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What is the canonical reference for studying stereochemistry?

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 ...
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2answers
704 views

How does Walter White make pure crystal meth using a non-stereospecific reaction?

In the fantastic TV series Breaking Bad, Walter White, the dying chemistry teacher, takes to making crystal meth (d-methamphetamine) by several routes. Initially, he uses the common small-scale route ...
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152 views

Molecular chirality and optical rotation

Why does having molecular chirality result in optical rotation? The dissymetry or chirality of molecules translates to the rotation of plane polarized light, the magnitude and direction depending on ...
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1answer
445 views

Finding chiral carbons in aromatic or cyclic compounds

I know that for a carbon to be chiral four different groups should be attached to that particular carbon. But, what about in the case of cyclic compounds? What's the method to check chirality if the ...
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1answer
111 views

Racemization of biphenyl compounds

How does the effect of heat and effect of substituents affect racemization of biphenyl compounds?
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0answers
97 views

Entropy and racemization?

The process of racemization of an optically compound is entropy driven and hence nature prefers a racemic mixture to an optically active one, which is consistent with the idea of the intuitive ...
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1answer
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Why is the Wittig reaction syn stereoselective?

This question is meant for a simple (not stabilized) Ylide. Consider the classical mechanism for the Wittig reaction given on Wikipedia I am not able to understand why only one intermediate has ...
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acyclically stereocontrolled reaction: organolithium and 2-chiral compound

Aoyagi et al. (J. Am. Chem. Soc., Vol. 115, No. 24, p 11393) reported that the addition of 2-lithio-1,3-dithiane to the alpha-chiral (S)-2-Acetylpiperidine gives the (2 S,3 S)-configured product. It ...
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132 views

The Evans auxiliary: rotational freedom of the benzyl group - stereoselectivity still guaranteed?

I created the L-Phenylalanine based Evans auxiliary bearing a benzyl group with help of a molecular model set and got into some questions. The structural formula will do: As I suppose a low ...
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1answer
444 views

Effect of periodic acid on cyclohexane derivatives

Periodic acid (per-iodic acid, $\ce{HIO4}$ ) cleaves vicinal diols(to carbonyls) via a cyclic intermediate. Due to the cyclic intermediate, it needs a syn configuration for the $\ce{-OH}$ groups for ...
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973 views

How do I determine the absolute configuration experimentally?

Let's say I synthesized or isolated a chiral molecule and want to know the absolute configuration (R or S) of that molecule. I could obviously solve the structury by X-Ray crystallography, but that's ...
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How do you separate enantiomers?

There are some stereochemical reactions that result in the presence of enantiomers. When moving forward with a practical organic synthesis, how does one usually separate them in order to continue with ...