McMurry, pp 228 - 231:
Problems 7.24, 26-32, 34-39, 42, 48-52, 54, 55
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 with 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-).
2. Write out all of the possible isomers that could be formed from radical
chlorination (monochloro products) of (S)-3-methylheptane. Identify the
expected stereochemistry of each product.