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Suggested Reading and Homework. For the sections discussed in class, it is suggested that you complete the problems at the end of each section before moving on to the next section. It’s a good idea to read through the both the reaction summary pages and the glossary at the end of each chapter. The problems at the end of the chapter are more difficult because they usually require understanding several concepts. Doing organic chemistry questions really takes a long time, so work on them well in advance of the exams.
Chapter 7. Structure and Synthesis of Alkenes. Read all sections.
Section 7-7E will not be discussed in class, but Bredt’s
rule is important so you should at least be familiar with its main idea.
Section 7-11B, catalytic dehydrogenation of alkenesalkanes, is useful in a
refinery, but synthetic chemists generally do NOT do this reaction to install
alkenes. Do not propose this reaction on exams as a synthetic method to
selectively introduce a double bond. Some of the questions in chapter 7 require
an understanding of radical chemistry, discussed in Chapter 6.6. Some good end
of chapter questions: 7.28, 7.29,7.40, 7.43, 7.45.
Chapter 8. Reactions of Alkenes. Read all sections. Section 8-16
(polymers) will only be briefly discussed in class, and will not be emphasized
on the exams, but you should be familiar with the concepts. We will probably
come back to the radical chemistry in section 8-3B (along with 6-6) after
covering the other sections. We very briefly discussed olefin metathesis. 8.48c,
8.49, 8.50
Chapter 9. Alkynes. Read all sections. 9.1 – 9.4, study on your own. We briefly discussed structure and acidity (9.5). We looked in detail at formation and reactions of acetylides and addition reactions of alkynes (9.6, 9.7, 9.9 (all subsections), 9.10). 9.8 Self study, and note that some of the reactions were discussed in earlier chapters. 9.40
Chapter 10. Synthesis and Structure of alcohols. Read all sections. We covered in class everything after the introductory sections (10.1 – 10.5), except thiols (10.12). This included making alcohols from additions to carbonyl groups and epoxides.
Chapter 11. Reactions of Alcohols. Read all sections.
Chapter
14.
Ethers, Epoxides and Sulfides. Read all sections. The first 3 sections describe ether
structure, properties and reactivities in good detail, so I recommend you read
these sections. Even if it seems a
little simplistic it will give you a better intuitive understanding of their
reactivity. The remaining sections cover
reactions and concepts that were discussed in class earlier, so this is really
just (a useful) review of many reactions, putting them into one common theme. The new chemistry is in section 14.9, on the
auto-oxidation of ethers. This was only
very briefly mentioned in class. Every
chemist should know how old bottles of ether are safety risks and how they
become potentially explosive. We aren’t going to talk about polymers, but you
might read 14.16 just for curiosity. Review sections 5, 6, 8, 11, 12, 13, 14, 15,
Quiz 1 and
Midterm content stops here.
Chapter 16. Aromatic Compounds.
It’s a good idea to review this chapter if you didn’t take 2273 last
semester because it will help you understand the reactivity of aromatic
compounds (Chapter 17).
Chapter 17. Reactions of Aromatic Compounds.
It’s important that you understand the summary table on page 770. We covered
sections 17.1 – 17.11, 17.15B. We’re
skipping 17.12, but you should be aware of this reaction. We’re skipping 17.13, 17.14 may or may not be
covered. See Chapter 19, sections 19.17 and 19.18.
Chapter 18. Aldehydes and Ketones. I suggest you read the entire chapter. We
really started in a section 18.7 with a review of how aldehydes and ketones are
made, through to the end of the chapter.
Some of this material was covered in earlier sections and was not
reviewed here.
We did not do Chapter 19. Amines. Read on your own, note sections 19.17 and
19.18 were covered when we discussed aromatic chemistry. Most of the lecture material started at
section 19.12. We skipped sections 19.14
– 19.16, and 19.21D.
Chapter 20. Carboxylic Acids. We covered nearly all of the reactions in
this chapter.
Final exam
material stops here.
Chapter 21. Carboxylic
Acid Derivatives. Once you understand the mechanisms associated with
reactions of carboxylic acids and esters, you’ll see that making all sorts of
derivatives involves no new concepts.
So, we went through a lot of reactions making many compounds new to us,
but we did that quickly using this reaction
flow chart. Be sure to study and understand Figure 21-9 as it shows the relative reactivity of carboxylic acid
derivatives. If you understand this
material you should be able to regenerate that chart from memory, including all
the reagents and conditions necessary to effect all the reactions.
Radicals. Radicals were
introduced in 4.2 and 4.3. They return
in 6.6 for
halogenations of alkanes and allyic
bromination, and in 8.3B HBr is added to alkenes
under radical conditions to get opposite regiochemistry to the normal ionic
mechanism.
Chapter 22. Condensations
and Alpha Substitutions of Carbonyl Compounds. I suggest you read the entire chapter. We are skipping sections 22.4 (enamine alkylation), 22.18 (conjugate additions), and 22.19
(Robinson Annulation).
A few exam questions usually come from suggested homework, the textbook or class. They may be exactly the same, or modified.
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