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Synthesis of Phenols II

41. Identify ...

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41. Identify product when (R)- and (S)-2-butanol reacts with (RR) tartaric acid in acidicmedium(a) Racemic(c) Meso(b) Diastereomer(d) Pure enantiomer

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Q. Identify product when

(R) -

(S) - 2 -

butanol reacts with

(R, R)

tartaric acid in acidic medium.

Pure enantiomeric acid + optically active alcohol having chiral C atom $\to$ ?

A schematic analysis of the reaction of one enantiomer with racemic mixture is shown below

\begin{matrix} d & + & d a n d l & \to & (d) - (d) T h e (+) f o r m o f & A r a c e m i c m i x t u r e o f & + c h i r a l m o l e c u l e s & o t h e r m o l e c u l e s w i t h & (d) - (l) 50 % (d) a n d 50 % (l) \end{matrix}

The products (d-d) and (d-l) are clearly neither identical nor enantiomers (non-superimposable mirror images) as the mirror image of (d-d) is (l-l) not (d-l). They are diastereomers, 'stereoisomers that are not mirror images'.

The formation of diastereomers allows the separation of enantiomers (called resolution) which is not easy as enantiomers have identical physical properties. One general procedure for separating enantiomers is to allow them to react with naturally occurring chiral molecule to form a pair of diastereomers. These can be separated easily as they have different physical properties. if the original chemical reaction can be reversed, the enantiomers can be isolated.

Which of the following is an example of diastereomers?

How to identify diastereomers and enantiomers?

Q. An enantiomerically pure acid is treated with racemic mixture of an alcohol having chiral carbon, the ester formed will be:

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Synthesis of Phenols II

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