Question 1

Which reagent would you use to selectively reduce an alkyne to a trans-alkene?

Accepted Answer

Na, NH\_3 (liq)

Question 2

What is the major product when 1-hexene is treated with mCPBA?

Accepted Answer

1,2-epoxyhexane

Question 3

A cyclohexanol is oxidized with PCC. What is the expected product?

Accepted Answer

Cyclohexanone

Question 4

Which of the following best describes the product of the reaction: $$\mathrm{CH_3CH_2CH_2CH_2OH} + $$PCC?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CHO}$$

Question 5

Which reagent would convert a primary alcohol to a carboxylic acid?

Accepted Answer

Na\_2Cr\_2O\_7, H\_2SO\_4, H\_2O

Question 6

What is the product when 1-butyne is treated with Na, NH\_3 (liq)?

Accepted Answer

trans-2-butene

Question 7

Which of the following is the correct sequence of reagents to convert 1-hexene to 1,2-hexanediol?

Accepted Answer

mCPBA, then H\_3O^+

Question 8

A compound with molecular formula C\_4H\_8 produces an epoxide when treated with mCPBA. Which structure is most likely?

Accepted Answer

1-butene

Question 9

Which of the following reactions will convert cyclohexene to cyclohexane?

Accepted Answer

H\_2, Pd/C

Question 10

What is the expected product when 1-hexanol is treated with Na\_2Cr\_2O\_7, H\_2SO\_4, H\_2O?

Accepted Answer

Hexanoic acid

Question 11

Which reagent would you use to convert a ketone to a secondary alcohol?

Accepted Answer

LiAlH\_4, H\_2O

Question 12

What is the product of the reaction: cyclohexene + mCPBA?

Accepted Answer

Cyclohexene oxide

Question 13

Which of the following best describes the product of ozonolysis of 1-hexene followed by reduction with Zn/H\_2O?

Accepted Answer

Hexanal and formaldehyde

Question 14

Which reagent would you use to convert an alkene to a vicinal diol?

Accepted Answer

OsO\_4, H\_2O\_2

Question 15

What is the major product when 2-pentyne is treated with H\_2, Lindlar's catalyst?

Accepted Answer

cis-2-pentene

Question 16

Which of the following is a correct mechanism for the formation of an epoxide from an alkene using mCPBA?

Accepted Answer

Concerted electrophilic addition forming a three-membered ring

Question 17

A student wants to convert 1-butyne to cis-2-butene. Which reagent should they use?

Accepted Answer

H\_2, Lindlar's catalyst

Question 18

Which of the following reagents would oxidize a secondary alcohol to a ketone?

Accepted Answer

PCC

Question 19

What is the expected product when cyclohexanone is treated with LiAlH\_4 followed by H\_2O?

Accepted Answer

Cyclohexanol

Question 20

Which of the following best describes the product of the reaction: 1-hexene + OsO\_4, H\_2O\_2?

Accepted Answer

1,2-hexanediol

Alcohols, Ethers, Epoxides, and Thiols: Reactions and Synthesis (Chapter 12 Study Guide)

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