U1P7-Exercises - Unit 1 Exercise PDF

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Unit 1 Exercise...

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Unit 1 Part 7 – Stereochemistry Exercise 1 1.

Draw the two chair conformations of cis-1,3-dimethylcyclohexane. Is one more stable than the other? If so, explain why.

2.

Draw the most stable chair conformation of menthol:

Exercise 2 Draw all the stereoisomers of the following molecules 1.

CH3CHOHCH2CH3

2.

BrCHCHCH3

3.

Mark all the stereocentres in the thalidomide molecule.

Draw the pair of stereoisomers and label them diastereomers or enantiomers where appropriate: 4.

CH3CH2CHCHCl

5.

CH3CH(OH)CH2CH2Cl

6.

(CH3CH2)2CHCHCHCH2Cl

Draw a structural formula for each of the following compounds and indicate clearly which atoms are stereocentres. (Hint: The symbol Ph represents a C6H5 ring substituent, usually called the phenyl ring.) 7.

CH3CHClF

8.

PhCH(NO2)CH3

9.

CH2(OH)CH(OH)CH(OH)COOH

10.

Menthol, extracted from peppermint oil, has three stereocentres yet only the stereoisomer shown occurs. How many other stereoisomers are possible?

11.

Draw all the possible isomers of CH3CH(OH)CHCHCH3. Label each pair of molecules as enantiomers or diastereomers.

12.

The compound 1,3-dimethylcyclohexane can exist as cis or trans isomers. Draw both, and then draw the structures that illustrate the the chair conformations of both the cis and the trans. Which conformation would you expect to be most stable?...