, H2SO4
C)   CH3MgBr
D)   NaBH4
E)   H2, PdF) All of the above
G) B) and C)

Question 18

The IUPAC name for the following molecule is:

Accepted Answer

A)   3-ethyl-1-phenyl-3-pentenone
B)   3-ethyl-5-phenyl-2-penten-4-one
C)   allyl benzyl ketone
D)   (
E)  -3-ethyl-1-phenyl-3-penten-2-one
E)   (Z) -3-ethyl-1-phenyl-3-penten-2-oneF) All of the above
G) A) and C)

Question 19

What class of compound most closely resembles an acetal in its reactivity with CH3MgBr?

Accepted Answer

A)   ethers
B)   aldehydes
C)   ketones
D)   alcohols
E)   thiolsF) B) and E)
G) A) and B)

Question 20

Which of the hydrogens in the following molecule are most acidic? The hydrogens on carbon

Accepted Answer

A)   1
B)   2
C)   3
D)   4
E)   5F) B) and E)
G) A) and D)

Exam 9: Aldehydes and Ketones

The products from are:

Correct AnswerverifiedShow Answer

An oxime can be produced by the reaction of an aldehyde and:

Correct AnswerverifiedA

In the mechanism for acid catalyzed hemiacetal formation, the first step is:

Correct AnswerverifiedShow Answer

The enol tautomer of 3-pentanone is:

Correct AnswerverifiedShow Answer

Which of the following compounds is a hemiacetal?

Correct AnswerverifiedShow Answer

Which statement about the mechanism of imine formation from a primary amine and an aldehyde or ketone is false?

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Which of the following molecules has the highest boiling point?

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What reaction will produce the following product?

Correct AnswerverifiedB

Which of the following compounds will give a positive silver mirror test (Tollens' test) ?

Correct AnswerverifiedD

The expected order of boiling points of the following is:

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What statement is false relative to the nucleophilic additions?

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What Grignard reagent and carbonyl compound react to give benzyl alcohol after treatment with aqueous acid?

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Which reagents would you use to accomplish the following conversion?

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The number of a-hydrogens in is:

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Which of the following reactions will produce a cyanohydrin?

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How many hydrogens in the following compound will be exchanged for deuterium upon reaction with D2O and an acid catalyst?

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Which reagent will accomplish the following transformation?

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The IUPAC name for the following molecule is:

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What class of compound most closely resembles an acetal in its reactivity with CH3MgBr?

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Which of the hydrogens in the following molecule are most acidic? The hydrogens on carbon

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A

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B

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D

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How many hydrogens in the following compound will be exchanged for deuterium upon reaction with D₂O and an acid catalyst?

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What class of compound most closely resembles an acetal in its reactivity with CH₃MgBr?

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