Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 7, Problem 32P
Interpretation Introduction

Interpretation:

The transition state leading to the conversion of 2-bromo-2-methylbutane into 2-methyl-2-butene on reaction with sodium ethoxide is to be written.

Concept introduction:

Sodium ethoxide is a reagent, which is widely used in reactions. It abstracts the most acidic proton from the reactant molecule.

Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.

Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Nucleophilic substitution reaction is a reaction in which an electron-rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

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Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.
Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.
When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%

Chapter 7 Solutions

Organic Chemistry

Ch. 7 - Practice Problem 7.11 (a) When...Ch. 7 - Prob. 12PPCh. 7 - Prob. 13PPCh. 7 - Practice Problem 7.14 Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15 Rank the following alcohols...Ch. 7 - Practice Problem 7.16 Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 18PPCh. 7 - Prob. 19PPCh. 7 - Practice Problem 7.20 Show how you might...Ch. 7 - Prob. 21PPCh. 7 - Prob. 22PPCh. 7 - Practice Problem 7.23 Write the structure of...Ch. 7 - Prob. 24PPCh. 7 - Prob. 25PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.36. Explain the following observations: When...Ch. 7 - Prob. 37PCh. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 39PPCh. 7 - Prob. 40PPCh. 7 - Prob. 41PPCh. 7 - Prob. 42PPCh. 7 - Your task is to prepare isopropyl methyl ether by...Ch. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Prob. 48PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 53PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - cis-4-Bromocyclohexanol tBuOHtBuO racemic C6H10O...Ch. 7 - Prob. 59PPCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 61PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGP
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