Chemistry 331 - Winter 1996
Elements of Organic Chemistry I


Homework, Chapter 7 - Alkyl Halides

McMurry, pp 228 - 231:

Problems 7.24, 26-32, 34-39, 42, 48-52, 54, 55

See the Study Guide for answers for the problems from the text.



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.