Organic Chemistry 302

Examination Two-March 17, 1999

I. (Five points each) Synthesize the following:

a. 2,3-dimethyl-2-butanol from 2-butanol and anything else

II. (Three points each) Complete the following reactions:

a. t-butyl alcohol + KmnO₄ ®

b. methyl ethyl ether + CH₃-MgBr ®

c. ethanol + KMn0₄ ®

d. R-2-pentanol + PCl₃ ®

e. t-butyl alcohol + Na ®

f. cyclopentene + cold KMnO₄ ®

g. 1-pentanol + Cr0₃ ®

h. 1-methylcyclopentene + B₂H₆ ®

i. 3-methyl-1-pentene + ? ® 3-methyl-2-pentanol

j. cyclopentene + CH₃-C0₃H ®

k. 3,3-dimethylcyclopentene + H⁺ ®

III. (Four points each)

a. Would the following compound be expected to have a high boiling point? Explain.

b. Alcohols can be prepared from carbonyl containing compounds. Briefly explain which general types of alcohols can and cannot be prepared in this manner.

c. If the following ether were treated with HCl, which mechanism would it be most liekly to react by, SN₁ or SN₂? Explain.

IV. (Fifteen points) Consider the following compound:

Compound A (C₈H₁₆O

A + Br₂/CCl₄ ® n.r.

A + KmnO₄ ® n.r.

A + ZnCl₂/HCl ® immediate cloudy

A + H₂/cat ® n.r.

A + H⁺ ® B + C + D

(major) (middle) (minor)

B + H₂O/H⁺ ® A

B + Hg(OAc)₂/H₂O then NaBH₄ ® A

B + B₂H₆ then H₂O₂ ® A

C + H₂O/H⁺ ® A

C + Hg(OAc)₂/H₂O then NaBH₄ ® A

C + B₂H₆ then H₂O₂ ® L

D + H₂O/H⁺ ® A

D + HgOAc)₂/H₂O then NaBH₄ ® A

D + B₂H₆ then H₂O₂ ® E

E + KMnO₄ ® brown ppt.

E + ZnCl₂/HCl ® n.r.

B + O₃/Zn,H⁺ ® F

B + O₃/H₂O₂ ® F

C + O₃/Zn,H⁺ ® G

C + O₃.H₂O₂ ® H

D + O₃/Zn,H⁺ ® I + J

D + O₃/H₂O₂ ® I + K

Draw the structures of A through L.