Chem 334 - Fall 1999
Organic Chemistry I
Dr. Carl C. Wamser

Chapter 8 Homework Answers

Brown & Foote, pages 313 - 321:
Problems 8.9 - 19, 21 - 24, 26 - 29, 31 - 34, 36 - 50

1. Consider the three constitutional isomers:

1-bromo-3-methylbutane
2-bromo-3-methylbutane
2-bromo-2-methylbutane

a) Select the isomer that will be most reactive in an SN2 reaction and illustrate its SN2 and E2 mechanisms when it reacts with sodium methoxide (NaOCH3).

b) Select the isomer that will be most reactive in an SN1 reaction and illustrate its SN1 and E1 mechanisms when it reacts in methanol (CH3OH).

c) Select an isomer that could be prepared in optically active form and show the stereochemistry of the SN2 reaction of the (R) enantiomer with azide anion (N3-).