Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 9, Problem 9.44P
Interpretation Introduction
Interpretation:
The increasing order of ratio of E2 to
Concept Introduction:
E2 reaction:
The elimination of leaving groups simultaneously is known as E2 elimination. In E2 reaction, more stable
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Elimination of HBr from 2-bromobutane affords a mixture of but-1-ene and but-2-ene. With sodium ethoxide as base, but2-ene constitutes 81% of the alkene products, but with potassium tert-butoxide, but-2-ene constitutes only 67% of the alkene products. Offer an explanation for this difference.
Compounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane.
Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene.
Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X.
What is the structure of X?
• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
.
Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
на
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reaction between 3-chloro-3-methyl-1-
butene with sodium acetate (CH3COO – Na +)
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Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 9.1PCh. 9.3 - Prob. 9.2PCh. 9.3 - Prob. 9.3PCh. 9.3 - Prob. 9.4PCh. 9.4 - Prob. 9.5PCh. 9.5 - Predict the -elimination product(s) formed when...Ch. 9.7 - Prob. 9.7PCh. 9.9 - Predict whether each reaction proceeds...Ch. 9.9 - Prob. AQCh. 9.9 - Prob. BQ
Ch. 9.9 - Prob. CQCh. 9.9 - Prob. DQCh. 9.10 - Prob. 9.9PCh. 9 - Prob. 9.10PCh. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Treatment of 1-aminoadamantane, C10H17N, with...Ch. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Attempts to prepare optically active iodides by...Ch. 9 - Draw a structural formula for the product of each...Ch. 9 - Prob. 9.23PCh. 9 - Alkenyl halides such as vinyl bromide, CH2=CHBr,...Ch. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Show how you might synthesize the following...Ch. 9 - Prob. 9.29PCh. 9 - 1-Chloro-2-butene undergoes hydrolysis in warm...Ch. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Solvolysis of the following bicyclic compound in...Ch. 9 - Which compound in each set undergoes more rapid...Ch. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Draw structural formulas for the alkene(s) formed...Ch. 9 - Prob. 9.38PCh. 9 - Following are diastereomers (A) and (B) of...Ch. 9 - Prob. 9.40PCh. 9 - Elimination of HBr from 2-bromonorbornane gives...Ch. 9 - Which isomer of 1-bromo-3-isopropylcyclohexane...Ch. 9 - Prob. 9.43PCh. 9 - Prob. 9.44PCh. 9 - Draw a structural formula for the major organic...Ch. 9 - When cis-4-chlorocyclohexanol is treated with...Ch. 9 - Prob. 9.47PCh. 9 - The Williamson ether synthesis involves treatment...Ch. 9 - The following ethers can, in principle, be...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 9 - Prob. 9.52PCh. 9 - Prob. 9.53PCh. 9 - Prob. 9.54PCh. 9 - Write the products of the following sequences of...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.59PCh. 9 - Another important pattern in organic synthesis is...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - Prob. 9.64P
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