Organic Chemistry Laboratory Manual

Name: _______________________________ Date Performed: _______________

Groupmate: ___________________________ Section: ______________________

EXPERIMENT 5. ISOMERISM AND STEREOCHEMISTRY

I. Newman projections of the different conformational isomers of butane

Most stable: _____ Why? ______________________________________________

Least stable: _____ Why? ______________________________________________

II. C2H4BrCl

1. Structural isomers of C2H4BrCl

Newman projection of the most stable conformational isomer (indicate absolute

configuration)

2. Newman projection of the mirror image (indicate absolute configuration).

Is this superimposable to the model in 1? How are these two compounds related?

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman

Organic Chemistry Laboratory Manual

III. Methylcyclohexane

1. Newman projection of methylcyclohexane chair conformation

Position of the methyl group: ____________________

2. Newman projection of the other chair form of methylcyclohexane

Position of the methyl group: ____________________

More stable of the two chair conformation: _______ Why? __________________

3. Newman projection of the boat form

Which is more stable, the chair or the boat? ___________ Why? _______________

IV. Newman projection of the mirror images of trans-1,3-dimethylcyclohexane

Are they superimposable?

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman

Organic Chemistry Laboratory Manual

V. Newman projection of isomers of CH3-CHOH-CHOH-CHO (indicate absolute configuration of

chiral centers)

Number of chiral centers of each isomer: ___________

Which are enantiomers? ___________
Which are diastereomers? ___________

VI. Newman projection of stereoisomers of CH3-CHOH-CHOH-CH3 (indicate absolute

configuration of chiral centers)

Number of chiral centers of each isomer: ___________

Which are enantiomers? ___________
Which are diastereomers? ___________
Is there any meso compound present? ___________

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman