Question 1: Consider the nucleophilic substitution reaction between 1-chloro-
3,3-dimethylpentane and the cyanide ion:
xa
+
ci
NC-
1-chloro-3,3-dimethylpentane
(a) Is the alkyl halide 1°, 2° or 3°?
(b) Will the nucleophilic substitution reaction be Sn1 or Sn2?
(c) Give the substitution mechanism showing all full and partial
positive and negative charges, electron movements using curved
arrows and any intermediates or transition states.
2

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