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PROBLEM 10.45

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Organic Chemistry
Found in: Page 421

Short Answer

Question: Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China.

(a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid.

(b) Draw the structure of a stereoisomer that has a lower melting point.

Answer

a.Higher melting point:

b.Lower melting point:

See the step by step solution

Step by Step Solution

Stereoisomers

The molecules have a difference in the orientation of atoms but have the same composition.

Enantiomers and diastereomers are the two types of stereoisomers present.

Structure of Eleostearic Acid

The structure of eleostearic acid is shown below:

Structure of Eleostearic Acid

The two isomers of Eleostearic Acid can be represented as shown below:

Structure of cis-eleostearic acid

Structure of trans-eleostearic acid

Stereoisomer with a higher and lower melting point

The stereoisomer with a higher melting point than eleostearic acid is trans-eleostearic acid, as all the bonds in this molecule are in a trans-position.

In the trans configuration, the extent of hydrogenation is more, and the fatty acids are packed relatively well as they have rod-like shapes.

The stereoisomer with a lower melting point than eleostearic acid is cis- eleostearic acid, as all the bonds in this molecule is in a cis position.

In the cis configuration, the van der Waals force of attraction between the molecules decreases as there is a bend in the structure.

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