Solutions Manual for The Art of Writing Reasonable Organic Reaction Mechanisms – Step-by-Step Mechanism Solutions

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SOLUTIONS MANUAL

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Solutions manual for the art of writing reasonable organic reaction
mechanisms
Answers To Chapter 1 In-Chapter Problems.

1.1. The resonance structure on the right is better because every atom has its
octet. 1.2.
O– O




CH2 + CH2 CH2 CH2



C O C O




NMe2 NMe2 NMe2



NMe2 NMe2 NMe2




N N N N N

H3C H3
N N CH2
H3C CH C
2

H

3C

, 1

the second structure is hopelessly strained
O O

, Chapter 1 2



1.3.
2 sp3
sp
O sp O– sp3 CH3 CH3
2 3
2
sp2 N sp3 sp sp
Ph N
sp H3C H3C CH3
O Ph
s sp2 sp3 sp3
p sp2 all sp2 all sp2 CH
3
sp3

F sp2 H
3
2 O sp
sp H CH
sp
2
sp2 sp 2
Bsp 2
HC 3
F F H H

1.4. The O atom in furan has sp2 hybridization. One lone pair resides in the p orbital and is used
in resonance; the other resides in an sp2 orbital and is not used in resonance.

1.5.
(a) No by-products. C(1–3) and C(6–9) are the keys to numbering.
3 10
1 2 O
5 12 12
4 OH 9 O
11 H+, H2O 1
6 13 2 4 5
8
9
Ph Ph
7 8 6
7 11 13
O10 3
H

(b) After numbering the major product, C6 and Br25 are left over, so make a bond between
them and call it the by-product.
13 14 24
12 15
H Br 16
21 15
20 O 14 17
10
HN 11 16 24
2
13 12 21O 6 25
5
11 18
1 Br 9 19 Br Br 1
Br N 20 Me Br
8 17
2 18 10
19
9
2
8
3 7 OMe 3 4
22 23 7 OMe
4
5 OMe6 O5

1.6. (a) Make C4–O12, C6–C11, C9–O12. Break C4–C6, C9–C11, C11–O12.
(b) Make C8–N10, C9–C13, C12–Br24. Break O5–C6, C8–C9.