Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 21, Problem 21.63P
Interpretation Introduction

Interpretation:

The reagent has to be given for the conversion of A to Tamoxifen.

Concept introduction:

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.63P , additional homework tip  1

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.63P , additional homework tip  2

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (H+) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.63P , additional homework tip  3

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction. Dehydration reaction will not go without acid (sulfuric acid).

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Chapter 21 Solutions

Organic Chemistry, Loose-leaf Version

Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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