Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 6.2, Problem 6.3TIY

(a)

Interpretation Introduction

Interpretation:The starting materials to produce (CH3CH2)2O should be suggested.

Concept introduction: (CH3CH2)2O is an ether having two similar CH3CH2 alkyl groups.

(b)

Interpretation Introduction

Interpretation: The starting materials to produce (CH3)4N+I should be suggested.

Concept introduction: (CH3)4N+I is a derivative of NH4+ where the four Hydrogen atoms have been replaced with four CH3 alkyl groups.

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(b) (d) (b) The following reactions as written will NOT give the indicated product. For each of the reactions explain (a) НО (i) (ii) (iii) OH The reason why the reaction as written will not occur; How the reaction could be modified to give the indicated product (may include the use of alternative or additional reagents); What should be the outcome for the reactions as written? OH CO,CH,CH, OH 1. CH₂OH/H* 2. Zn/Hg 3. H* 1, (CH₂CH₂)CuLi 2. PCC CrO3 Pyridine 2 x CH₂MgBr H+ ỌCH3 COH(CH3)2 = OH
b) i) ii) iii) Consider the following reaction scheme to answer questions (i) to (iii) Br Mg Ether MgBr Product 2 was never obtained from the reaction shown above, provide a brief explanation as to why this reaction didn't work. Give the structure(s) of the compound that will form under these conditions. The researchers then decided to change the starting material and reaction conditions, to those shown below, and were able to obtain product 2 in 98% yield. Provide a detailed mechanism on how reactants 3 and 4 lead to the formation of product 2.
Consider the following structural formulas. OH -осн A в D E (a) Which of the compounds A-E can easily be oxidized? (b) Provide the typical oxidation products for all compounds selected in (a). (c) Explain why the compounds not selected in (a) cannot be easily oxidized.
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