Introduction To General, Organic, And Biochemistry
Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 14, Problem 27P
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Interpretation Introduction

Interpretation: The chiral molecule/s needs to be identified from the three related angiotensin converting enzyme inhibitors. The number of stereoisomers possible needs to be identified for each chiral molecule. The three structures need to be compared with captopril and similarity among four drugs needs to be explained.

Concept Introduction:

A molecule is said to be chiral if it is non-superimposable with its mirror image. For example, left and right hands. These two non-superimposable mirror images of chiral molecules are known as enantiomers.

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assign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither.
12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?
Refer to the list of compounds shown below when answering questions 4(a) to 4(j) (a) A 50:50 mixture of structure VI with what other compound would lead to a racemic mixture?(b) Identify one compound that is identical to structure IV.  (c) Identify one compound that is identical to structure V.  (d) Identify one compound that is expected to have identical physical properties as structure II.  (e) Other than structures III and VI, identify a stereoisomer with a different boiling point from that of structure II.  (f) Other than structures IV, identify one diastereomer of structure I.  (g) How many stereoisomers may be derived from structure V?  (h) Specify the absolute (R/S) configuration of the amino group in structure IV. (i) If the substituents in structures I, IV and V were identical (all OH or all NH2), which structure would result in a meso compound?  (j) If each hydroxy group for structures I, II and VI were replaced with another amino group, which compound would be made optically…

Chapter 14 Solutions

Introduction To General, Organic, And Biochemistry

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