Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 26.5, Problem 9P
Interpretation Introduction
Interpretation:
The products of the given reactions typical of the
Concept Introduction:
Amino acids contain two functional groups, a
Amino acids therefore undergo reactions of carboxylate group as well as
They also undergo reactions typical of carbonyl group.
Depending on any functional group present in the side chain, they may also undergo other reactions characteristic of that group.
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There are 20 common, naturally occurring amino acids from which all proteins are derived (as will be discussed in Chapter 25),
although many other less common amino acids have been isolated from natural sources. Valine is one of the 20 common amino acids,
and it was used as a starting material in the laboratory synthesis of an uncommon amino acid (Tetrahedron 1997, 53, 1151-1156).
During one of the steps in the synthesis, compound 1 was treated with HBr under conditions that favor radical addition, giving
stereoisomers 2 and 3. Draw the structures of 2 and 3, and describe their stereoisomeric relationship.
H.
LOCH3
HBr
2 + 3
hv
H
(S)-valine
Modify the given copies of compound 1 to drawthe structures of 2 and 3. You can use the single bond tool to add/remove double
bonds.
CH2
CH2
H,C-
H3C-
-CH,
-CH,
Edit Drawing
Describe the relationship of 2 and 3.
O They are enantiomers.
O They are superimposable.
They are diastereomers.
O They are constitutional isomers.
a-Amino acids have the following general form:
H
H,N-C
R-group
a) Draw the structures of any amino acid (one for each of the following) with:
i.
A hydrophobic R-group-that contains a double bond
An acidic R-group
A basic R-group
ii.
ii.
The amine, carboxylic acid and R-group of an amino acid may be ionised under certain pH conditions.
b) For amino acids (i– i), draw their most probable structure in biological fluid, pH 7.4.
c) For amino acids (i– i), draw their most probable structure in stomach acid, pH 1.
-
Phenol plus 1) 1/2 I2, HNO3; 2) Br2 + AlCl3; 3) HNO3/H2SO4; can yield ___________.
2-bromo-6-iodo-4-nitrophenol
1-bromo-3-iodo-4-amino-phenol
3-bromo-5-iodo-4-nitrobenzene
2-bromo-3-iodo-4-hydroxy-aniline
2-bromo-3-iodo-4-nitrophenol
Chapter 26 Solutions
Organic Chemistry - Standalone book
Ch. 26.1 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Prob. 3PCh. 26.3 - Prob. 4PCh. 26.3 - Prob. 5PCh. 26.4 - Prob. 6PCh. 26.4 - Prob. 7PCh. 26.4 - Prob. 8PCh. 26.5 - Prob. 9PCh. 26.6 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.7 - Prob. 13PCh. 26.7 - Prob. 14PCh. 26.7 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Prob. 17PCh. 26.9 - Prob. 18PCh. 26.10 - Digestion of the tetrapeptide of Problem 26.18...Ch. 26.12 - Prob. 20PCh. 26.12 - Prob. 21PCh. 26.15 - Prob. 22PCh. 26.15 - Prob. 23PCh. 26.16 - Prob. 24PCh. 26.17 - Prob. 25PCh. 26.18 - Prob. 26PCh. 26 - Prob. 27PCh. 26 - Prob. 28PCh. 26 - Prob. 29PCh. 26 - Prob. 30PCh. 26 - Prob. 31PCh. 26 - Prob. 32PCh. 26 - Prob. 33PCh. 26 - Prob. 34PCh. 26 - Prob. 35PCh. 26 - Prob. 36PCh. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - Prob. 39PCh. 26 - Prob. 40PCh. 26 - If you synthesized the tripeptide Leu-Phe-Ser from...Ch. 26 - Prob. 42PCh. 26 - Prob. 43PCh. 26 - Prob. 44PCh. 26 - Prob. 45DSPCh. 26 - Prob. 46DSPCh. 26 - Prob. 47DSPCh. 26 - Prob. 48DSPCh. 26 - Prob. 49DSPCh. 26 - Prob. 50DSP
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