H,SO, BHT (C,3H2,0) 2-methylprop-1-ene (2 equiv) p-cresol

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.5: Cyclic Structures Of Monosaccharides: Anomers
Problem 14P
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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 (C,3H2,0)
2-methylprop-1-ene
(2 equiv)
p-cresol
Transcribed Image Text:H,SO, BHT (C,3H2,0) 2-methylprop-1-ene (2 equiv) p-cresol
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