23. In the three-step synthesis below, at least one of the steps would fail as shown. For each step, indicate whether each step would succeed or fail by circling the proper answer. If a step would fail briefly describe why and how you would rectify the synthesis.

23. In the three-step synthesis below, at least one of the steps would fail as shown. For each step, indicate whether each step would succeed or fail by circling the proper answer. If a step would fail briefly describe why and how you would rectify the synthesis.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 11E

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Question

Question #23.

23. In the three-step synthesis below, at least one of the steps would fail as shown. For each
step, indicate whether each step would succeed or fail by circling the proper answer. If a
step would fail briefly describe why and how you would rectify the synthesis.
OH
would this stop
Succeed or Fail
1. CH MgBr (1 Equiv.)
2. H₂O* (workup)
(circle one)
OH
Na₂Cr₂O7
H₂SO4
OH
1. SOCI₂
2. Mg(s), Et₂O
3.
Å
4. H₂O* (workup)
OH
H₂C
Succeed or Fail
(circle one)
H₂C
Succeed or Fail
(circle one)
H3C
OH
(converts -OH to -CI)

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