Question 1

Which of the following statements best describes the stereochemical outcome of an $$\mathrm{S_N2}$$ reaction at a chiral center?

Accepted Answer

The configuration at the chiral center is inverted.

Question 2

A student treats 1-bromobutane with $$\mathrm{NaSH} in$$ $$\mathrm{DMSO}. $$What is the major product?

Accepted Answer

Butanethiol ($$\mathrm{CH_3CH_2CH_2CH_2SH})$$

Question 3

Which set of reagents would convert 1-hexene to 1-hexanol with anti-Markovnikov selectivity?

Accepted Answer

1. $$\mathrm{BH_3$}$$; 2. $$\mathrm{H_2O_2}$$/–OH

Question 4

Which of the following best describes the product(s) when an epoxide is treated with $$\mathrm{MeOH}$$ and catalytic $$\mathrm{H_2SO_4}$$?

Accepted Answer

A trans-1-methoxy-2-hydroxy compound

Question 5

Which of the following carbocations is most stabilized by rearrangement?

Accepted Answer

A primary carbocation adjacent to a tertiary carbon

Question 6

A student wants to synthesize (2R,3S)-butane-2,3-diol from an alkene. Which reagent sequence would be most appropriate?

Accepted Answer

1. $$\mathrm{$$OsO_4$$}$$; 2. $$\mathrm{$$NaHSO_3$$}$$

Question 7

Which of the following best describes the product when 2-methyl-2-butene is treated with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

A racemic mixture of 2,3-dibromo-2-methylbutane

Question 8

Which of the following statements about the reaction of an epoxide with $$\mathrm{$$NaOCH_3$$}$$ followed by water is correct?

Accepted Answer

The nucleophile attacks the less substituted carbon of the epoxide.

Question 9

Which of the following is the correct order of carbocation stability?

Accepted Answer

Tertiary \u003e Secondary \u003e Primary \u003e Methyl

Question 10

A student performs the following sequence: 1. $$\mathrm{NaH}$$; 2. $$\mathrm{CH_3Br} on $$cyclohexanol. What is the major product?

Accepted Answer

Cyclohexyl methyl ether

Question 11

Which of the following best describes the stereochemical outcome when $$\mathrm{Br_2$} is $$added to (E)-2-butene?

Accepted Answer

A meso compound is formed.

Question 12

Which reagent would convert a primary alcohol to a primary bromide with inversion of configuration?

Accepted Answer

$$\mathrm{$$PBr_3$$}$$

Question 13

Which of the following is the correct sequence to convert 1-butyne to 2-butanol?

Accepted Answer

1. $$\mathrm{$$HgSO_4$$}$$, $$\mathrm{H_2SO_4}$$, $$\mathrm{H_2O}$$; 2. Reduction

Question 14

Which of the following best describes the product when (S)-1-methoxy-2-methylbutan-2-ol is treated with $$\mathrm{NaH}$$?

Accepted Answer

The alcohol is deprotonated to form an alkoxide.

Question 15

Which of the following is true about the reaction of an alkene with $$\mathrm{Br_2$} in $$water?

Accepted Answer

A bromohydrin is formed with anti addition.

Question 16

Which of the following best describes the product when 1,2-epoxycyclohexane is treated with $$\mathrm{H_3O^+}$$?

Accepted Answer

Trans-1,2-cyclohexanediol

Question 17

Which of the following is the correct product when 1-butyne is treated with 1. $$\mathrm{$$NaNH_2$$}$$; 2. $$\mathrm{CH_3CH_2Br}$$?

Accepted Answer

1-hexyne

Question 18

Which of the following best describes the stereochemical outcome when (Z)-2-butene is treated with $$\mathrm{Br_2$}$$?

Accepted Answer

A racemic mixture of enantiomers is formed.

Question 19

Which of the following is the best method to synthesize an ether from a primary alcohol?

Accepted Answer

Williamson ether synthesis: 1. $$\mathrm{NaH}$$; 2. $$\mathrm{RBr}$$

Organic Chemistry Exam 3 Study Guidance

Study Guide - Practice Questions