H,SO, BHT (C15H240) p-cresol 2-methylprop-1-ene (2 equlv)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter3: Organic Compounds: Alkanes And Their Stereochemistry
Section3.SE: Something Extra
Problem 47AP: Draw the most stable conformation of 1,4-dichlorobutane, using wedges and dashes to represent bonds...
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Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords
BHT, a preservative with molecular formula C15H24O. BHT gives the
following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0
(singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT?
Draw a stepwise mechanism illustrating how it is formed.

H,SO,
BHT (C15H240)
p-cresol
2-methylprop-1-ene
(2 equlv)
Transcribed Image Text:H,SO, BHT (C15H240) p-cresol 2-methylprop-1-ene (2 equlv)
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