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Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 24, Problem 24.32SP
Suggest a method for the synthesis of the unnatural D enantiomer of alanine from the readily available I enantiomer of lactic acid.
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16. The proton NMR spectral information shown in this problem is for a compound with formula
CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec-
tral results, including DEPT-135 and DEPT-90 results, are tabulated:
7
J
Normal Carbon
DEPT-135
DEPT-90
19 ppm
Positive
No peak
122
Positive
Positive
cus
и
124
Positive
Positive
126
Positive
Positive
128
No peak
No peak
4°
129
Positive
Positive
130
Positive
Positive
(144
No peak
No peak
148
No peak
No peak
150
Positive
Positive
してし
3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing
mechanism below, but make sure to draw the product of each proposed step (3 points).
+ En
CN
CN
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Chapter 24 Solutions
Organic Chemistry (9th Edition)
Ch. 24.2A - Draw three-dimensional representations of the...Ch. 24.2A - Prob. 24.2PCh. 24.2B - The herbicide glyphosate (Roundup) kills plants by...Ch. 24.4 - Draw the structure of the predominant form of a....Ch. 24.4 - Draw the resonance forms of a protonated guanidino...Ch. 24.4 - Although tryptophan contains a heterocyclic amine,...Ch. 24.4 - Prob. 24.7PCh. 24.4 - Prob. 24.8PCh. 24.5A - Show how the following amino acids might be formed...Ch. 24.5B - Prob. 24.10P
Ch. 24.5C - Prob. 24.11PCh. 24.5C - Show how you would use a Strecker synthesis to...Ch. 24.6 - Suggest how you would separate the free i-ammo...Ch. 24.7A - Propose a mechanism for the acid-catalyzed...Ch. 24.7A - Give equations for the formation and...Ch. 24.7B - Prob. 24.16PCh. 24.7C - Prob. 24.17PCh. 24.8B - Draw the complete structures of the following...Ch. 24.9C - Prob. 24.19PCh. 24.9C - Prob. 24.20PCh. 24.9C - Prob. 24.21PCh. 24.9E - Prob. 24.22PCh. 24.9E - Prob. 24.23PCh. 24.10A - Propose a mechanism for the coupling of acetic...Ch. 24.10B - Show how you would synthesize Leu-Gly-Ala-Val-Phe...Ch. 24.10B - Show how solid-phase peptide synthesis would be...Ch. 24 - a. The isoelectric point (pl) of phenylalanine is...Ch. 24 - Prob. 24.28SPCh. 24 - Prob. 24.29SPCh. 24 - Prob. 24.30SPCh. 24 - Prob. 24.31SPCh. 24 - Suggest a method for the synthesis of the...Ch. 24 - Prob. 24.33SPCh. 24 - Write the complete structures for the following...Ch. 24 - The following structure is drawn in an...Ch. 24 - Prob. 24.36SPCh. 24 - Prob. 24.37SPCh. 24 - Show the steps and intermediates in the synthesis...Ch. 24 - Prob. 24.39SPCh. 24 - Lipoic acid is often found near the active sites...Ch. 24 - Prob. 24.41SPCh. 24 - Prob. 24.42SPCh. 24 - Prob. 24.43SPCh. 24 - Complete hydrolysis of an unknown basic...Ch. 24 - Prob. 24.45SPCh. 24 - Prob. 24.46SPCh. 24 - Prob. 24.47SP
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- Label the spectrum with spectroscopyarrow_forwardQ1: Draw the most stable and the least stable Newman projections about the C2-C3 bond for each of the following isomers (A-C). Are the barriers to rotation identical for enantiomers A and B? How about the diastereomers (A versus C or B versus C)? enantiomers H Br H Br (S) CH3 H3C (S) (R) CH3 H3C H Br A Br H C H Br H3C (R) B (R)CH3 H Br H Br H3C (R) (S) CH3 Br H D identicalarrow_forwardLabel the spectrumarrow_forward
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