Question 1

Which set of reagents would accomplish the transformation of methylcyclohexene to trans-2-methylcyclohexanol as shown in the first image?

Accepted Answer

E) 1) $$\mathrm{BH_3$/THF} 2$$) $$\mathrm{HO^-}$$, $$\mathrm{H_2O_2}$$, $$\mathrm{H_2O}$$

Question 2

When cyclohexene reacts with $$\mathrm{Br_2$/$$CCl_4$$}$$, which intermediate and product are formed as shown in the second image?

Accepted Answer

D) IV & V

Question 3

What is the major product when excess $$\mathrm{HBr} is $$added to 1-hexyne?

Accepted Answer

E) 2,2-dibromohexane

Question 4

How many distinct alkynes exist with a molecular formula of $$\mathrm{C_4H_6}$$?

Accepted Answer

D) 3

Question 5

Which statement is true regarding the hydroboration-oxidation of an alkene?

Accepted Answer

C) Anti-Markovnikov orientation and syn addition occur.

Question 6

What is the name of the product formed when an alkene reacts with a peracid, resulting in a three-membered ring containing oxygen?

Accepted Answer

D) epoxide

Question 7

Which reagent is needed to convert 2-butyne to cis-2-butene, as shown in the third image?

Accepted Answer

B) $$\mathrm{H_2$/Lindlar's\ catalyst}$$

Question 8

How many distinct products will be obtained in the ozonolysis of the compound shown in the fourth image?

Accepted Answer

C) 3

Question 9

Dissolving metal reduction involves which of the following?

Accepted Answer

B) Addition of $$\mathrm{H_2$} to a $$triple bond in the presence of Na in liquid $$\mathrm{NH_3$}$$

Question 10

Which intermediate is thought to occur in the mechanism by which alkenes are hydrated in the presence of acid?

Accepted Answer

B) carbocation

Question 11

Provide the reagents necessary to convert an alkene to an alcohol via anti-Markovnikov addition.

Accepted Answer

A) 1. $$\mathrm{BH_3$\cdot THF} 2$$. $$\mathrm{H_2O_2, HO^-}$$

Question 12

Keto-enol forms are best described as:

Accepted Answer

D) constitutional isomers

Question 13

Starting with 2-butene, which method is best for preparing 2-butyne?

Accepted Answer

D) $$\mathrm{Br_2$/$$CCl_4$$}$$; $$\mathrm{2NaNH_2}$$

Question 14

Which of the following is NOT a nucleophile?

Accepted Answer

A) $$\mathrm{$$FeBr_3$$}$$

Question 15

Which of the following reagents will accomplish the reduction of an alkyne to a trans-alkene, as shown in the fifth image?

Accepted Answer

E) $$\mathrm{Na / Liq. NH_3$}$$

Question 16

What is the correct IUPAC name for the compound shown in the sixth image?

Accepted Answer

D) (E) 1-cyclopentyl-3,6-dimethylhept-3-en-1-yne

Question 17

Which of the following improperly describes the physical properties of an alkyne?

Accepted Answer

D) insoluble in most organic solvents

Question 18

What is the product for the reaction of 1-butene with methanol in the presence of acid?

Accepted Answer

D) 2-methoxybutane

Question 19

Which of the following is the final and major product of the hydration of phenylacetylene with $$\mathrm{H_2SO_4}$$ and $$\mathrm{$$HgSO_4$$}$$, as shown in the seventh image?

Accepted Answer

A) I

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