Question 1

What is the hybridization of the oxygen atom in dialkyl ethers?

Accepted Answer

A)   sp3
B)   sp2
C)   sp
D)   s
E)   p

Question 2

Which pair of reagents would produce the highest yield of (R) -2-ethoxybutane?

Accepted Answer

A)   sodium (S) -2-butoxide + iodoethane
B)   sodium (R) -2-butoxide + iodoethane
C)   sodium ethoxide + (S) -2-iodobutane
D)   sodium ethoxide + (R) -2-iodobutane
E)   Both B and C would work equally well.

Question 3

Suggest a reasonable mechanism for the reaction shown below.

Accepted Answer

The answer of Suggest a reasonable mechanism for the reaction...

Question 4

Provide the major organic product in the reaction below.

Accepted Answer

The answer of Provide the major organic product in the...

Question 5

What compound is formed when ethylene oxide is reacted with n-pentyllithium followed by treatment with aqueous acid?

Accepted Answer

A)   1-heptanol
B)   2-heptanol
C)   heptanal
D)   2-heptanone
E)   pentanal

Question 6

Show the reagents necessary to prepare trans-2-deuteriocyclohexan-1-ol from cyclohexene.

Accepted Answer

The answer of Show the reagents necessary to prepare trans-2-deuteriocyclohexan-1-ol...

Question 7

When trans-hex-3-ene is treated with PhCO3H, the major organic product is ________.

Accepted Answer

A)   a meso epoxide
B)   a 1:1 mixture of enantiomeric epoxides
C)   a meso diol
D)   a 1:1 mixture of enantiomeric diols
E)   hexan-3-ol

Question 8

Provide the IUPAC name of the compound shown below.

Accepted Answer

1,1-dietho...

Question 9

Which of the following reactions or series of reactions will lead to the formation of methoxycyclohexane?

Accepted Answer

A)   
B)   
C)   
D)   
E)    D

Question 10

Show the reagents necessary to perform the synthesis shown below.

Accepted Answer

1) CH₃CH₂MgB...

Question 11

Show the reagents necessary to prepare trans-1,2-cyclopentanediol from cyclopentene.

Accepted Answer

The answer of Show the reagents necessary to prepare trans-1,2-cyclopentanediol...

Question 12

Provide the major organic product(s) in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) in the...

Question 13

Propose a structure for the ether of formula C4H10O with the following 1H NMR signals:
δ 0.95 (triplet, 3H), 1.52 (multiplet, 2H), 3.30 (singlet, 3H), 3.40 (triplet, 2H) (ppm).

Accepted Answer

Question 14

Provide the major organic product in the reaction below.
HOCH2(CH2)2CH2Br

Accepted Answer

Question 15

What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent)  is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H3O+?

Accepted Answer

A)   The alkyl group from the Grignard reagent will be bonded to the α-carbon of the alcohol product.
B)   The alkyl group from the Grignard reagent will be bonded to the β-carbon of the alcohol product.
C)   The alkyl group from the Grignard reagent will form an ether product rather than an alcohol product.
D)   Two equivalents of the Grignard will result in the bonding of two alkyl groups to the α-carbon of the alcohol product.
E)   The epoxide will protonate the Grignard reagent resulting an alkane product.

Question 16

Provide the major organic product of the following.

Accepted Answer

The answer of Provide the major organic product of the...

Question 17

Provide the major organic product in the reaction below.

Accepted Answer

The answer of Provide the major organic product in the...

Question 18

Which of the following is not a property of ethers?

Accepted Answer

A)   They dissolve a wide range of polar substances.
B)   They have relatively high boiling points for their molecular weights.
C)   They are nonhydroxylic.
D)   They dissolve a wide range of nonpolar substances.
E)   They are normally unreactive toward strong bases. B

Question 19

Show the reagents necessary to prepare 1-ethoxy-1-methylcyclopentane from 1-methylcyclopentene.

Accepted Answer

1) Hg(OAc)...

Question 20

Provide the major organic product in the reaction below.

Accepted Answer

The answer of Provide the major organic product in the...

Exam 14: Ethers, Epoxides, and Thioethers

What is the hybridization of the oxygen atom in dialkyl ethers?

Correct AnswerverifiedShow Answer

Which pair of reagents would produce the highest yield of (R) -2-ethoxybutane?

Correct AnswerverifiedShow Answer

Suggest a reasonable mechanism for the reaction shown below.

Correct AnswerverifiedShow Answer

Provide the major organic product in the reaction below.

Correct AnswerverifiedShow Answer

What compound is formed when ethylene oxide is reacted with n-pentyllithium followed by treatment with aqueous acid?

Correct AnswerverifiedShow Answer

Show the reagents necessary to prepare trans-2-deuteriocyclohexan-1-ol from cyclohexene.

Correct AnswerverifiedShow Answer

When trans-hex-3-ene is treated with PhCO3H, the major organic product is ________.

Correct AnswerverifiedShow Answer

Provide the IUPAC name of the compound shown below.

Correct Answerverified1,1-dietho...View AnswerShow Answer

Which of the following reactions or series of reactions will lead to the formation of methoxycyclohexane?

Correct AnswerverifiedD

Show the reagents necessary to perform the synthesis shown below.

Correct Answerverified1) CH3CH2MgB...View AnswerShow Answer

Show the reagents necessary to prepare trans-1,2-cyclopentanediol from cyclopentene.

Correct AnswerverifiedShow Answer

Provide the major organic product(s) in the reaction below.

Correct AnswerverifiedShow Answer

Propose a structure for the ether of formula C4H10O with the following 1H NMR signals: δ 0.95 (triplet, 3H), 1.52 (multiplet, 2H), 3.30 (singlet, 3H), 3.40 (triplet, 2H) (ppm).

Correct AnswerverifiedShow Answer

Provide the major organic product in the reaction below. HOCH2(CH2)2CH2Br

Correct AnswerverifiedShow Answer

What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H3O+?

Correct AnswerverifiedShow Answer

Provide the major organic product of the following.

Correct Answerverified11eab5e1_c9a6_281b_9bae_2b8dd5515d98_TB6199_00

Provide the major organic product in the reaction below.

Correct AnswerverifiedShow Answer

Which of the following is not a property of ethers?

Correct AnswerverifiedB

Show the reagents necessary to prepare 1-ethoxy-1-methylcyclopentane from 1-methylcyclopentene.

Correct Answerverified1) Hg(OAc)...View AnswerShow Answer

Provide the major organic product in the reaction below.

Correct AnswerverifiedShow Answer

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When trans-hex-3-ene is treated with PhCO₃H, the major organic product is ________.

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1,1-dietho...
View Answer

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D

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1) CH₃CH₂MgB...
View Answer

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Propose a structure for the ether of formula C₄H₁₀O with the following ¹H NMR signals: δ 0.95 (triplet, 3H), 1.52 (multiplet, 2H), 3.30 (singlet, 3H), 3.40 (triplet, 2H) (ppm).

Correct Answer
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Provide the major organic product in the reaction below. HOCH₂(CH₂)₂CH₂Br

Correct Answer
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What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H₃O⁺?

Correct Answer
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11eab5e1_c9a6_281b_9bae_2b8dd5515d98_TB6199_00

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B

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1) Hg(OAc)...
View Answer

Correct Answer
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