Question 1

Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X (C7H14O) as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X? 2CH3 followed by CH3Br affords compound X (C7H14O) as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X?       A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" > 2CH3 followed by CH3Br affords compound X (C7H14O) as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X?       A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" > 2CH3 followed by CH3Br affords compound X (C7H14O) as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X?       A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 2

Which is the most acidic proton in the following compound?

Accepted Answer

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

Question 3

Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

Accepted Answer

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

Question 4

Why can't you prepare 2-tert-butylcyclohexanone by the following reaction? N2 reaction. C) Because tert-butyl bromide is a nucleophile. D) Because tert-butyl bromide is not a stable compound." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Because tert-butyl bromide is too basic.
B)  Because tert-butyl bromide cannot undergo an SN2 reaction.
C)  Because tert-butyl bromide is a nucleophile.
D)  Because tert-butyl bromide is not a stable compound.E) A) and D)
F) A) and C)

Question 5

Which of the following compounds is the most acidic?

Accepted Answer

A)  Ethyl acetoacetate
B)  2-Butanone
C)  1-Butanol
D)  3-PentanoneE) B) and D)
F) All of the above

Question 6

Starting with cyclohexanone,how could you prepare the diketone below?

Accepted Answer

A)  Treat cyclohexanone with a base under thermodynamic conditions.
B)  Hydrogenate cyclohexanone with Raney nickel.
C)  Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone.
D)  Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.E) B) and C)
F) B) and D)

Question 7

What is the starting material in the following reaction?

Accepted Answer

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

Question 8

The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.

Accepted Answer

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

Question 9

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Accepted Answer

A)  Sodium hydroxide
B)  Sodium methoxide
C)  Sodium tert-butoxide
D)  Sodium hydrideE) B) and D)
F) A) and D)

Question 10

Which of the following would undergo racemization under basic conditions?

Accepted Answer

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

Question 11

Which is the more stable form of acetophenone?

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  I and II are equally stableE) A) and B)
F) None of the above

Question 12

Which is the most stable form of 1,3-cyclohexanedione?

Accepted Answer

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

Question 13

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Accepted Answer

A)  An enolate
B)  An enol
C)  A tautomer
D)  An epimerE) A) and D)
F) A) and C)

Question 14

What is the missing reagent for the following reaction? 2/HOAc B) Br2/KOH C) Cl2/FeCl3 D) Br2/FeBr3" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Br2/HOAc
B)  Br2/KOH
C)  Cl2/FeCl3
D)  Br2/FeBr3E) B) and C)
F) None of the above

Question 15

The following molecule is called

Accepted Answer

A)  a 1,3-diketopentanoate.
B)  a diethyl malonate.
C)  an ethyl acetoacetate.
D)  a b-keto ester.E) None of the above
F) All of the above

Question 16

Which of the following compounds is an enol of compound X drawn below?

Accepted Answer

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

Question 17

What is the missing reagent in the reaction below? 2/AcOH B) I2/KOH C) I2 D) KOH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Br2/AcOH
B)  I2/KOH
C)  I2
D)  KOHE) B) and C)
F) C) and D)

Question 18

What is (are) the product(s) of the following reaction?

Accepted Answer

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

Question 19

What is the product of the following reaction?

Accepted Answer

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

Question 20

What is the major product of the following reaction?

Accepted Answer

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

Exam 21: Substitution Reactions of Carbonyl Compounds at the a Carbon

Which is the most acidic proton in the following compound?

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Which of the following compounds is an enol of compound X drawn below?

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Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

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What is the missing reagent in the reaction below?

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Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?

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Which is the more stable form of acetophenone?

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Which is the most stable form of 1,3-cyclohexanedione?

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What is the major product of the following reaction?

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The following molecule is called

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Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

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What is the missing reagent for the following reaction?

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What is the starting material in the following reaction?

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The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.

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Starting with cyclohexanone,how could you prepare the diketone below?

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Which of the following would undergo racemization under basic conditions?

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Which of the following compounds is the most acidic?

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What is the product of the following reaction?

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What is (are) the product(s) of the following reaction?

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Which of the following is the intermediate for halogenation of ketones under acidic conditions?

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Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X (C7H14O) as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X?

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Treatment of 2-hexanone with NaOCH₂CH₃ followed by CH₃Br affords compound X (C₇H₁₄O) as the major product.X shows a strong absorption in the IR spectrum at 1713 cm^-1,and its ¹H NMR data is given below.What is the structure of X?

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