H,SO4 OH BHT (C5H240) p-cresol 2-methylprop-1-ene (2 equiv)

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter7: Cycloalkanes
Section: Chapter Questions
Problem 15CTQ
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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,SO4
OH
BHT (C5H240)
p-cresol
2-methylprop-1-ene
(2 equiv)
Transcribed Image Text:H,SO4 OH BHT (C5H240) p-cresol 2-methylprop-1-ene (2 equiv)
Expert Solution
Step 1

Given:

Chemistry homework question answer, step 1, image 1

Step 2

The structure of BHT (butylated hydroxytoluene) is given below.

Chemistry homework question answer, step 2, image 1

The mechanism of the reaction is given below.

 

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