Pearson eText Organic Chemistry -- Instant Access (Pearson+)
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
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Chapter 20, Problem 53P
Interpretation Introduction

Interpretation:

The Daldopentose given in the sequence of reactions has to be identified.

Concept Introduction:

The Wohl degradation is the opposite of Kiliani Fischer synthesis which decreases the aldose chain by one carbon atom that is hexoses having ix carbons are converted to pentoses having five carbon and pentoses having five carbons are converted to tetroses having four carbons.

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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.
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Chapter 20 Solutions

Pearson eText Organic Chemistry -- Instant Access (Pearson+)

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