Deck 13: Alcohols,phenols,and Thiols: Ethers and Sulfides

Question 1

Which of the following is not a property of a protecting group?

A)change the reactivity of a functional group
B)inert to reaction conditions
C)becomes a permanent part of the product
D)alters the mechanism of the desired reaction
E)all of these are properties of a protecting group

Answer 1

becomes a permanent part of the product

Question 2

Instructions: To answer the following question(s),consider the reaction below.

Refer to instructions.Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary,secondary,or tertiary.

Answer 2

(R)-heptan-2-ol,secondary

Question 3

Instructions: Consider the reaction below to answer the following question.

Refer to instructions.Mechanistically,the Williamson ether synthesis outlined above is:

A)an E1 process
B)an S_N1 process
C)an E2 process
D)an S_N2 process

Answer 3

an S_N2 process

Question 4

What is the IUPAC name of the following compound?

A)cyclohexen-3-ol
B)cyclohexen-2-ol
C)cyclohex-1-en-3-ol
D)cyclohex-2-en-1-ol

Question 5

Instructions: To answer the following question(s),consider the reaction below.
Refer to instructions.The conversion of an alcohol into an alkyl chloride by reaction with SOCl₂ is an example of:

A)an E1 process
B)an S_N1 process
C)an E2 process
D)an S_N2 process

Question 6

Which of the following are ethers?

A)only 1 and 2
B)only 1 and 4
C)only 1,2 and 3
D)all of these are ethers

Question 7

Instructions: To answer the following question(s),consider the reaction below.
Refer to instructions.The alcohol product is classified as a:

A)1 ^$\circ$ alcohol
B)2 ^$\circ$ alcohol
C)3 ^$\circ$ alcohol
D)4 ^$\circ$ alcohol

Question 8

Addition of chlorotrimethylsilane to an alcohol

A)results in an S_N1 reaction.
B)requires acidic reaction conditions.
C)is sterically hindered by the three methyl groups.
D)results in the formation of an ether.
E)produces a more reactive species.

Question 9

Instructions: Consider the Grignard reaction below to answer the following question(s).

Refer to instructions.If a secondary alcohol were desired as a product of the reaction,B should be replaced with

A)an ester
B)an aldehyde
C)formaldehyde (methanal)
D)a primary alcohol

Question 10

Which of the following is probably the least useful in IR characterization of a compound?

A)phenol: 3500 cm^-1
B)alcohol: 3500 cm^-1
C)phenol: 1500-1600 cm^-1
D)ether: 1050-1150 cm^-1
E)all of these are about equally useful

Question 11

The following IR spectrum would most likely be associated with

Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-01-08)

A)phenol
B)aromatic alcohol
C)aliphatic alcohol
D)ether
E)cannot determine from the isolated spectrum

Question 12

Instructions: Provide correct IUPAC names for each of the structures below.

Name:

Question 13

What is the best choice of reagent to achieve the following transformation?

A)CrO₃,H₃O⁺,acetone
B)pyridium chlorochromate,CH₂Cl₂
C)SOCl₂,pyridine
D)NaBH₄,H₃O⁺
E)LiAlH₄,H₃O⁺

Question 14

Instructions: Provide correct IUPAC names for each of the structures below.

Name:

Question 15

What is the IUPAC name of the following compound?

A)ethyl isopropyl thiol
B)2-methylsulfanylpropane
C)ethyl isopropyl disulfide
D)ethyl isopropyl sulfide

Question 16

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

A)tert-butyl phenyl ether
B)isopropyl methyl ether
C)anisole
D)tert-butyl methyl ether

Question 17

What is the IUPAC name of the following compound?

A)cis-4-methylcyclohexanol
B)trans-4-methylcyclohexanol
C)cis-4-hydroxy-1-methylcyclohexane
D)trans-4-hydroxy-1-methylcyclohexane

Question 18

Which of the following would not react with either Na₂Cr₂O₇ or pyridinium chlorochromate?

A)only 1
B)only 3
C)only 2 and 4
D)1,2,3 and 4

Question 19

Instructions: To answer the following question(s),consider the reaction below.
Refer to instructions.Provide the IUPAC name for the product alcohol.