H 1. BH3 2. H₂O2, NaOH 3. PCC 4. CH3MgBr 5. H3O+ workup Na₂Cr₂O7 H₂SO4, H₂O

Chemistry: The Molecular Science
5th Edition
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:John W. Moore, Conrad L. Stanitski
Chapter19: The Chemistry Of The Main-group Elements
Section: Chapter Questions
Problem 46QRT
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(a)
(c) HO
OH
1. BH3
2. H₂O₂, NaOH
3. PCC
4. CH3MgBr
5. H3O+ workup
Na₂Cr₂O7
H₂SO4, H₂O
Transcribed Image Text:(a) (c) HO OH 1. BH3 2. H₂O₂, NaOH 3. PCC 4. CH3MgBr 5. H3O+ workup Na₂Cr₂O7 H₂SO4, H₂O
Expert Solution
Step 1

(a) The alkene gives a hydroboration reaction and forms alcohol according to the anti-Markovnikov rule. The alkene is oxidized into aldehyde by PCC, and finally the aldehyde reacts with the Grignard reagent to form a secondary alcohol.

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