Stereochemical Assignment Notebook

All assignments in Klein, Organic Chemistry, 2nd Edition.

I strongly recommend keeping a separate section in your notebook for the homework assignments.

  • After you have solved a problem working on scratch paper, make a reasonably neat copy for the notebook.
  • Also include a note about any new ideas or techniques you used to solve the problem, or references to text or web pages where you found help, so that you can review these things prior to an examination.
  • If you just can't get the answer, make a note about that and come to me for help!

You will note that the problems at the ends of the chapters are keyed to the chapter section in which the related ideas occur.

  • Work the appropriate problems as your finish reading the relevant chapter section.
  • Then move on to the next section, followed by its problems, and so on.

I will post here a few example solutions of problems. The Study Guide/Solutions Manual also provides reasonably good descriptions of how to solve the problems.

Chapter 1

  • Problems 1.34 - 1.36, 1.38, 1.39, 1.41 - 1.43, 1.46, 1.47, 1.49, 1.50, 1.53, 1.55, 1.57, 1.59, 1.63, 1.72, 1.75, 1.77. Use my rules (below) for drawing Lewis structures.

    Here's a little extra help with writing resonance structures:

  • Also work the supplementary problems found here:
 

Chapter 2

  • Problems 2.39 - 2.51, 2.54, 2.55, 2.57, 2.58, 2.63, 2.67, 2.71, 2.73
  • Also work the supplementary problems found here:
Chapter 3
  • Problems 3.36 - 3.40, 3.43 -3.47, 3.49, 3.51, 3.52, 3.54, 3.55, 3.59, 3.62

Chapter 4

  • 4.39 - 4.43, 4.45 - 4.48, 4.51, 4.53 - 4.57, 4.59, 4.60, 4.62, 4.63, 4.65, 4.66, 4.68, 4.69, 4.76
  • Alkyl groups can be given either trivial or systematic names; here's a comparison:
  • Also work the supplementary problem here:

Chapter 5:

I urge you to work the Chapter 5 problems with your models in hand! Build the stereoisomers. Convince yourself that they cannot be superposed. Seeing molecules in three dimensions is one of the hardest things we do; make use of every resource to help.

Do NOT use Haworth projections in working these problems. You will get wrong answers. For example, cis-1,2-dimethylcyclohexane IS chiral!

  • 5.32, 5.33, 5.35 - 5.37, 5.39, 5.42, 5.45, 5.46, 5.48, 5.49 (not parts b, k, or l), 5.51, 5.53, 5.58 - 5.60

Chapter 15

  • 15.38 - 15.42, 15.44, 15.47. 15.54, 15.55, 15.57
  • Also work the supplementary problems here:

Chapter 16

  • 16.31, 16.32, 16.35 - 16.41, 16.44, 16.46, 16.48, 16.51 - 16.53, 16.55 - 16.57, 16,62, 16.63, 16.65

Chapter 6

  • 6.21, 6.22, 6.25 - 6.28, 6.30, 6.33, 6.35, 6.37, 6.39, 6.41 - 6.47, 6.55, 6.60

Chapter 7

  • 7.37 - 7.41, 7.44, 7.45, 7.47 - 7.53, 7.55, 7.58 - 7.60, 7.62, 7.63, 7.65, 7.67, 7.69

Chapter 8

  • 8.50, 8.54, 8.56, 8.59 - 8.69, 8.72 - 8.76, 8.79, 8.83, 8.84

Supplementary problems for Chapters 7 and 8, below:

Chapter 9

  • 9.49 - 9.55, 9.57, 9.58, 9.60, 9.62 - 9.65, 9.69 - 9.71, 9.80,

Assignments below this line are not up to date.


Chapter 10

  • Section 10.3 Nomenclature and Stereochemistry: 10.39 - 10.41
  • Sections 10.8-14.14 REactions of Alkenes: 10.52 - 10.56, 10.58 - 10.60, 10.63, 10.65 - 10.67, 10.71
  • Section 10.17, 10.18 Synthesis: 10.72 - 10.75

Sections below not up to date yet.

Chapter 11

Problems: 11.25, 11.27 - 11.33, 11.35 - 11.40, 11.43, 11.45 - 11.47, 11.49 - 11.53, 11.57

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