ORGANIC CHEMISTRY W/ALEKS
6th Edition
ISBN: 9781264905430
Author: SMITH
Publisher: MCG CUSTOM
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Chapter 21, Problem 65P
Interpretation Introduction
Interpretation: The synthesis of anastrozole from the given compounds is to be devised.
Concept introduction: Alkylation of
The first step is abstraction of proton and second step is attack of electrophile to form alkylated product.
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The reaction sequence shown in Scheme 5 demonstrates the synthesis of a
substituted benzene derivative Q.
wolsd works 2
NH2
NaNO2, HCI
(apexe) 13× (1
HNO3, H2SO4
C6H5CIN2
0°C
HOTE
CHINO₂
N
O
*O₂H (
PO
Q
Я
Scheme 5
2 bag abouoqmics to sounde odi WEIC
(i)
Draw the structure of intermediate O.
[2 marks]
to noitsmot od: tot meinedogm, noit so oft listsb ni zaupaib bas wa
(ii) Draw the mechanism for the transformation of aniline N to intermediate O.
Spoilage
(b)
[6 marks]
(iii) Identify the reagent X used to convert compound O to the iodinated compound
[tom E
P.
vueimado oilovonsa ni moitos nolisbnolov ayd toes ai tedw nisiqx
(iv) Identify the possible structures of compound Q.
[2 marks]
[2 marks]
[shom 2]
(v)
bus noires goiribbeolovo xnivollot adj to subora sidab
Draw the mechanism for the transformation of intermediate P to compound Q.
[5 marks]
vi
(vi) Account for the regiochemical outcome observed in the reaction forming
compound Q.
[3 marks]
PROBLEM 4 Solved
Show how 1-butanol can be converted into the following compounds:
a.
PROBLEM 5+
b.
d.
-C=
N
Which alkene is the major product of this dehydration?
OH
H2SO4
heat
Chapter 21 Solutions
ORGANIC CHEMISTRY W/ALEKS
Ch. 21.2 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 21.2 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 21.3 - Prob. 5PCh. 21.3 - Problem 23.5 Which bonds in the following...Ch. 21.3 - Prob. 7PCh. 21.3 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.4 - Prob. 10PCh. 21.5 - Prob. 11PCh. 21.7 - Problem 23.11 Draw the products of each...
Ch. 21.7 - Problem 23.12 Draw the products of each reaction....Ch. 21.7 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.8 - Prob. 17PCh. 21.8 - Prob. 18PCh. 21.8 - Problem 23.18 How can pentan-2-one be converted...Ch. 21.8 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 21.9 - Problem 23.20 Which of the following compounds...Ch. 21.9 - Problem 23.21 Draw the products of each...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.9 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.10 - Prob. 27PCh. 21.10 - Prob. 28PCh. 21.10 - Prob. 29PCh. 21 - 23.29 Draw enol tautomer(s) for each compound....Ch. 21 - 22.30 The cis ketone A is isomerized to a trans...Ch. 21 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - 23.35 Rank the labeled protons in each compound in...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - 23.38 Acyclovir is an effective antiviral agent...Ch. 21 - 23.39 Explain why forms two different alkylation...Ch. 21 - Prob. 40PCh. 21 - 23.42 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - 23.45 Devise a synthesis of valproic acid , a...Ch. 21 - Prob. 57PCh. 21 - 23.57 Draw a stepwise mechanism showing how two...Ch. 21 - 23.58 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 65PCh. 21 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...
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