Question

A. Consider the following pairs of structures. Designate each chirality center as (R) or (S) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers.

а. and CI b. CI and CI CI с. CI and CI CId. Н,Си Br and Br е. Hас, F Br and CHз Br н f. H CH3 Н.С H and +$ti||| Br Br F CH3 Br CH3 Br H H. and H3C F FI CH3 H LL I Ih. Br H .CH3 НаС. Br and F CH3 H Fu CH3 н i. Br CH3 H Нс CH3 H and F F Н,С Br H H H j. CHз Br Hас, lto and CH3 Br H CH3 k. CHCH3 CH3 H Br CI н and H CI Br H CH3 CHз Br m. H Br С—С—С- С—С—С: and Br н H Br n. and O. andp. Cl C/ and CI CI CI CI and CI CI ll. CI CI

B.  Tartaric acid [HO2CCH(OH)CH(OH)CO2H] was an important compound in the history of stereochemistry. Two naturally occurring forms of tartaric acid are optically inactive. One optically inactive form has a melting point of 210 − 212 ° C , the other a melting point of 140 ° C . The inactive tartaric acid with a melting point of 210 − 212 ° C can be separated into two optically active forms of tartaric acid with the same melting point ( 168 − 170 ° C ). One optically active tartaric acid has α D 25 = + 12 , and the other, α D 25 = − 12 . All attempts to separate the other inactive tartaric acid (melting point 140 ° C ) into optically active compounds fail.

  1. Write the three-dimensional structure of the tartaric acid with melting point 140 ° C .
  2. Write structures for the optically active tartaric acids with melting points of 168 − 170 ° C .
  3. Can you determine from the formulas which tartaric acid in (b) has a positive rotation and which has a negative rotation?
  4. What is the nature of the form of tartaric acid with a melting point of 210 − 212 ° C ?
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Answer #1

citats @ ce -ave to ce 18 - cé IR dp- 15 - 38 - IR > BR Entiomers . Entismens CHIC BY T O Br Com (2,52 D | Identical species19 CM By Br p or. Brin ant Br ta Br term (S) (identical) Ce Jl . species af 18 - IR - 28 Diasteromers) che Br - Br of Br 17230..BY ,CM3 e Criz cob 19 ds --18 POR (Diasteromeus) (constitutional isomers) nt cette at 10 TP مو مو (Diastenomens) Cris C@ =e- cimbro Spy - K (8) As 4th Benarity above the piane Identical species) anice Diastero mere). (Geometrical isomers) @ Ide

Identical Species: - when configuration on all the carbon atoms is same in both species.

Entiomers:- when configuration on all the carbon atoms is different in both species.

Daisteromers:- when configuration at least one carbon atom is same and at others is diffferent.

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