ORGANIC CHEMISTRY  LL PRINT UPGRADE
ORGANIC CHEMISTRY LL PRINT UPGRADE
4th Edition
ISBN: 9781119810643
Author: Klein
Publisher: WILEY
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Chapter 13, Problem 47ASP
Interpretation Introduction

Interpretation: The possible intermediate formed in the given reaction needs to be identified.

Concept Introduction:

Epoxide reaction with alcohol under acidic conditions results in ring opening. It is an acid-catalyzed ring opening reaction. Alcohol act as a nucleophile in this case. Under acidic condition, first epoxide gets protonated and this protonated epoxide then reacts with alcohol to cause ring opening.

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You determine the bimolecular rate constant k for a set of SN2 reactions. Based on your understanding of how the nucleophile effects the rate constant for an SN2 reaction, drag and drop the nucleophiles into the correct rows in the table below. Alkyl halide Nucleophile k / L mol-1 s-1 CI 0.011 -CI 0.045 0.074 0.095 -NH2 -NH2 >-NH2 -NH2 -NH2
d) During the reaction between 3, 3-dimethylbutene (W) and HBr, intermediate species and Y are formed. CH3 CH;-C-CH=CH2 ČH3 HBr Y step 1 step 2 step 3 i) Write a mechanism for the formation of intermediate X? ii) Write the structure of intermediate Y? iii) Explain in your own words what happens in step 2 of the reaction? iv) Write a mechanism for the formation of Z from Y?
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