ORGANIC CHEMISTRY  LL PRINT UPGRADE
ORGANIC CHEMISTRY LL PRINT UPGRADE
4th Edition
ISBN: 9781119810643
Author: Klein
Publisher: WILEY
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Chapter 4, Problem 54PP
Interpretation Introduction

Interpretation:

Chair conformations of glucose should be drawn and most stable conformer is needed to be predicted between them.

Concept introduction:

Chair conformer: chair conformer is a stable conformer for cyclohexane compound. In this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.

Example:

ORGANIC CHEMISTRY  LL PRINT UPGRADE, Chapter 4, Problem 54PP

After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.

Stereochemistry conversions in chair conformation are shown below.

Substituent position cis trans
1,2 position (a,e) or (e,a) (a,a) or (e,e)
1,3 position (a,a) or (e,e) (a,e) or (e,a)
1,4 position (a,e) or (e,a) (a,a) or (e,e)

To find: chair conformers of glucose molecule and stable one between conformers.

Given compound is glucose.

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22.22 For each compound, indicate which group on the ring is more strongly activating and then draw a structural formula of the major product formed by nitration of the compound. Br CHO (a) CH3 (b) (c) CHO CH3 SO₂H (d) ☑ OCHS NO₂ (e) (f) CO₂H NHCOCH3 NHCOCH, (h) CHS 22.23 The following molecules each contain two aromatic rings. (b) 000-100- H3C (a) (c) Which ring in each undergoes electrophilic aromatic substitution more readily? Draw the major product formed on nitration.
V Consider this step in a radical reaction: Br: ? What type of step is this? Check all that apply. Draw the products of the step on the right-hand side of the drawing area below. If more than one set of products is possible, draw any set. Also, draw the mechanism arrows on the left-hand side of the drawing area to show how this happens. ⚫ionization termination initialization neutralization none of the abc Explanation Check 80 Ο F3 F1 F2 2 F4 01 % do5 $ 94 #3 X 5 C MacBook Air 25 F5 F6 66 ©2025 ˇ F7 29 & 7 8
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