Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 23, Problem 3LGP
Interpretation Introduction
Interpretation:
On the basis of given information, the structures of the required terpene and its isoprene unit are to be elucidated.
Concept introduction:
Terpenes are largely found as constituents of essential oils. They are mostly hydrocarbons.
The building block is a five-carbon isoprene unit
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An acidic liquid has a broad band at 3300 cm
a sharp band at 1710 cm in the infrared spectrum.
One mole of this unknown reacts with one mole of
NaOH. The ¹H NMR spectrum shows three peaks
in the ratio 2 : 2 : 1. Microanalysis gave C, 33.2 %;
H, 4.6%; C1, 32.7%.
Deduce the structure of the unknown.
Spell out the full name of the compound.
The oxidation of 3-pentanol to 3-pentanone was performed in the lab and an IR was taken of the finished product.
(a) what are the key functional groups in the starting material, 3-pentaol?
(b) what are the key functional groups in the product, 3-pentanone?
(c) based on the IR spectrum below, was the experiment successful, and, if so, how pure was the product? Explain your reasoning.
(d)
Ozonolysis of 3,4-dimethyl-3-hexene gives compound D.
(i)
Write the reaction step for the formation of D by including the
appropriate reagents.
(ii)
The mass spectrum of compound D shows a fragment ion peak at m/z
57. Propose the structure of this fragment ion.
(ii)
Identify the more stable resonance of the proposed structure in (ii).
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. 12PPCh. 23 - Prob. 13PPCh. 23 - Prob. 14PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 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. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Prob. 27PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGP
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