Textbook: Carey and Giuliano 8th Ed. (2010)

Chapter 7: Stereochemistry

Practice Problems and Mendel Sets

Individual Problems

Problem # 525

On the molecule below, mark each stereocenter with an asterisk. (Note: in some textbooks, stereocenters are referred to as stereogenic centers, chirality centers, or asymmetric centers).

Problem # 526

Assign R or S configuration for each molecule below.

a) is straightforward. I've started you off in b).

Problem # 527

Draw the structure of (2R,3S) 2-bromo-3-chlorobutane using wedges and dashes. Also draw a Fischer projection.

Problem # 528

Indicate which of the molecules below are chiral (if any).

Problem # 319

For a molecule to undergo an E2 reaction, the leaving group and the beta-proton must be in an anti-coplanar conformation (one atom straight up, the other straight down). Based on this, which compound undergoes E2 reaction with KOtBu faster? Why?


Problem # 529

Indicate the major organic product of the reaction below. Include stereochemistry.

Problem # 530


Let's work through anti and syn additions to alkenes.
Show the product for each reaction below, and indicate whether the product will be a racemic mixture of enantiomers, or a meso compound (which is achiral).

Problem # 531


E2 elimination reactions require anti-coplanar geometry. (note: some textbooks call this anti-periplanar).
Let's work through an E2 reaction, and rotate the molecule eblow into an anti-coplanar geometry to predict the product of this E2 reaction.


Problem # 532

Let's work through a chiral resolution. Write out the structure of the indicated compound in each box. Include stereochemistry.

Why is it possible to separate the (R,R) and (R,S) salts?

Problem # 744

After a sample of optically pure (S)-2-ethyl-cyclohexanone is dissolved in an aqueous solution for several hours, a significant loss of optical activity is observed. Explain.

Mendel Sets

MS 906 - Stereochemistry Drills Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 7

Keywords: chiral resolution, Fischer projections, R and S configuration, stereochemistry

Description: This mendel set covers various stereochemistry topics, such as:

  • Assigning R/S configuration
  • Fischer projections
  • Identifying meso molecules
  • Stereoselective reactions (are the products racemic or optically active?)
  • Chiral resolutions

Total Problems: 8