© 2001 Rainer Glaser.
The University of Missouri at Columbia
Chemistry 210 - Honors Organic Chemistry I - FS01


Recommended Problems

Always work the in-chapter problems at the time you learn the material. Work these problems with the book open. Working these problems serves to enhance your reading-comprehension of the chapter.

Try to solve the "study problems" without going back to the respective pages in the book! If you cannot solve the problem in this way, then go back to reading the respective chapter. Then try the problem again. ... Do not solve the problems with the solution manual open! The solution manual merely should provide a check as to whether your answers are correct.

Problems to go with Wade, 4/e and Carey, 4/e.


CHAPTER 1
1.19-1.40
We will get into acidities and basicities as we study functional group chemistry.


Uebung macht den Meister!

CHAPTER 2
2.22-23
Skip 2.24, we will talk about ring strain later.
2.25-28 are important problems.
2.29
Skip 2.30, we will deal with conformations of cyclic systems later.
2.31
Skip 2.32-33, we will learn cis/trans isomers later.
2.34-36 are good ones!
2.37-39 to exercise H-bonding
and that will be all.


Der Morgen ist die schoenste und schicklichste Zeit zur Arbeit, weil wir dann verjuengt, biegsamer, kraeftiger, von groesster natuerlicher Reizsamkeit sind, kurz, mehr jugendliche Wesensart aufweisen.

CHAPTER 3
3.32-39
3.40 is about intermolecular interactions
3.41 Skip this one! Know the propyls & butyls, and that will do.
3.42-45 deal with cyclohexanes (Wednesday lecture).
3.46 Skip this one!


Was Du heute kannst besorgen, das verschiebe nicht auf morgen!

CHAPTER 4
In general, we are focusing on radicals in chapter 4. Wade talks quite a bit about carbenium ions as well; we will discuss carbenium ions in detail in chapter 6 and not now.
4.32 with clear focus on radicals.
4.33-35 to exercise potential energy diagrams.
4.36 will be dealt with in chapter 6.
4.37 is something you should know already (chapter 3).
4.38 & 4.39 to learn about homolytic bond dissociation energies.
4.40-44 to review the mechanism of alkane chlorination and selectivity.
4.45&46 to review the formation of mixtures.
4.47-51 skip these.
4.52 is a good one. Take a good look at this problem!

Wenn Du es eilig hast, gehe langsam!

CHAPTER 5
5.26
5.27-28 feel free to use models to decide about symmetry elements
5.29-31 to exercise Fischer projections
5.32 just decide whether the structures are chiral or not
5.33-34 and 5.36 to exercise the calculation of optical rotations
Skip 5.35 and 5.37-5.39


Morgen, morgen nur nicht heute, sagen alle faulen Leute.

CHAPTER 6
6.49-51 Terms and nomenclature
6.52-54 on SN reactions
Skip 6.55
6.56-58 on kinetics of SN reactions
6.59-62 on carbocations and rearrangements
6.63-64 on SN reactions and stereochemistry
Skip 6.68 and 6.69
6.65-67 and 6.70-71 on Eliminations
That is it for now. I might add a few more on 10/15.


Ohne Schweiss, kein Preis

CHAPTER 7
7.19-22 Terms and nomenclature
7.23-24 Skip.
7.25-26 More nomenclature and properties
7.27-28 Sayzeff rules!
7.29-30 Synthesis!
7.31 Retrosynthesis!
7.33-34 More synthesis!
7.35-40 Skip them all.
7.41 This was dealt with in lecture.
7.42-44 Skip them all.


Wo ein Wille ist, ist auch ein Weg.

CHAPTER 8
8.43 Terms and nomenclature
8.44-47 Synthesis
8.48-51 Skip these for now. Polymers will be dealt with in Chem 212!
8.52-54 Mechanism.
8.55-56 More Synthesis
8.57-61 Skip them all!
8.62 This is a nice one
8.63 This is a good one
8.64-8.69 Skip them all!


Wer den Kern essen will, muss die Nuss knacken.

CHAPTER 9
9.26-29 Terms and nomenclature
9.30-31 Skip these
9.32 Stereochemistry of hydrogenation
9.33-34 Synthesis
9.35 Synthesis, Route Map
9.36 Synthesis
9.37 Synthesis, Retrosynthesis
9.38-39 Ozonolysis


Der Misserfolg ist die Mutter des Erfolgs. (German)
Shippai ha Seikou no Haha. (Japanese)


CHAPTER 10
10.30-33 Terms and nomenclature
10.34-36 and 10.42 Properties and H-bonding
10.37-41 Reactions and Synthesis.

Voller Bauch studiert nicht gern!

CHAPTER 11
11.38 Terms and nomenclature
11.39-45 Reactions and Synthesis
11.46 Mechanism
11.47 Retrosynthesis
11.48 Reactions
11.49 Test Reactions

Es ist noch kein Meister vom Himmel gefallen!

CHAPTER 13
13.33 Signal integration
13.34 Splitting pattern
13.35 Chemical shift prediction
13.36+38 Spectrum interpretation
13.39 Spectrum prediction
13.40 Comparative analysis
13.41-42 Carbon spectra

Erst die Arbeit, dann das Vergnuegen.


Problems to CHAPTERS 1 & 2 of Notes are located in CHAPTER 1 of Carey, 4e
1.23 - 1.29 Lewis structures and formal charges
1.30 One of my favorite problems!
1.31 is much like 1.30
1.32 - 1.35 More Lewis structures
1.36 - 1.39 Isomeric structures (comes later in more detail)
1.40 - 1.41 Dipole Moment
1.42 Drop
1.43 Condensed structural formulas
1.44 Drop.
1.45 - 1.48 Hybridization & MOs


Uebung macht den Meister!

Problems to CHAPTERS 3 of Notes are located in CHAPTER 2 of Carey, 4e
2.16 Don't do it. Nothing to be learned by this.
2.17 Don't do this.
2.18 - 2.21 Nomenclature.
2.23 Drop this one.
2.24 Recognize isomers.
2.25 - 2.32 Drop these ones.
2.33 - 2.35 Combustion of Alkanes.
2.36 - 2.45 Drop these ones.


Der Morgen ist die schoenste und schicklichste Zeit zur Arbeit, weil wir dann verjuengt, biegsamer, kraeftiger, von groesster natuerlicher Reizsamkeit sind, kurz, mehr jugendliche Wesensart aufweisen.

Problems to CHAPTERS 3 of Notes on "Conformations of Molecules" are located in CHAPTER 3 of Carey, 4e
3.15 Good one.
3.16 See lecture.
3.17 & 3.18 Good ones.
3.19 Good one. 3.20 & 3.21 Skip.
3.22 It's drawn eclipsed! Next.
3.23 Easy!
3.24 Skip.
3.25 We'll talk about that later!!
3.26 Skip.
3.27 Do.
3.28 - 3.30 We'll deal with this later!!
3.31 & 3.32 Build models!
Skip all the rest!


Was Du heute kannst besorgen, das verschiebe nicht auf morgen!

Problems to CHAPTERS 4 of Notes on "Halogenations of Alkanes" are located in CHAPTER 4 of Carey, 4e
4.38 & 4.44 Mechanism!
4.39 Regiochemistry!
4.40 Talk about these options in your study group!
4.41 - 4.43 Regiochemistry and Selectivity


Wenn Du es eilig hast, gehe langsam!

Problems to CHAPTERS 5 of Notes on "Stereochemistry" are located in CHAPTER 7 of Carey, 4e
7.23 A good one. Use models!
7.24 & 7.25 Take a quick look.
7.26 A good one!
7.27 Skip. We know that by now!
7.28 This is a good one!
7.29 Do this one in your group and keep score!
7.30 - 7.35 Skip them all!
7.36 - 7.38 Optical active or not?
7.39 - 7.49 Skip. We will do alkene chemistry later.


Morgen, morgen nur nicht heute, sagen alle faulen Leute.

Problems to CHAPTER 6 of Notes on "Alkyl Halides" are located in CHAPTERS 8 (SN) and 5 (E) of Carey, 4e
8.17, 8.19 & 8.20 VERY important. Know your reaction products!
8.18 SN vs E.
8.19 Skip.
8.22 & 8.24 Substrate dependence of SN.
8.23 Leaving group. 8.25 Skip thiocyanates.
8.26 - 8.28 More reactions.
8.29 Skip.
8.30 & 8.31 Synthesis of nitriles, iodides, azides and ethers.
8.33 - 8.35 Doing SN reactions with alcohols via inorganic esters.
8.36 A classic!
8.37 - 8.38 Do these later (needs alcohol chemistry)
8.39 - 8.41 Solvolysis.
That will do it for now. The problems on elimination reactions are given in Chapter 5 starting with problem 5.30 (vide infra).

Ohne Schweiss, kein Preis

Problems to CHAPTER 7 of Notes on "Alkenes" are located in CHAPTER 5 of Carey, 4e
5.21 & 5.23 Nomenclature
5.22 & 5.24 Skip.
5.25 Do one or two of these problems in your groups!
5.26 Good one
5.27 - 5.29 Alkene Stability
The following problems deal with elimination reactions to form alkenes.
5.30 Recognize your beta-hydrogens!
5.31 Regiochemistry: Saytzeff vs Hoffman
5.32 - 5.35 Skip!
5.36 Do them all!
5.37 - 5.38 Mechanisms.
5.39 A good one!
5.41 - 5.45 Rearrangements!
5.46 & 5.47 Skip.


Wo ein Wille ist, ist auch ein Weg.

Problems to CHAPTER 8 of Notes on "Reactions of Alkenes" are located in CHAPTER 6 of Carey, 4e
6.22 - 6.24 Excellent exercises.
6.25 Review of alkene stability.
6.26 & 6.27 Skip.
6.28 A good one.
6.29 Skip.
6.30 A good one.
6.31 A good one.
6.32 Do this one in your group.
6.33 Skip.
6.34 - 6.38 Hydrogenation.
6.39 Good problem.
That will do for now.


Wer den Kern essen will, muss die Nuss knacken.