ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
4th Edition
ISBN: 9781119832638
Author: Klein
Publisher: WILEY
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Chapter 24.5, Problem 3LTS
Interpretation Introduction

Interpretation:

The more stable chair conformation of α-D-galactopyranose should be drawn.

Concept introduction:

  • Haworth projection is used to represent sugars in their cyclic forms.
  • In Haworth projection,
    • α-indicates the –OH group of anomeric carbon C1 and CH2OH substituent on the C5 carbon is trans to each other.
    • D indicates the CH2OH substituent on the C5 carbon is on up position.
    • The right side and left side –OH groups of chiral carbons in fisher projection are drawn as down side and upward side respectively.
  • Chair conformation is drawn according to the respective carbons in Haworth projection.
  • Stability of chair conformation is depending upon the positions of bulky substituents whether on axial or equatorial, the location of bulky substituents on equatorial position is more stable than bulky substituents on axial position.

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1. Show the steps necessary to make 2-methyl-4-nonene using a Wittig reaction. Start with triphenylphosphine and an alkyl halide. After that you may use any other organic or inorganic reagents. 2. Write in the product of this reaction: CH3 CH₂ (C6H5)₂CuLi H₂O+
3. Name this compound properly, including stereochemistry. H₂C H3C CH3 OH 4. Show the step(s) necessary to transform the compound on the left into the acid on the right. Bri CH2 5. Write in the product of this LiAlH4 Br H₂C OH
What are the major products of the following reaction? Please provide a detailed explanation and a drawing to show how the reaction proceeds.

Chapter 24 Solutions

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.

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