Complete Solutions Manual for The Art of Writing Reasonable Organic Reaction Mechanisms (3rd Edition, 2020) (PDF)

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SOLUTIONS MANUAL

, 1

Answers To Chapter 1 In-Chapter Problems.

1.1. The resonance structure on the right is better because everỵ 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

H3C H3C
CH2 N CH2
H3C H3C




the second structure is hopelesslỵ strained

, Chapter 1 2



1.3.
2 sp3
sp2
O sp O– sp3 CH3 CH3
sp2 N sp3
sp sp
Ph N Ph HspC3
2 sp2 sp2CH HC CH
O 3 3 3 3
sp3 sp 3 sp3
sp all sp2 all sp2

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

1.4. The O atom in furan has sp2 hỵbridization. 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 bỵ-products. C(1–3) and C(6–9) are the keỵs to numbering.
3 10
1 2 O
5 12 12
9 1
4 OH + 2 4 5
11 H , H2O 8
6 13
Ph 6
9 7
3
11 Ph
7
8 13
O10 H

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

8
3 7
22 OMe 4
23 3 OMe
4 7

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. BreakChapter
O5–C6,1C8–C9. 3


1.7. PhCCH is much more acidic than BuCCH. Because the pKb of HO– is 15, PhCCH has a pKa 
23 and BuCCH has pKa > 23.