Answers to the Quiz

1.  B          In this question, the primary alkyl halide is treated with cyanide which is a good nucleophile.  Primary alkyl halides are not sterically hindered and are readily displaced in Sn2 reactions. Cyanide will displace the bromide to produce 5-methylheptanenitrile in good yield.

2.  B          An Sn1 reaction is a first order nucleophilic substitution reaction.  It is called first order because the rate limiting step involves only one molecule. 

3.  C          Sn2 reactions give the best results if a polar aprotic solvent is used.

4.  D          Since a tertiary haloalkane has been converted to an alkene, this is an elimination reaction.  This particular compound, 2-chloro-2-methylpropane, can react through either E1 or E2.  Since methoxide is a strong base, elimination occurs by E2 mechanism.

5.  B          A strong base favors E2.

6.  C          This reaction is Sn1 and in order to occur, there must be  a good leaving group and a strong incoming nucleophile.  In choice C, X is a tosylate ion, and excellent leaving group and Y is a cyanide, an excellent nucleophile. 

7.  B          Inversion of configuration is a trademark of the Sn2 reacion. 

8.  F           E2 reactions favor the formation of the more substituted double bonds

9.  T           Since both begin with the formation of a carbocation, they are influenced   by the same factors.