Corrections to Bruice 7th Edition

p. 297, problem 98c. Either change the structure to:

H
H

or change the answer to:

p. 440, problem 50a. The product should butylmethyl ether (not pentane).

p. 544, The In in‐text Solution to 12a, the catecholborane derivative is missing a methyl group off of the
2‐ position of the vinyl group.

p. 647, problem 73a. The scale is off in the IR spectrum. The answer is 2‐hexanone and there are no
unsaturated C‐H stretches in this molecule. The C=O stretch should be at 1721 cm‐1.

p. 716, problem 76. The scale is off for the IR spectrum; it should be shifted by about 15‐20 cm‐1 lower.
There are no unsaturation in this molecule (the line of unsaturation has been crossed). The answer
book is also incorrect; ketones would have an IR frequency around 1715 or 1710 cm‐1 not 1730 cm‐1.

p. 790, Vanillin is drawn as a methyl ketone—make it an aldehyde.

p. 960‐962. Under “Summary of Reactions”

1. Electrophilic aromatic substitution reactions

a. The mechanisms are shown on pages 914 and 915. (not 927 and 928)

b. The mechanisms are shown on pages 916 and 917. (not 929, 930 and 931)

5 Reactions of aniline with nitrous acid (Section 19.23). The mechanisms are shown on page 953.
(not 966)

7. Formation of an azo compound (Section 19.22) The mechanism is shown on page 951. (not
964)
 8. Nucleophilic aromatic substitution reactions (Section 19.24). The mechanism is shown on
page 956. (not 969)

p. 1098, problem 73. Mutant should be variant. Mutations involve DNA.

p. 1159. The structure of folate is missing a C=O (in blue):

p. 1210. The title should be “nucleotides of adenosine” and “nucleotides of 2’‐deoxyadenosine” not
nucleosides. The nucleoside of the 2nd sentence should be nucleotide as they contain phosphate groups.

p. 1291. Problem 29a. The product should have terminal methyl group (not a methylene).

Corrections to the Solutions Manual, 7th Edition

p. 71, chapter 1, problem 73b. The correct possible structures are:

H H
C N N C N N
H H

p. 173, chapter 5, problem 34c. The question asks about the forward direction so the correct answer is
“The second step (k2), B to form C [not A].

p. 189, chapter 6, p. 189. 23d should be major:

OCH3

major
Br
p. 204, chapter 6, problem 78a: the answer should be:

CH3 CH3 These form in unequal amounts

Br Br as they are diastereomers.
The alkyl group can both be
Br Br equatorial if the cis dialkyl product forms
CH2CH3 CH2CH3 (the 1S 2S 3S product).

P. 212, problem 98c. If the textbook is correct, then the answer should be:

p. 224, chapter 7 problem 20d and 20e. The answers should be:

H
d.
O O
e. +
O

p. 311 problem 12E. If a carbocation forms, then the following resonance structures are possible:

Two elimina on products are possible and we would have one with a lower energy TS‡.

p. 449, problem 54a answer 1 should be 7 (not 5).

p. 466 problem 19. The acid that is produced by the reaction is HCl, with a pKa of ~ ‐6. Since the
protonated alcohol has a pKa of ~ ‐2, the alcohol is more likely to be protonated when in solution with
HCl than Cl‐, meaning excess alcohol should be used in the reaction, as well.

p. 527 problem 84. The reaction of the Wittig reagent (the 3rd molecule) is with acetone. Acetone has a
spurious mechanistic arrow in this step.

p. 531 problem 91. After attach by diazomethane on cyclohexanone, the mechanistic arrow should be
drawn from the ring and not from the bond that was just formed.
p. 591 problem 35.a. is not solved in the text, and 35.b refers to this answer. The correct starting
material (based on the 6th edition) is m‐dibromobenzene. The synthesis of this and the m‐nitrobenzoic
acid are shown below:

NO2 NO2 NH2 Br

HNO3 Br2 H2 NaNO2 CuBr
H2SO4 FeBr3 Pd/C HCl

Br Br Br

CH3 CO2H CO2H

CH3Cl Na2Cr2O7/HCl HNO3
AlCl3 or KMnO4/H+ H2SO4

NO2

p. 601 problem 56.a. –There should be a + formal charge on chlorine after attack of the AlCl3.

p. 603 problem 57.i.—After the second step of the synthesis, the catalyzed hydrogenation of the nitro
group, the product is still depicted as a nitro group and the reduced amine.

P. 810 problem 8 (2nd problem). The answer is given on p.1277 in the text (if this is a thermal reaction).
It should be trans with a disrotation. This was not fixed from the 6th edition.