I am well versed with all the named reactions and all of organic chemistry. I am quite weak in stereochemistry.

What canonical text can I use to study this topic and connect with other parts of the chemistry?


The classical book on stereochemistry is Eliel: Stereochemistry of Organic Compounds, first edition appeared 1962.

You will find overwhelming amount of information there. I would recommend it, regardless your age and level. It is so well written, that it is worth at least of fast reading over most important parts. You should find it in any reasonable library, no need to get the latest edition, even the older ones should cover what you need.


Start here. Now, the fun stuff off-syllabus.

It is possible to create chiral centers - including planar chiral centers - whose handedness cannot be named, even in principle, e.g., $\ce{CR4}$ and $\ce{R2>C=C<R2}$. The pictured acyclic carbons are chiral centers. Show their non-superposable enantiomers that illustrate the anomaly. (Answer to be posted end of the week - though you already know it, but may not know you know it.)

Optical rotation is not a measure of chirality, or even an indication of chirality. Solution optical rotations ignore atomic mass distribution[1]. Silver thiogallate, $\ce{AgGaS2}$ in achiral space group ${I}$-42${d}$, rotates 522°/mm along [100] at 497.4 nm[2]. ${P3_121}$ quartz and ${P3_221}$ berlinite, with opposite sense three-fold screw axes ($3_1$ right-handed, $3_2$ left-handed), are both levorotatory[3]. CIP notation flips with composition at constant geometry (L-cysteine versus most other L-amino acids).

[1] http://www.mazepath.com/uncleal/norbors.gif
[2] Appl. Cryst. 33, 126 (2000)
[3] J. Appl. Crystallogr. 19, 108 (1986)

J. Math. Phys. 40, 4587 (1999)
Quantitative geometric chirality can be calculated in any number of dimensions for any collection of a countable number of anonymous points with overall finite principle moments of inertia. Mathematically perfectly chiral arrays are rotationally symmetric but lacking all ${S_n}$ improper rotation axes.

  • $\begingroup$ The enantiomer of CR4 is CS4 (Cahn-Ingold-Prelog notation). A chiral substituent may not be cut by a mirror plane. R and S reflect or invert as S and R respectively, so those are not allowed symmetries. We thus see two planar chiral centers in the olefin. It is nice as a test extra credit question. $\endgroup$
    – Uncle Al
    Mar 14 '14 at 1:31

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