Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 23, Problem 18P
Propose structures for
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Alpha-phellandrene, C₁0H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular
formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula
C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds:
CHIC-CH HOCHSCHICH
CH(CH3)2
Propose a structure for alpha-phellandrene.
Alpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves
of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On
hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained.
Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the
following two compounds:
0
||
CH3C-CH
0
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●
Propose a structure for alpha-phellandrene.
(+
||
HCCH₂CHCH
I
CH(CH3)2
• You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
• In cases where there is more than one answer, just draw one.
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The ¹H NMR spectrum of a compound with the molecular formula C7H₁5Cl exhibits signals with relative integration 9:3:2:1. Propose a
structure for this compound.
4-chloroheptane
3-chloro-2,2-dimethylpentane
3-chloro-2,4-dimethylpentane
O2-chloro-2,3,3-trimethylbutane
Chapter 23 Solutions
Organic Chemistry
Ch. 23 - Prob. 1PPCh. 23 - Prob. 2PPCh. 23 - Prob. 3PPCh. 23 - Prob. 4PPCh. 23 - Prob. 5PPCh. 23 - Prob. 6PPCh. 23 - Prob. 7PPCh. 23 - Prob. 8PPCh. 23 - Prob. 9PPCh. 23 - Prob. 10PP
Ch. 23 - Prob. 11PPCh. 23 - Prob. 12PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 14PCh. 23 - Prob. 15PCh. 23 - When limonene (Section 23.3) is heated strongly,...Ch. 23 - Gadoleic acid (C20H38O2), a fatty acid that can be...Ch. 23 - 23.20 -Phellandrene and -phellandrene are isomeric...Ch. 23 - Prob. 19PCh. 23 - Prob. 20PCh. 23 - Prob. 21PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 23PCh. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGPCh. 23 - 23.1 Write an appropriate formula in each box.
Ch. 23 - Give a reagent that would distinguish between each...Ch. 23 - 23.3 What product would be obtained by catalytic...Ch. 23 - Prob. 4QCh. 23 - 23.5 The following compound is a:
(a)...Ch. 23 - Mark off the isoprene units in the previous...Ch. 23 - Prob. 7Q
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