Errors in Klien study guide 1st edition - Berkeley City College

Errata Sheet for Klein, Organic Chemistry 1e Solutions Manual (Updated 6/18/12) Chapter 1 . p 10 - problem 1.38b, the nitrogen atom should have a lone pair (to
complete its octet). Chapter 2 . p 22 - 2.21g should be: "Violates second rule by giving five bonds to
a carbon atom, and violates first rule by breaking a single bond." . p 22 - 2.21h should be: "Violates second rule by giving five bonds to
a carbon atom, and violates first rule by breaking a single bond." . p 35 - Problem 2.55j - the final resonance structure was missing a pi
bond, and should be drawn as follows: [pic] Chapter 3 . p 45 - problem 3.14 - last sentence was changed to read "Therefore,
the proton on the sulfur atom will definitely be more acidic than the
proton on the nitrogen atom." Chapter 4 . p 60- problem 4.1H- changed 'cycloheptene' to 'cycloheptane'. . p 62 - problem 4.8 - The compound has only three substituents (not
four), as shown below: [pic] . p 63 - problem 4.10L - 2,2,5-trimethylpentane was changed to 2,2,4-
trimethylpentane . p 64 - problem 4.20A - in the highest energy conformation, a methyl
group was missing. The Newman projection was corrected by replacing
an H (connected to the back carbon) with a methyl group. . p 67 - 4.33c and 4.33d - the methyl group should be in an equatorial
position, and the chloro groups should be in axial positions. . p 75 - Problem 4.67a) the trans isomer is expected . p 76 - Problem 4.69a, the chair conformations should be drawn as
follows:: [pic] Chapter 5 . p 83 - problem 5.16 - The problem asks for the enantiomer, so the
observed rotation should be negative, rather than positive. . p 84 - The answer is "5.23e has three planes of symmetry" . p 90 - problem 5.50c) 5% of the mixture is (S)-carvone . p 90 - problem 5.51. The last four solutions were renumbered (m,n,o,p
rather than l,m,n,o) Chapter 6 . p 95 - Problem 6.1a - Br-Br should be +193kJ/mol and the sum for ?H?
should be -63kJ/mol . p 96 - problem 6.4a - the last full sentence on this page was changed
to read "A high temperature will cause the second term to dominate,
giving rise to a negative value of ?G. . p 97 - problem 6.4a - second line on the page was changed to read
"dominate, giving rise to a positive value of ?G. . p 97 - problem 6.4d - the last line of the problem was changed to read
"dominate, giving rise to a negative value of ?G. Chapter 7 . p 118 - problem 7.5. The resonance structures of the intermediate were
each missing a methyl group. The correct resonance structures are: [pic] . p 120 - deleted 7.16d, since that exercise does not appear in the
text. . p 122 - 7.21e and 7.21f - the proton source in the mechanism should be
MeOH2+ rather than H3O+ . p 124 - 7.24d - the starting material should be benzyl chloride,
rather than benzyl bromide . p 125 - problem 7.28. Structures in part a and part b should not
contain fluoro groups. The fluoro groups were deleted. . p 126 - Problem 7.33c. The answer should be: 1) TsCl, py, 2) NaI. . p 126 - Problem 7.33i was deleted, because there is no corresponding
problem in the text. . p 127 - problem 7.36. There were two answers for part d. The second
answer was incorrect and was deleted. Also, 7.36f does not appear in
the textbook, so the solution for 7.36f was deleted from the solutions
manual.
Chapter 8 . p 147 - problem 8.18b - answer should be: [pic] . p 147 - problem 8.18c - answer should be: [pic] . p 155 - problem 8.45 - first sentence was changed to read "The
substrate is sterically hindered (severely) so SN2 cannot occur at a
reasonable rate. . p 163 - Problem 8.70 - The identity of the halogen in the transition
state should be Cl, rather than Br. . p 164 - Problems 8.75a and 8.75c - sodium ethoxide should be used
(sodium hydroxide was not listed as an option in the problem
statement) . p 166 - 8.78c - the starting material has only one chirality center,
and therefore, the methyl group should not be on a wedge. It should
be on a straight line. . p 167 - problems G and H should be changed to J and L respectively. . p 167 - problems J and K - changed as follows: [pic] Chapter 9 . p 177 - problem 9.7b - the product was missing a methyl group (it
should be 3-bromo-3-methylpentane). . p 199 - problem 9.74 - changed 1) from NaOMe to tBuOK. Chapter 10 . p 216 - problem 10.33A - changed 1) from NaOMe to tBuOK. Chapter 12 . p 256 - problem 12.3B - changed 1) from NaOMe to tBuOK. Chapter 13 . p 289 - Problem 13.22d was mislabeled as 13.22c. . p 291- the top four solutions were renumbered (c,d,e,f rather than
d,e,f,g) Chapter 14 . p 319 - Problem 14.12a - the second name given should be: 2,2-
dimethyloxirane . p 319 - Problem 14.12b - the second name given should be: 2,2-
diphenyloxirane . p 319 - Problem 14.13a - the second name given should be: (S)-2-methyl-
2-phenyloxirane . p 319 - Problem 14.13b - the second name given should be: (1R,2R)-2-
ethyl-3-propyloxirane . p 319 - Problem 14.13c - the second name given should be: (1S,2R)-2-
isopropyl-3-methyloxirane
Chapter 15 . p 347 - problem 15.10E - change to ketone . p 347 - problem 15.10F - change to ROH . p 351 - The third sentence in the answer should be: "The second
spectrum has a peak at M-15, signifying the loss of a methyl group. " . p 353-354 - Problem 15.40a-d should also mention the Csp3-H stretching
signals that are expected just below 3000 cm-1. . p 354 - Problem 15.42a-f should also mention the Csp3-H stretching
signals that are expected just below 3000 cm-1. Chapter 16 . p 365 - problem 16.7A - see change below (boxed in red) [pic] . p 365 - problem 16.7B - see change below (boxed in red) [pic] . p 366 - The structure for problem 16.7d was changed in the textbook
(to avoid having the issue of diastereotopic protons). The answer for
the corrected structure is: [pic] . p 370- problem 16.16 - sentences were added: "The following is just
one possibility. There are many correct answers." . p 372 - problem 16.21 - the last four solutions were renumbered
(c,d,e,f rather than d,e,f,g) . p 372 - Problem 16.21e - the structures were changed to avoid having
diastereotopic protons. The correct answer should be : "The first
compound will have only two signals in its 1H NMR spectrum, while the
second compound will have four signals." Chapter 17 . p 393 - problem 17.17 - change s trans to s-cis in both instances . p 393 - problem 17.18 - change s-cis to s trans in both instances . p 397 - Problem 17.28 - the second structure and the third structure
were missing a methyl group. . p 408 - Problem 17.65 - the penultimate structure, as well as the
previous structure, was missing a methylene group next to the carbonyl
group. The missing methylene group was inserted into each of these
structures. Chapter 18 . p 413 - The last answer should be labeled 18.e rather than 18.1f . p 413 - Problem 18.2b - the answer should be 5-bromo-2-hydroxytoluene . p 414 - problem 18.5b - the answer should be: 3-methylperoxybenzoic
acid or meta-methylperoxybenzoic acid . p 426 - problem 18.61A - last sentence was changed to read "The ring
with oxygen is not aromatic and not planar. Chapter 19 . p 436 - Problem 19.1 - In the last step of the mechanism, the base
that removes the proton should be an acetate ion. . p 445 - Problem 19.37a - the answer should read: "Each additional
nitro group serves as a reservoir of electron density and provides for
an additional resonance structure in the Meisenheimer complex, thereby
stabilizing the Meisenheimer complex and lowering the energy of
activation for the reaction." . p 445 - Problem 19.37b - the answer should read: "No, a fourth nitro
group would not be ortho or para to the leaving group, and would not
provide resonance stabilization for the Meisenheimer complex.
Therefore, we do not expect the temperature requirement to be
significantly lowered" . p 447 - problem 19.43 - this problem was changed in the textbook -
ethylbenzene was replaced with toluene. As a result, the solution was
changed as well. The reagents should be CH3Cl and AlCl3, rather than
EtCl and AlCl3. This change was necessary in order to enable the next
step (formation of tribromomethylbenzene) to be performed. . p 462 - problem 19.72A - 5) was changed from Br2, AlBr3 to xs Br2,
AlBr3 Chapter 20 . p 475 - problem 20.11 - the answers for parts b and c were out of
order. . p 489 - problem 20.41A - change 1) from BH3 THF to Br2, hv . p 489 - problem 20.41E - the last reagent should be isopropyl amine. . p 490 - problem 20.41h was deleted, since there is no corresponding
exercise in the textbook. . p 492 - problem G - see change below (circled in green) [pic] . p 494 - The answer to problem 20.49 was changed to be: "The carbonyl
group of a ketone is unlikely to appear at C-1 because if it did, the
compound would likely be called an aldehyde rather than a ketone.
There are exceptions, such as 1-phenylketones (one example is 1-phenyl-
1-butanone). " . p 497 - problem 20.58 - see change below (