Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Question
Chapter 4, Problem 53P
Interpretation Introduction
Interpretation: Biosynthesis of corticosterone from progesterone takes place in two steps. The value of
Concept introduction: Hess's law states that when the reactants are converted to products the change of enthalpy (i.e. the heat of reaction at constant pressure) does not dependent on the pathway between the initial and final states.
Hess’s law states that enthalpy changes are additive. Thus, for a single reaction.
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4.
Protonation of alcohol A and subsequent loss of water, produces the intermediate B.
CH3
CH;
CH, CH, — с — сH, CH,
CH;CH, -
C- CH, CH;
|
OH
A
B
(a)
(i)
Name alcohol A.
(11)
What type of species is intermediate B?
(iii) Draw the structures of the two alkenes which can be formed from species B by
removal of a proton. Label as C the alkene which shows geometrical isomerism.
(b)
The intermediate B is readily attacked by nucleophiles such as water.
What is the essential feature of a nucleophile?
(c)
State what final colour you would see if alcohol A were warmed with acidified
potassium dichromate(VI). Explain your answer.
Colour
Explanation .
(ii) Draw two structural isomers of alcohol A which form branched chain ketones when
heated with acidified potassium dichromate(VI), but which could not form alkene C
on dehydration.
5. Consider the synthesis of 2-butanone from butyne:
Hg2+
CH3CH,-C=C–H
CH3CH, Ĉ
-CH3
H3o*
(i) Draw the structure of the compound D.
(ii) Compound D isomerizes to form 2-butanone. What is this isomeric process called?
(iii) Use the mechanism to show the conversion of compound D to 2-butanone.
Please give the main substitution product for each of the following reactions, and indicate the dominant mechanism:
(a) 1-bromopropane + NaOCH3 →
(b) 3-bromo-3-methylpentane + NaOC2H5 →
Chapter 4 Solutions
Organic Chemistry: Structure and Function
Ch. 4.1 - Prob. 4.1ECh. 4.1 - Prob. 4.3TIYCh. 4.2 - Prob. 4.4ECh. 4.2 - Prob. 4.6TIYCh. 4.3 - Prob. 4.7ECh. 4.4 - Prob. 4.8ECh. 4.4 - Prob. 4.10TIYCh. 4.4 - Prob. 4.11ECh. 4.4 - Prob. 4.12ECh. 4.4 - Prob. 4.14TIY
Ch. 4.6 - Prob. 4.15ECh. 4.7 - Prob. 4.16ECh. 4.7 - Prob. 4.17ECh. 4.7 - Prob. 4.18ECh. 4 - Prob. 21PCh. 4 - Prob. 22PCh. 4 - Prob. 23PCh. 4 - Prob. 24PCh. 4 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Prob. 27PCh. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - Prob. 40PCh. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - Prob. 43PCh. 4 - Prob. 44PCh. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Prob. 47PCh. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60P
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