Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 8, Problem 33CTQ
Interpretation Introduction

Interpretation: Number of synthetic steps below reaction should be stated.

  Organic Chemistry: A Guided Inquiry, Chapter 8, Problem 33CTQ

Concept introduction: The carbon-carbon double bond in alkene consists of a strong σ bond (formed by overlap of sp2 hybridized orbital on each carbon) and a weak π bond (formed by overlap of pure p orbital on each carbon). Due to unsaturation, alkene shows addition reaction where the double bond provides loosely held π electrons and is readily attacked by any electron deficient group like H+ ions released from acids. The loosely held π electrons are present, therefore, behave as base though weak one.

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OTS OTS 4) Consider the two E2 reactions above. KOtBu DMF heat KOtBu DMF heat a. What are the major products for each reaction? b. What is the mechanism for each reaction? c. Which reaction would be faster and why? Use words like "transition-state, intermediate and/or reactant/product stability" in your justification. Draw the reaction coordinate diagram for both to assist in your explanation.
In case of dihalide like problem 8.54 c.  1. my think is like this. at the first E2 reaction, the hydrogen on cyclohexyl will be participate because its carbon is more substituted.  then second E2 reaction, there are no more hydrogen on left carbon. so hydrogen on right carbon will be partcipate. as a result, the product is double bond not triple bond. Why is this wrong and only form triple bond? 2. Is it impossible to make Sn2 reaction that NH2- is working as nucleophile?
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Organic Chemistry: A Guided Inquiry

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Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning