Book Errors
You may have noticed a stunning similarity between the name of one of the authors who wrote the text book and the Study Guide we are using and my name. In fact, my wife and I wrote the study guide and I am a coauthor on the text. Unfortunately, there are some mistakes in these. We will post the mistakes here as the class comes across them. As incentive, if you are the first to mention in person or E-mail me the location of a mistake in the test or Study Guide, I will give you 1-3 dollars, depending on how grievous the error is. Several students made some good spending money last time through the course! (I am not kidding).
Errors found so far:
Textbook:
Page 23 Under "F. Carboxylic Amides" replace "is a derivative of a carboxylic acid in which the hydrogen of the carboxyl..." with "is a derivative of a carboxylic acid in which the hydroxyl of the carboxyl..."
Page 88 In the "How to" box, at the bottom, the (a) and (e) designations on the figure on the right (on carbons 1 and 2, should be reversed. The (a) should be attached to the methyl on carbon 1, and the (e) should be attached to the methyl on carbon 2.
Page 96 In example 2.15, the molecule on the lower right is "Octane", not "Decane".
Page 103 Problem 2.16a. The 4th C has attached CH2(CH3)2. This is not possible. It should read CH(CH3)2.
Page 186 In the second paragraph, third to the last line, replace "5.8 Kj (1.4 Kcal)/mol" with "4.2 Kj (1.0 Kcal)/mol".
Page 196 in the "Connections to Biological Chemistry" box there is an extra nonane structure just above the Linolenic acid structure. This should not be there.
Page 219 In the mechanism box, the structure in the lower right corner has a "+" sign that should not be there.
Page 223 In the mechanism box in the second mechanism, there is an arrow missing that should indicate a C-Br bond breaking.
Page 248 On the bottom arrow the reagent should read (R)-BINAP-Ru, not (S)-BINAP-Ru.
Page 271 In sthe solution to example 7.3, under the arrow it should read "H2O", not "NH2O"
Page 275 In the middle of the page, the name 2-Methyl-2-butane" should be "2-Methyl-2-butene".
Page 279 The enol structure in the middle of the page should be E, not A as shown because of syn addition stereoselectivity.
Page 284 For the reaction summary section, reaction 1, the product has an extra methyl group not present in the starting material alkyne.
Pg. 330 On the margin, the definition of electrophile, it should say "electron loving" not "nucleus loving".
Pg. 340 In the middle of the page, in bullet 1. "left to right" should actually read "right to left".
Pg. 357 In the mechanism box at the top of the page, the Br atom on the right should have another lone pair and a negative charge.
Page 389 On the first line under the Figure 10.3 figure caption, replace "ether (bp 24°C)." with "ether (bp -24°C)".
Page 396 In the upper mechanism box, for Step 3. Replace "of the 3° carbocation (an electrophile) with chloride ion..." with "of the 3° carbocation (an electrophile) with bromide ion..." For the structures below, replace the Cl anion with Br (left side) and replace the Cl on the product side with Br as well. The product's name should be "2-Bromo-2-methylpropane (tert-Butyl bromide)" not "2-Chloro-2-methylpropane (tert-Butyl chloride)".
Study Guide:
Page 7, Problem 1.28(f) A lone pair of electrons should be added to the N atom of the structure.
Page 9, Problem 1.35(a) The OH bond is more polar, not the C-O bond. The correct structure is CH3O-H, with the partial negative charge on O, and the partial positive charge on H.
Page 24, Problem 1.67(c) The O of H2O changes hybridization in the reaction. I starts as sp2 and turns into the sp2 O atom of the carbonyl.
Page 32, Problem 2.18. The solution is not in the format requested by the problem. The answers should be (a) CH3(CH2)4CH(CH3)2; (b) HC(CH2CH2CH3)3 and (c) CH3C(CH2CH2CH3)2(CH2)4CH3.
Page 33, Problem 2.23(d) The correct formula is C4H8O for this aldehyde. On the top of the next page, the text should read "Compounds (a), (d), and (e) are constitutional isomers. Compounds (c) and (f) represent another set of constitutional isomers. A third set of constitutional isomers is composed of (g) and (h)."
Page 43, Problem 2.45 is accidentally listed as 3.45.
Page 55, problem 3.5. Molecule (4) is different from that listed in the book. This changes the answers to the following:As drawn in the text:
(a) Which represent the same compound?
Molecules (3) and (4) represent the same compound.
(b) Which represent enantiomers?
(1) and (3)/(4) represent a pair of enantiomers.
(c) Which represent a meso compound?
(2) represents a meso compound.
(d) Which are diastereomers?
Pairs of diastereomers: (2) and (1), as well as (2) and (3)/(4).
Page 176, Problem 9.22(a) On the right hand side the product should be HCl, not HBr.
