Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 21, Problem 21.25P
Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollen’s solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.
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10.
Stereochemistry. Assign R/S stereochemistry for the chiral center indicated on the
following compound. In order to recieve full credit, you MUST SHOW YOUR WORK!
H₂N
CI
OH
CI
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11. () Stereochemistry. Draw all possible stereoisomers of the following compound. Assign
R/S configurations for all stereoisomers and indicate the relationship between each as
enantiomer, diastereomer, or meso.
NH2
H
HNH,
-18
b)
8.
Indicate whether the following carbocation rearrangements are likely to occur
Please explain your rational using 10 words or less
not likely to occur
• The double bond is still in the
Same position
+
Likely
to oc
occur
WHY?
-3
H3C
Brave
Chair Conformers. Draw the chair conformer of the following substituted
cyclohexane. Peform a RING FLIP and indicate the most stable
conformation and briefly explain why using 20 words or less.
CI
2
-cobs ??
MUST INDICATE H -2
-2
Br
EQ
Cl
OR
AT
Br
H&
most stable
WHY?
- 4
CH
12
Conformational Analysis. Draw all 6 conformers (one above each letter) of the
compound below looking down the indicated bond. Write the letter of the
conformer with the HIGHEST and LOWEST in energies on the lines provided.
NOTE: Conformer A MUST be the specific conformer of the structure as drawn below
-4 NOT
HOH
OH
3
Conformer A:
Br
OH
A
Samo
Br H
04
Br
H
H3
CH₂
H
anti
stagere
Br CH
clipsed
H
Brott
H
IV
H
MISSING 2
-2
B
C
D
E
F
X
6
Conformer with HIGHEST ENERGY:
13. (1
structure
LOWEST ENERGY:
Nomenclature. a) Give the systematic (IUPAC) name structure. b) Draw the
corresponding to this name. HINT: Do not forget to indicate stereochemistry
when applicable.
a)
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Parent name (noname)
4 Bromo
Sub = 2-methylethyl-4 Bromo nonane
b) (3R,4S)-3-chloro-4-ethyl-2,7-dimethyloctane
# -2
-2
Chapter 21 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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