Question 1

What is the total number of pentyl alcohols,including stereoisomers?

Accepted Answer

A)   7
B)   8
C)   9
D)   10
E)   11

Question 2

Which of the following could be used to synthesize 1-bromopentane?

Accepted Answer

A)   CH3CH2CH2CH=CH2 + HBr →\rightarrow→ 
B)   CH3CH2CH2CH2CH2OH + PBr3  →\rightarrow→ 
C)   CH3CH2CH2CH2CH2OH + NaBr  →\rightarrow→ 
D)   CH3CH2CH2CH2CH2OH + Br2  →\rightarrow→ 
E)   CH3CH2CH2CH=CH2 + Br2 →\rightarrow→

Question 3

Draw all of the enantiomeric forms corresponding to the formula C5H12O.

Accepted Answer

Question 4

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 5

When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl2)in the presence of a 3° amine,the resulting alkyl chloride is produced with _____________ of configuration.

Accepted Answer

Question 6

What is the product of the reaction of propyl alcohol with (CH3) 3SiCl in the presence of a tertiary amine?

Accepted Answer

A)   CH3CH2CH2Si(CH3) 3
B)   (CH3) 2CHSi(CH3) 3
C)   CH3CH2CH2OSi(CH3) 3
D)   (CH3) 2CHOSi(CH3) 3
E)   (CH3CH2CH2) 3SiOH C

Question 7

Which of the following could be used to synthesize 2-bromobutane?

Accepted Answer

A)   CH3CH2CH ≡ \equiv≡ CH2 + Br2 (aq)  →\rightarrow→ 
B)   CH3CH2C ≡ \equiv≡ CH3 + HBr  →\rightarrow→ 
C)   CH3CH2C ≡ \equiv≡ CH + HBr  →\rightarrow→ 
D)   CH3CH2C ≡ \equiv≡ CH + Br2  →\rightarrow→ 
E)   More than one of the above

Question 8

Propose a mechanism for the following transformation:

Accepted Answer

The answer of Propose a mechanism for the following transformation:...

Question 9

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 10

The following reaction, N1-type reaction involving the protonated alcohol as the substrate. B)  an SN2-type reaction involving the protonated alcohol as the substrate. C)  an E1-type reaction involving the protonated alcohol as the substrate. D)  an E2-type reaction involving the protonated alcohol as the substrate. E)  an epoxidation reaction." class="answers-bank-image d-inline" rel="preload" > is probably:

Accepted Answer

A)   an SN1-type reaction involving the protonated alcohol as the substrate.
B)   an SN2-type reaction involving the protonated alcohol as the substrate.
C)   an E1-type reaction involving the protonated alcohol as the substrate.
D)   an E2-type reaction involving the protonated alcohol as the substrate.
E)   an epoxidation reaction.

Question 11

Which of the following statements is NOT true of ethers?

Accepted Answer

A)   Ethers are generally unreactive molecules toward reagents other than strong acids.
B)   Ethers generally have lower boiling points than alcohols of a corresponding molecular weight.
C)   Ethers generally have much lower water solubilities than alcohols with a corresponding molecular weight.
D)   Ethers can generally be cleaved by heating them with strong acids.
E)   Ethers form peroxides when allowed to stand in the presence of oxygen. C

Question 12

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 13

Propose a mechanism for the following transformation:

Accepted Answer

The answer of Propose a mechanism for the following transformation:...

Question 14

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

Accepted Answer

A)   CH3CH2CH2CH2CH3
B)   CH3CH2CH2CH2OH
C)   CH3CH2CH2OCH3
D)   CH3CH2CH2Cl
E)   CH3CH2OCH2CH3

Question 15

The number of secondary alcohols corresponding to the formula C5H12O,counting stereoisomers separately,is:

Accepted Answer

A)   1
B)   2
C)   3
D)   4
E)   5

Question 16

If trans-2-butene is treated with meta-chloroperbenzoic acid what is the final product?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   None of the above

Question 17

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 18

Which of the alcohols listed below would you expect to react most rapidly with HBr?

Accepted Answer

A)   CH3CH2CH2CH2CH2CH2OH
B)   (CH3CH2) 2CH2CH2OH
C)   (CH3CH2) 2CHOHCH3
D)   CH3CH2CH2CH2CH2OH
E)   (CH3CH2) 2C(CH3) OH

Question 19

Give the correct IUPAC name corresponding to the following structure:

Accepted Answer

(R)-3-ethy...

Question 20

Which reagent(s) would transform propyl alcohol into propyl bromide?

Accepted Answer

A)   Concd.HBr and heat
B)   PBr3
C)   NaBr/H2O and heat
D)   More than one of these
E)   All of these

Exam 11: Alcohols and Ethers

What is the total number of pentyl alcohols,including stereoisomers?

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Which of the following could be used to synthesize 1-bromopentane?

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Draw all of the enantiomeric forms corresponding to the formula C5H12O.

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Complete the following reaction sequence,giving structural details of all key intermediates:

Correct AnswerverifiedShow Answer

When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl2)in the presence of a 3° amine,the resulting alkyl chloride is produced with _____________ of configuration.

Correct AnswerverifiedShow Answer

What is the product of the reaction of propyl alcohol with (CH3) 3SiCl in the presence of a tertiary amine?

Correct AnswerverifiedC

Which of the following could be used to synthesize 2-bromobutane?

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Propose a mechanism for the following transformation:

Correct Answerverified11ea9a02_1b4c_03e4_8bb6_c51e19f30e47_TB5901_00

Complete the following reaction sequence,giving structural details of all key intermediates:

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The following reaction, is probably:

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Which of the following statements is NOT true of ethers?

Correct AnswerverifiedC

Complete the following reaction sequence,giving structural details of all key intermediates:

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Propose a mechanism for the following transformation:

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Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

Correct AnswerverifiedShow Answer

The number of secondary alcohols corresponding to the formula C5H12O,counting stereoisomers separately,is:

Correct AnswerverifiedShow Answer

If trans-2-butene is treated with meta-chloroperbenzoic acid what is the final product?

Correct AnswerverifiedShow Answer

Complete the following reaction sequence,giving structural details of all key intermediates:

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Which of the alcohols listed below would you expect to react most rapidly with HBr?

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Give the correct IUPAC name corresponding to the following structure:

Correct Answerverified(R)-3-ethy...View AnswerShow Answer

Which reagent(s) would transform propyl alcohol into propyl bromide?

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Draw all of the enantiomeric forms corresponding to the formula C₅H₁₂O.

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When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl₂)in the presence of a 3° amine,the resulting alkyl chloride is produced with _____________ of configuration.

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What is the product of the reaction of propyl alcohol with (CH₃) ₃SiCl in the presence of a tertiary amine?

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C

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11ea9a02_1b4c_03e4_8bb6_c51e19f30e47_TB5901_00

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C

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The number of secondary alcohols corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

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(R)-3-ethy...
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