Study Guide Errors

You may have noticed a stunning similarity between the name of one of the authors who wrote the text book Study Guide we are using and my name. In fact, my wife and I wrote the study guide. Unfortunately, depending on which printing of the study guide you have, there are still some mistakes in it. We will post them 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 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:

I know this doesn't count in your SG error hunt, but since you know the author, I figured you could tell him for the next edition. On page 39, Figure 1.20 (c) of the sp hybrid orbitals, the second py orbital should be blue, I think, to signfiy that it is negative rather than positive. It's really not a big error, but the book has been coloring it blue in previous illustrations, so I just thought the author might like to know.

You are absolutely correct! I will E-mail the author immediately!

In the solution to problem 1.18(b), why doesn't the study guide show the other
hydrogen attached to the nitrogen in both the ball and stick model and the
space-filling model?

I took a bad angle for printing the molecule, as the missing hydrogen atom is perfectly behind the nitrogen atom in this view. Thanks for pointing this out!

For 1.35 part (a) of the SG it has CH3-OH or CH3O-H, but in the text book it has
(a) CH3-OH or CH3O-OH. The alcohol is not written in the SG for the second
part. Also, in part (d) the textbook has CH3-F or H-H, but the study guide
lists the H-H as H-F. The two do not correspond; I think that is an error by
the textbook.

Nice job. These must have been changed after I saw the problems from the book. I will pay up for these, even though they are likely the printer's fault. Come see me before class today!

On problem 1.55(e) the question asks for the orbital hybridization
of the highlighted atom, however in the solutions manual you show two
answers, which is slightly confusing since the problem only asked about
one atom. It's not a major mistake but we just thought you'd like to
know. See you in class!

Good eyes! In fact, another student has pointed this out. It turns out to be a problem with the textbook (not study guide) printing, as the galley proofs were correct. Thanks! Keep looking!

I was wondering on HW problem #1.70 c, doesn't the hybridization of oxygen change from sp3 to sp2? This is not pointed out in the answer guide, and I was wondering if I was correct on this assumption or not.

Yes, you are correct. I guess it wasn't pointed out because the water was not drawn in a way that made me notice it. I will fix it for the next version. Thanks.

In the book, problem 2.16 part (b) asks to put in order 2,2,4-trimethylhexane along with two other alkanes according to their boiling points.  But in the study guide on page 31, 2,2,4,4-tetramethylpentane is written instead. 

The problem was changed somewhere before the book was printed and I was unaware of the change. However, the answer in the Study Guide is still correct once you substitute the 2,2,4-trimethylhexane for 2,2,4,4-tetramethylpentane in the relative order of boiling points. In either case, more branching means less surface area so less attraction between molecules and a lower boiling point.

Problem 2.31 should be "As can be seen, the equatorial hydrogen from the carbon atom in the front...", instead of "axial?" The reason is that the given Newman projections show the equatorial (not axial) H atom of the front C is in between the equatorial and axial H atoms of the rear C.

Correct, it should say the equatorial H atom not the axial H atom.

I found a small error in the study guide that I didn't
see on the website page, so I thought I'd point it out. On page 48,
problem 3.2, you list part (c) as part (a). The answers are right, but
it's a little confusing at first.

Wow. You have great eyes to see that one!

Onproblem 3.19 in the textbook, it asks us to assign priorities to the groups they listed. On part d of 3.19, they list -CH3, -CH2SH, -NH3+, -CHO. In the study guide, the answer has -COO instead of -CHO. I don't think that is a major error, but it confused me at first when I saw the misprint. I just thought I would point out this misprint. If someone else has already done so, then please excuse this submission.

This is another one of those in which something changed when the book was printed. The good news is that if you substitute CHO for COO- in the answer, you get the same order. Thanks for pointing this out.

On number 3.25 part f, in the book the drawing does not have a vertical branch
on the first carbon coming off of the six-membered ring, but in the study
guide, it does. And in the study guide, this carbon is shown as a stereocenter.
Because there is no branch coming off of it in the book, doesn't that mean that
in fact it is not a stereocenter?

I am afraid the true molecule has a branch, it was left off the structure by the printers. The answer in the study guide is correct, and there is a stereocenter there.

In the textbook, problem 4.1 part (c) asks for CH3OH, CH3O- and in the study guide part
(c) gives CH3OH, CH3OH2+

Yikes, thanks for bringing this to my attention. I owe you some money!

On part (g) CH3S-, CH3SH... In the Lewis Dot structures for the pair each have CH3CH2 (ethyl) attached to the Sulfur, rather than just the CH3 (methyl).

You are correct, they should be methyl groups.

For problem 4.39 the CH3COO-(minus) molecule is circled but the structure for HCO3- is what is drawn. The problem in the book ask for us to select the strongest base and then draw its structure. So which one is correct?
Roberto

It turns out that acetic acid is the stronger acid, so carbonic acid is the weaker acid (Table 4.1) As a result, the bicarbonate anion (the one drawn) is the stronger base. The circle should be moved to the the bicarbonate anion.

I think I found a mistake in the solutions manual. On page 84, problem 5.9, the parts (a), (b), and (c) are in a different order and/or are slightly different than in the book (pg. 175). I know it's tivial, but I just thought you might want to know.

Thanks, the problem must have been changed after I saw the book manuscript.

On 6.17, you say that f has only one sterocenter, but it has two. Also, h is not listed.


You are correct about the number of stereocenters in f , and H should be listed as being racemic, since there is a stereocenter created.

Question (a) of 6.14 shows only one Bond dissociation energy for the two molecules of hydrogen. Since two h-h bonds are being broken in the reaction (on the reactant side), should this number be multiplied by two because of the coefficient?

You are absolutely correct!! I owe you some money! The total for the left side of the question is supposed to be 4083 kJ/mol, not the 3648 kJ/mol currently listed.

It looks like there is a stereocenter in 6.43 a). Look at the carbon of the vertical line near the hydroxide group after the reduction. Shouldn't it be racemic?

You are absolutely correct! I owe you some money.

In the textbook problem 7.2, it ask you to give all monochlorination products formed when 2-methylpropane is treated with Cl2. In the study guide you answer the question with butane treated with Cl2. Just wanted to let you of the difference in the problem.

Thanks, I owe you some money. The author made some last minute changes in the book and I didn't catch them all.. Great job!

problem 8.1 (part c)...In the book the reaction involves Li+, but in the SG it says Na+.

Good eyes, we messed up.

This is very very minor, but on problem 8.12 part (e) in the book there's Li+ attached to the alkyne, where as in the answer key it's labeled as Na+. I know the answer is the same regardless, but just thought I'd mention it.

Thanks! I truly appreciate you taking the time to E-mail, as I can read the answers one hundred times and these kind of things always slip through.

I think that there is a possible mistake in manual. On Problem 8.7 (pg 142solutions manual top of the page), for the products of the trans: should the wedges have (CH3)2CH attached instead of (CH3)3C to the wedges?

You are absolutely correct! The group attached to the ring should be CH(CH3)2, not C(CH3)3. I owe you some money!

I was looking over some old homework problems and on number 7.24(a) in the study guide, there are four hydrogens instead of three on the first carbon of 2-pentene (in the first part of the explanation). It kinda confused me for a second, so I just wanted to let you know about it.

Yikes, you are correct!!! I owe you some money!

On pg. 159, question 8.44, part c, the study guide shows 5 carbons, but the problem in the book only shows 4. Just a detail but thought I'd let you know in case it hadn't been caught yet.

No I had not seen this one. Great job.

On problem 9.15, why would part (f) be named (R)-3-hydroxy-1-butanol while part (i) is named 2,3-butanediol?
Is "hydroxyl" common nomenclature?

I hadn't caught that one. Part (f) should be 3(R)-1,3-butanediol. Thanks!

Questions 9.41 and 9.42 are switched in the solutions manual.

Thanks. You are correct. I owe you some money!

On problem 10.8 part g there is a 6 carbon chain so why is it named pentyne? I just thought that was odd but maybe I don't know all the nomenclature rules myself and so try not to laugh too hard if I'm wrong.

You are correct. Fear not, even if you were wrong, I would never laugh. There is no humor in nomenclature!

I think there is a mistake on question 10.20 part C. The enol is suppose to be CH2 at the far right end instead of CH3, which would make the C to have five instead of four bonds. Hope this is correct!

You are absolutely correct. Great job! I owe you some money.

On page 240 of the solutions manual, Problem 13.2 (a) shouldnt' it say Set c: 3 hydrogens from teh methyl group of carbon atom 6 instead of 5.

You are correct. I owe you two dollars. Come see me before class tomorrow!

16.15A. The name is given as 4-nonanone, but I have counted from both directions of the molecule and that carbonyl group is definitely on the 5th carbon from either direction.

Correct! The molecule is 5-nonanone, not 4-nonanone. I owe you some money.

I'm not sure if this is a mistake, but on page 273 in the study guide, one part of the question (15.4) is to show how to get each epoxide from the appropriate alkene, but I don't see that in the guide. I only see the first part of the question on how to get each Gilman reagent from the appropriate alkyl halide.

The epoxides should have been there. They are constructed from the appropriate alkenes (1-pentene, and 4-phenyl-1-butene) and a peracid such as peroxyacetic acid or meta-chloroperoxybenzoic acid (pg. 406 of the text).

On page 273 again, 15.5 part (a) has iodobenzene as a starting material and then in the products we have the benzene ring with a methyl group attached at the top. Should that starting material also have that methyl group before the Heck reaction even takes place?

Good eyes, there most certainly should be a methyl group on the starting material. The methyl group should be right next to the iodine atom.

Hi. I am not sure if this is an error or not, but on the bottom of page 294 of the study guide, for problem 16.21 there is 3-Hexanol that is treated with SOCl2 and Mg, ether to give a Grignard reagent. Afterwards there is MgBr attached to where the OH was before, I was just wondering if it should be a MgCl there instead of the MgBr since we use SOCl2.

You are correct. I owe you some money!