Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 13.17, Problem 25P
Interpretation Introduction
Interpretation:
The name of the isomers that are separately formed under kinetically and thermodynamically control reactions of sulfonation of naphthalene is to be determined. The reason for the stability of one isomer over other is to be explained.
Concept Introduction:
On the basis of
On the basis of
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When we have discussed the enol-keto tautomerization of ketones in class, the isomerization has been
facililated by an acid or base catalyst, with most ketones heavily favoring the carbonyl isomer at equilibrium.
However, samples of the ketone below in its pure form (with no acid, base or water present) contain nearly
10% of the enol form!
OH
-90%
-10%
From this data, we can infer that the enol isomer of this ketone is particularly stable. Explain the stability of
this enol, using terms and ideas that we have discussed in this unit.
Draw the structure(s) of the major organic product(s) of the following reaction.
You need not specify stereochemistry.
If more than one product is formed, draw all structures in the same sketchpad.
1. LIAIH4/dry Et₂O
2. aqueous HCI
1. Which compound is expected to have a higher melting point, 1-pentanol or 1-pentanal? Explain
2. Which compound is expected to be more soluble in water, propanal or butanal? Explain.
3. Why is acetyl chloride more reactive towards hydrolysis than ethyl acetate?
Chapter 13 Solutions
Organic Chemistry - Standalone book
Ch. 13.2 - Based on Hammonds postulate which holds that the...Ch. 13.3 - Prob. 2PCh. 13.3 - Using : O =N+= O : as the electrophile, write a...Ch. 13.4 - Prob. 4PCh. 13.5 - Prob. 5PCh. 13.6 - Prob. 6PCh. 13.6 - Write a reasonable mechanism for the formation of...Ch. 13.6 - tert-Butylbenzene can be prepared by alkylation of...Ch. 13.6 - Prob. 9PCh. 13.7 - The reaction shown gives a single product in 88...
Ch. 13.7 - Prob. 11PCh. 13.8 - Using benzene and any necessary organic or...Ch. 13.10 - Prob. 13PCh. 13.11 - Prob. 14PCh. 13.12 - Prob. 15PCh. 13.12 - Prob. 16PCh. 13.13 - Prob. 17PCh. 13.13 - Prob. 18PCh. 13.14 - Reaction of chlorobenzene with p-chlorobenzyl...Ch. 13.15 - Prob. 20PCh. 13.15 - Prob. 21PCh. 13.15 - Prob. 22PCh. 13.16 - Prob. 23PCh. 13.16 - Prob. 24PCh. 13.17 - Prob. 25PCh. 13.18 - Prob. 26PCh. 13.19 - Write the structure of the expected product from...Ch. 13.20 - Prob. 28PCh. 13.20 - Prob. 29PCh. 13.21 - Prob. 30PCh. 13.21 - Offer an explanation for the observation that...Ch. 13.21 - Prob. 32PCh. 13 - Write the structure of the organic product in each...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Treatment of the alcohol shown with sulphuric acid...Ch. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Arrange the following five compounds in order of...Ch. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Give reagents suitable for carrying out each of...Ch. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Which is the best synthesis of the compound shown?Ch. 13 - What combination of acyl chloride or acid...Ch. 13 - A standard synthetic sequence for building a...Ch. 13 - Prob. 54PCh. 13 - Prob. 55PCh. 13 - Prob. 56PCh. 13 - Prob. 57PCh. 13 - Prob. 58PCh. 13 - Prob. 59PCh. 13 - Prob. 60DSPCh. 13 - Prob. 61DSPCh. 13 - Prob. 62DSPCh. 13 - Prob. 63DSP
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