ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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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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(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).
Name the following compounds A and B.
How could you distinguish these two molecules by using 1H NMR and IR techniques?
Propose an analytical technique to determine the iron content of these compounds.
Calculate the mass percentages of C and H of compound B (C: 12.01 g/mol; H: 1.008 g/mol; Fe: 55.845 g/mol).
A compound of mass 149 has the following elemental analysis : C = 80.48%, H=10.13%,
N=9,39%. The IR, 1H and 13C NMR spectra are given below. In the 13C spectrum decoupled from the 1H the nature
of the carbon was determined using the 13C DEPT spectra (not shown here). Assign the spectra and identify
the compound. You can: 1) Calculate the molecular formula of compound A; 2) Calculate the unsaturation number; 3)
Analysethe characteristic bands of the IR spectrum; 4) Assign and interpret all the data from the 1H and 13C NMR
spectra).
3500
1800 1600 1400 1200 1000 800 600 cm¹
го протру
AU
I=3
I=1
I=1
4.0
8.0
I=2
I=2
71
150
3000
с
7.0
CH
C
125
2500
6.0
CH
2000
2,8; 40 ppm
5.0
100
Explain why the answer Is this one :
4,5 (6,8; 115)
C
CH3-NH THÀ
ppm
ppm 75
3.0
7,2; 128)
132
50
CH₂
2.0
CH
CH₂
25
CH 3
-CH
3,2; 27 CH3
I=6
1.0
1,2; 22
Chapter 23 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
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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