Wrong Answers from ACS review on alcohol, diols, thiols

Question 1

Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH4 in methanol?

A. 1-Butanol

B. 2-Butanol

C. 2-methyl-1-propanol

D. 2-methyl-2-propanol

Answer 1

D. 2-methyl-2-propanol

Question 2

An alcohol has the same oxidation state as a(n):

A. Ketone

B. Alkene

C. Organolithium compound

D. Alkyl halide

Answer 2

D. Alkyl Halide

Question 3

Which one of the following diols would cleave into two fragments with HIO4?

A. 1,3-hexandiol

B. 2,4-hexanediol

C. 3,4-hexanediol

D. 1,6-hexanediol

Answer 3

C. 3,4- hexanediol

Question 4

Consider the structure of the AlH4^- ion. The formal charge of Al is:

A. -1

B. 0

C. +1

D. +3

Answer 4

A. -1

Question 5

As a reducing agent, NaBH4 donates a _________ to a ketone or aldehyde

A. Proton

B. Hydrogen atom

C. Hydride ion

D. Hydrogen molecule

Answer 5

C. Hydride ion

Question 6

What is the product of the reaction below?

A. CH3C=OCH2CH2CH3

B. CH3C=OOCH2CH2CH3

C. CH3CH(OH)OCH2CH2CH3

D. CH3CH2C=OOCH2CH3

Answer 6

B. CH3C=OOCH2CH2CH3

Question 7

The alcohol product(s) of the reduction of 2-methyl-3-pentanene with LIAlH4 is (are):

A. A single enantiomer

B. A racemic mixture

C. Two diastereomers

D. Two constitutional isomers

Answer 7

B. A racemic mixture

Question 8

What is the product of the following reaction sequence?

Answer 8

D is the answer