Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Textbook Question
Chapter 15.2, Problem 15.3P
Problem 15-3
Assign an R or S configuration to the single stereocenter in glyceralde- hyde, the simplest carbohydrate (Chapter 20).
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Question 23
Which of the following choices represents the Fischer projection of the compound shown?
Br
Br
HBr
H+Br
I
I
|||
||
OV
OIV
I
-Br
Br- -H
II
#F
Br
Br
III
Br
H+ Br
Br-H
-I
H
IV
H
H―Br
Br H
Br
V
PROBLEM 5-21
Which of the following compounds are chiral? Draw each compound in its most symmetric con-
formation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso
compounds. You may use Fischer projections if you prefer.
(a)
meso-2,3-dibromo-2,3-dichlorobutane
(b) (±)-2,3-dibromo-2,3-dichlorobutane
(c) (2R,3S)-2-bromo-3-chlorobutane
(d) (2R,3S)-2,3-dibromobutane
(e) (R, R)-2,3-dibromobutane
(f)
H-
HO
CHO
-OH
-H
CH₂OH
H
Br
H.
CH₂
H
CH₂
H
Br
(h) H
Br
CH₂
H
H
CH₂
H
Br
Problem Three
a) Tamoxifen is a breast cancer drug.
i) Identify which geometrical isomer it is by assigning a one-letter stereodescriptor:
ii) Predict the acid-base behaviour of Tamoxifen and name its functional groups
b) i) The Parkinson's disease drug Levodopa is shown. Which one-letter
stereodescriptor (S or R) describes its chiral centre?
your
HO.
HO
NH₂
OH
Chapter 15 Solutions
Introduction to General, Organic and Biochemistry
Ch. 15.1 - Prob. 15.1PCh. 15.2 - Problem 15-2 Assign priorities to the groups in...Ch. 15.2 - Problem 15-3 Assign an R or S configuration to the...Ch. 15.3 - Problem 15-4 3-Amino-2-butanol has two...Ch. 15.3 - Prob. 15.5PCh. 15.3 - Prob. 15.6PCh. 15 - 15-7 Answer true or false. The cis and trans...Ch. 15 - 15-8 What does the term “chiral” mean? Give an...Ch. 15 - 15-9 What does the term “achiral” mean? Give an...Ch. 15 - 15-10 Define the term “stereoisomer.” Name three...
Ch. 15 - 15-11 In what way are constitutional isomers...Ch. 15 - 15-12 Which of the following objects are chiral...Ch. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - 15-15 Explain why the carbon of a carbonyl group...Ch. 15 - 15-16 Which of the following compounds contain...Ch. 15 - 15-17 Which of the following compounds contain...Ch. 15 - Prob. 15.18PCh. 15 - 15-19 Draw the mirror image for each molecule: OH...Ch. 15 - Prob. 15.20PCh. 15 - 15-21 Answer true or false. For a molecule with...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - 15-26 For centuries, Chinese herbal medicine has...Ch. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - 15-30 (Chemical Connections 15A) What does it mean...Ch. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15-35 Following are structural formulas for three...Ch. 15 - Prob. 15.36PCh. 15 - 15-37 Consider a cyclohexane ring substituted with...Ch. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - 15-41 Compound A(C5Hh, is not optically active and...Ch. 15 - Prob. 15.42PCh. 15 - 15-43 Triamcinolone acetonide, the active...Ch. 15 - 15-44 Consider the structure of the...Ch. 15 - Prob. 15.45PCh. 15 - 15-46 Consider Lunesta, a nonbenzodiazepine...Ch. 15 - Prob. 15.47P
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