ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Chapter 15.5, Problem 15.7P

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

  1. a. 3 — methylbut — 2 — en — 1 — ol -+- HBr→1 — bromo — 3 — methylbut — 2 — ene + 3 — bromo — 3 — methylbut — 1 — ene
  2. b. 2 — methylbut — 3 — en — 2 — ol + HBr → 1 — bromo — 3 — methylbut — 2 — ene + 3 — bromo — 3 — methylbut — 1 — ene
  3. c. cyclopenta-1,3-diene + Br2 →3,4-dibromocyclopent-1-ene + 3,5-dibromocyclopent-1-ene
  4. d. 1 — chlorobut — 2 — ene + AgNO3, H2O→but — 2 — en — 1 — ol + but — 3 — en — 2 — ol
  5. e. 3 — chlorobut — 1 — ene + AgNO3, H2O→but — 2 — en — 1 — ol + but — 3 — en — 2 — ol
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