H Benzaldehyde Br. bromoaldehyde 1. Mg, ether + Br. 4-Bromobutanal H OH H 5-Hydroxy-5-phenylpentanal (racemic) OH H+ Br. H + HO diol Q-MgBr+ HCl, H₂O A cyclic acetal +H.O OH H OH + HO 2. C6H5CHO A chiral magnesium alkoxide (produced as a racemic mixture) 5-Hydroxy-5-phenylpentanal (formed as a racemic mixture)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 62GP: The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a...
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Illustrate the mechanism or synthesis for the following reaction. Show all steps.

H
Benzaldehyde
Br.
bromoaldehyde
1. Mg, ether
+
Br.
4-Bromobutanal
H
OH
H
5-Hydroxy-5-phenylpentanal
(racemic)
OH
H+
Br.
H
+
HO
diol
Q-MgBr+
HCl, H₂O
A cyclic acetal
+H.O
OH
H
OH
+ HO
2. C6H5CHO
A chiral magnesium alkoxide
(produced as a racemic mixture)
5-Hydroxy-5-phenylpentanal
(formed as a racemic mixture)
Transcribed Image Text:H Benzaldehyde Br. bromoaldehyde 1. Mg, ether + Br. 4-Bromobutanal H OH H 5-Hydroxy-5-phenylpentanal (racemic) OH H+ Br. H + HO diol Q-MgBr+ HCl, H₂O A cyclic acetal +H.O OH H OH + HO 2. C6H5CHO A chiral magnesium alkoxide (produced as a racemic mixture) 5-Hydroxy-5-phenylpentanal (formed as a racemic mixture)
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