ORGANIC CHEM W/BIOLOGICAL TOP. ACCESS
6th Edition
ISBN: 9781264382545
Author: SMITH
Publisher: MCG CUSTOM
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Chapter 22.6, Problem 19P
Interpretation Introduction
Interpretation: The two different crossed Claisen reactions that form avobenzone are to be shown.
Concept Introduction: In crossed claisen condensation reaction, the base abstracts the acidic proton from
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Draw a Lewis structure for each of the following molecules and assign
charges where appropriate. The order in which the atoms are connected
is given in parentheses.
a. CIFCIF
b. BrCNBrCN
0
c. SOCI2 × (CISCIO) SOC₁₂ (CISCI)
You can draw both an octet and a valence
shell expanded structure. Considering the following structural information, which
is the better one: The measured S-OS-O bond length in SOC12SOCl2 is 1.43 Å.
For comparison, that in SO2SO2 is 1.43 Å [Exercise 1-9, part (b)], that in
CHзSOHCH3 SOH
d. CH3NH2CH3NH2
(methanesulfenic acid) is 1.66 A.
e. CH3OCH3 CH3 OCH3
NH2
f. N2H2× (HNNH) N2 H2 (HNNH)
g. CH2COCH₂ CO
h. HN3× (HNNN) HN3 (HNNN)
i. N20 × (NNO) N2O (NNO)
bre
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
Chapter 22 Solutions
ORGANIC CHEM W/BIOLOGICAL TOP. ACCESS
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 22.1 - Prob. 4PCh. 22.1 - Prob. 5PCh. 22.2 - Prob. 6PCh. 22.2 - Problem 24.7
Draw the products formed in each...Ch. 22.4 - Prob. 15PCh. 22.4 - Prob. 16PCh. 22.5 - Problem 24.16
What ester is formed when each...
Ch. 22.6 - Prob. 18PCh. 22.6 - Prob. 19PCh. 22.6 -
Draw the products of each reaction.
a. b.
Ch. 22.6 - Problem 24.20
Two steps in a synthesis of the...Ch. 22.7 - Prob. 22PCh. 22.8 - Problem 24.22
Which of the following compounds can...Ch. 22.8 - Prob. 24PCh. 22.8 - Problem 24.24
What starting materials are needed...Ch. 22 - Prob. 29PCh. 22 - 24.29 What steps are needed to convert A to B?
Ch. 22 - Prob. 31PCh. 22 - 24.31 Draw the product formed in each directed...Ch. 22 - Prob. 33PCh. 22 - 24.33 What starting materials are needed to...Ch. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - 24.36 Identify the structures of C and D in the...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - 24.39 Draw the product formed from a Claisen...Ch. 22 - Prob. 41PCh. 22 - 24.41 Even though B contains three ester groups, a...Ch. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - 24.44 Vetivone is isolated from vetiver, a...Ch. 22 - Draw the product of each Robinson annulation from...Ch. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - 24.52 Draw a stepwise mechanism for the following...Ch. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56PCh. 22 - Prob. 57PCh. 22 - Prob. 58PCh. 22 - Prob. 59PCh. 22 - 24.62 Devise a synthesis of each compound from ,...Ch. 22 - Prob. 63P
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