Organic Chemistry II

Recitation Problem Set #1

A Brief Review of CH235

Complete the reaction equations and indicate stereochemistry if relevant.

1. BH3
2. H2O2, OH1. Hg(OAc)2, H2O
2. NaBH4
NBS, H2O

HBr

Br2

Br2 / light

H2, Pd/C

KMnO4, H3O+

1. O3
2. Zn, H+

CHCl3, KOH

Br2 (excess)

Lindlar catalyst, H2

H3C C C CH3

1. BH3
2. H2O2, OH-

O3

Li/NH3

Draw resonance structures. Show electron pushing with curved arrow. Label any non-zero formal charges:
H

Provide the structures of the products in the following reaction sequences. Also provide the IUPAC name for
the molecules indicated and show stereochemistry when relevant.
HBr

IUPAC:

IUPAC:

IUPAC:

H2O (nucleophile)

H2O (nucleophile)

Show how to complete the following conversions, starting from cyclohexene.

OH

Br

CN