Question 1

Which of the following reagents would you use to synthesize cyclohexene from cyclohexanol?

Accepted Answer

$$\mathrm{H_2SO_4}$$, heat

Question 2

What is the major product when 2-bromobutane is treated with $$\mathrm{KOH} in $$ethanol?

Accepted Answer

2-butene (cis and trans mixture)

Question 3

Which of the following best describes the mechanism of dehydrohalogenation of alkyl halides?

Accepted Answer

E2 elimination

Question 4

When 1,2-dibromocyclohexane is treated with $$\mathrm{$$NaNH_2$$} in $$liquid ammonia, what is the product?

Accepted Answer

Cyclohexyne

Question 5

Which reagent would you use to convert an alkyne to a cis-alkene?

Accepted Answer

$$\mathrm{H_2$}$$, Lindlar's catalyst

Question 6

What is the expected product when 1-butene reacts with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

1,2-dibromobutane

Question 7

Which of the following statements about Markovnikov's rule is correct?

Accepted Answer

The hydrogen atom adds to the carbon with the most hydrogens already attached.

Question 8

Which of the following reactions will produce an anti addition product?

Accepted Answer

Addition of $$\mathrm{Br_2$} to $$cyclohexene

Question 9

What is the product of oxidative cleavage of 1,2-dimethylcyclohexene with $$\mathrm{O_3$}$$ followed by $$\mathrm{Zn, H_2O}$$?

Accepted Answer

Two ketones

Question 10

Which of the following is a correct statement about the reduction of alkynes with sodium in liquid ammonia?

Accepted Answer

It produces a trans-alkene

Question 11

Which reagent would you use to convert 1-butyne to 2-butanone?

Accepted Answer

$$\mathrm{$$HgSO_4$$}$$, $$\mathrm{H_2SO_4}$$, $$\mathrm{H_2O}$$

Question 12

Which of the following best describes the product of hydroboration-oxidation of 1-hexene?

Accepted Answer

Hexan-1-ol (anti-Markovnikov alcohol)

Question 13

Which of the following is the correct product when cyclohexene is treated with $$\mathrm{$$KMnO_4$$} ($$cold, dilute)?

Accepted Answer

cis-1,2-cyclohexanediol

Question 14

Which of the following reactions is used to synthesize alkynes from vicinal dihalides?

Accepted Answer

Dehydrohalogenation with $$\mathrm{$$NaNH_2$$}$$

Question 15

Which of the following is the major product when 2-methyl-2-butene reacts with $$\mathrm{HBr} in $$the presence of peroxides?

Accepted Answer

1-bromo-2-methylbutane

Question 16

Which of the following is true about the polymerization of ethylene?

Accepted Answer

It produces polyethylene

Question 17

Which of the following reagents would you use for syn dihydroxylation of an alkene?

Accepted Answer

$$\mathrm{$$OsO_4$$}$$, $$\mathrm{H_2O_2}$$

Question 18

Which of the following is the product of hydration of 1-pentyne using $$\mathrm{$$HgSO_4$$}$$ and $$\mathrm{H_2SO_4}$$?

Accepted Answer

2-pentanone

Question 19

Which of the following best describes the stereochemistry of the product formed when cyclohexene reacts with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

Anti addition

Question 20

Which of the following is the correct product when 1-hexyne is treated with $$\mathrm{BH_3$}$$ followed by $$\mathrm{H_2O_2}$$ and $$\mathrm{OH^-}$$?

Accepted Answer

Hexanal

Synthesis and Reactions of Alkenes and Alkynes

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