Question

1. Which of the following are possible products when t-butyl bromide is heated in aqueous acetone? Mark ALL that apply

A. t-butanol

B. 1-methylpropene

C. 2-methylpropene

D. 2-methyl-1-propanol

2. Which of the following is the major product when 2-bromo-3-methylbutane is treated with ethanolic potassium hydroxide?

A. 3-methyl-1-butene

B. 2-methyl-1-butene

C. 1-methyl-2-butene

D. 2-methyl-2-butene

3. Which of the following is the major product when 1-iodobutane is treated with sodium hydroxide in dimethylsulfoxide?

A. 1-butene

B. 1-butanol

C. 2-butene

D. 2-butanol

4. Which of the following is the major product when 3,3-dimethyl-2-butanol is refluxed in the presence of phosphoric acid?

A. 2,3-dimethyl-2-butene

B. 3,3-dimethyl-1-butene

C. 2-methyl-2-butene

D. 2,3-dimethyl-2-butanol

5. When benzyl bromide is relfuxed in ethanol the major product is ethyl benzyl ether. Which of the following statements are true regarding this process?

A - the first mechanistic step is ionization to produce a carbocation and bromide

B - the second mechanistic step is nucleophilic attack by a molecule of ethanol

C - The third mechanistic step is a proton transfer resulting in the final product

D- A and B only

E- A, B, and C

7. Rank the compounds below by acidity. (#1 = most acidic)

A. cyclohexanol

B. phenol     

C. acetic acid

D. 2,2-difluoro-1-cyclohexanol

8. Which of the following could be used to stoichiometrically produce the conjugate base of cyclohexanol? Mark ALL that apply.

A. Lithium hydride in THF

B. sodium metal in THF

C. potassium hydroxide in ethanol

D. liquid ammonia

9. Which of the following would produce 1-ethylcyclohexene as the major product when starting with 1-ethylcyclohexanol? Mark ALL that apply.

A. 1. TsCl/py 2. NaOH

B. phosphoryl chloride in pyridine

C. reflux in sulfuric acid

D. sodium hydride in THF

10. Which of the following will produce an optically active alkyl halide as the major product? Mark ALL that apply.

A. Reaction of (R)-2-butanol with thionly chloride in ether

B. Reaction of (S)-3-hexanol with phosphorous tribromide in ether

C. Reaction of t-butanol with thionyl chloride in ether

D. Reaction of (S)-2-butanol with hydroiodic acid in water

12. Which of the following alkyl halides would be the most reactive towards phenoxide in the Williamson ether synthesis?

A. t-butyl bromide

B. 1-bromopropane

C. 2-iodopropane

D. methyl iodide

14. Which of the following reagents or sequences of reagents could be used to transform 1-iodopentane into 1-pentanethiol? Mark ALL that apply.

A. sodium sulfide in DMF

B. thiourea followed by aqueous potassium hydroxide

C. NaSMe in DMSO

D. aqueous sodium hydroxide followed by thiourea

15. Which of the following could be used to make DMSO from dimethylsulfide? Mark ALL that apply.

A. sodium periodate

B. 1 equivalent of hydrogen peroxide

C. two equivalents of hydrogen peroxide

D. excess hydrogen peroxide

E. peroxy acetic acid

Answer 1