Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Textbook Question
Chapter 13, Problem 13.26P
Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two methyls on the isopropyl group in ascaridole appear in its 1H-NMR spectrum as four lines of equal intensity, with two sets of two each separated by 7 Hz.
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Write structural formulas for the major products by
doing addition reactions
1. You must add H2 as Pt is catalyst it does not take part in reactions
only speed up the process
H₂
CH2=CH-CH3
Pt
2. Add HCI break it into H and Cl
CH3
HCI
3. Add Br2 only CC14 is catalyst
CH3-CH=CH2
B12
CCl4
4. Add water to this and draw major product, H2SO4 is catalyst you have add
water H20 in both the reaction below
H₂SO4
CH3-CH=CH2
CH3
H2SO4/H₂O
CH3-C=CH2
reflux
?
Plan the synthesis of the following compound using the starting
material provided and any other reagents needed as long as
carbon based reagents have 3 carbons or less. Either the
retrosynthesis or the forward synthesis (mechanisms are not
required but will be graded if provided) will be accepted if all
necessary reagents and intermediates are shown (solvents and
temperature requirements are not needed unless specifically
involved in the reaction, i.e. DMSO in the Swern oxidation or
heat in the KMnO4 oxidation).
H
H
Hint These are benzene substitution reactions.
ALCI3 and UV light are catalyst no part in reactions and triangle A means
heating.
A. Add ethyl for Et in benzene ring alkylation reaction EtCl =
CH3CH2CL
1) EtC1 / AlCl3 / A
?
B: Add Br to benzene ring ( substitution)
2) Br₂ / uv light
?
C Add (CH3)2 CHCH2 in benzene ring ( substitution)
(CH3)2CHCH,C1 / AICI,
?
Chapter 13 Solutions
Organic Chemistry
Ch. 13.2 - Calculate the ratio of nuclei in the higher spin...Ch. 13.5 - State the number of sets of equivalent hydrogens...Ch. 13.5 - Each compound gives only one signal in its 1H-NMR...Ch. 13.6 - The line of integration of the two signals in the...Ch. 13.7 - Following are two constitutional isomers with the...Ch. 13.8 - Following are pairs of constitutional isomers....Ch. 13.10 - Following is a 1H-NMR spectrum of 2-butanol....Ch. 13.11 - Explain how to distinguish between the members of...Ch. 13 - Prob. 13.9PCh. 13 - Prob. 13.10P
Ch. 13 - Prob. 13.11PCh. 13 - Following are structural formulas for three...Ch. 13 - Following arc structural formulas for the cis...Ch. 13 - Prob. 13.14PCh. 13 - Following are three compounds with the molecular...Ch. 13 - Following are 1H-NMR spectra for compounds D, E,...Ch. 13 - Following are 1H-NMR spectra for compounds G, H,...Ch. 13 - Propose a structural formula for compound J,...Ch. 13 - Compound K, molecular formula C6H14O, readily...Ch. 13 - Compound M, molecular formula C5H10O, readily...Ch. 13 - Following is the 1H-NMR spectrum of compound O,...Ch. 13 - Treatment of compound P with BH3 followed by...Ch. 13 - The 1H-NMR spectrum of compound R, C6H14O,...Ch. 13 - Write structural formulas for the following...Ch. 13 - Prob. 13.25PCh. 13 - Ascaridole is a natural product that has been used...Ch. 13 - The 13C-NMR spectrum of 3-methyl-2-butanol shows...Ch. 13 - Prob. 13.28P
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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY