Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 3.4, Problem 3.6P
Interpretation Introduction
Interpretation:
A complete stereochemical name for the given compound has to be given.
Concept Introduction:
Priority rules:
- Priorities based on
atomic number
- When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center
- Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.
For example,
- Priority assignment is made at the first point of difference between groups (should not be based on the larger group).
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Q2: Ranking Acidity
a) Rank the labeled protons in the following molecule in order of increasing pKa. Briefly
explain the ranking. Use Table 2.2 as reference.
Ha
Нь
HC
H-N
Ha
OHe
b) Atenolol is a drug used to treat high blood pressure. Which of the indicated N-H bonds is
more acidic? Explain. (Hint: use resonance structures to help)
Name the functional groups on atenolol.
H
H-N
atenolol
Ν
H-N
OH Н
Answer d, e, and f
If the rotational constant of a molecule is B = 120 cm-1, it can be stated that the transition from 2←1:a) gives rise to a line at 120 cm-1b) is a forbidden transitionc) gives rise to a line at 240 cm-1d) gives rise to a line at 480 cm-1
Chapter 3 Solutions
Organic Chemistry
Ch. 3.2 - Prob. 3.1PCh. 3.3 - Assign priorities to the groups in each set. (a)...Ch. 3.3 - Prob. 3.3PCh. 3.4 - Following are stereorepresentations for the four...Ch. 3.4 - Prob. 3.5PCh. 3.4 - Prob. 3.6PCh. 3.5 - How many stereoisomers exist for...Ch. 3.5 - How many stereoisomers exist for...Ch. 3.7 - Prob. 3.9PCh. 3.7 - Prob. 3.10P
Ch. 3.8 - If the side chain of the amino add is a methyl...Ch. 3.8 - Prob. BQCh. 3.8 - The amino acids cysteine and serine are shown....Ch. 3.8 - Prob. DQCh. 3.8 - As stated, proteins are stereochemically pure...Ch. 3.8 - As stated, proteins are stereochemically pure...Ch. 3 - Prob. 3.11PCh. 3 - One reason we can be sure that sp3-hybridized...Ch. 3 - Which compounds contain chiral centers? (a)...Ch. 3 - Prob. 3.15PCh. 3 - Prob. 3.16PCh. 3 - Prob. 3.17PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.19PCh. 3 - Assign priorities to the groups in each set. (a) H...Ch. 3 - Following are structural formulas for the...Ch. 3 - Following is a staggered conformation for one of...Ch. 3 - Prob. 3.23PCh. 3 - When oxaloacetic acid and acetyl-coenzyme A...Ch. 3 - Prob. 3.25PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Prob. 3.30PCh. 3 - Which of the following are meso compounds?Ch. 3 - Prob. 3.32PCh. 3 - Prob. 3.33PCh. 3 - Which of the following compounds are chiral?...Ch. 3 - Prob. 3.35PCh. 3 - Prob. 3.36PCh. 3 - Prob. 3.37PCh. 3 - The chiral catalyst (R)-BINAP-Ru is used to...Ch. 3 - Prob. 3.39P
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