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CH105 - (O) - Tutorial3 (Q) PDF

This document provides a tutorial on organic chemistry concepts including identifying symmetry planes and centers of symmetry to determine if compounds are chiral or achiral. It also covers topics like meso stereoisomers, assigning substituent priority, assigning R/S configurations, drawing 3D representations of chiral molecules, identifying relationships between compounds, assigning configurations like for glycidol, and identifying symmetry elements to determine chirality. The tutorial poses multiple questions on these organic chemistry concepts to test understanding.

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Shivansh Singh
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Download as PDF, TXT or read online on Scribd
56 views

CH105 - (O) - Tutorial3 (Q) PDF

This document provides a tutorial on organic chemistry concepts including identifying symmetry planes and centers of symmetry to determine if compounds are chiral or achiral. It also covers topics like meso stereoisomers, assigning substituent priority, assigning R/S configurations, drawing 3D representations of chiral molecules, identifying relationships between compounds, assigning configurations like for glycidol, and identifying symmetry elements to determine chirality. The tutorial poses multiple questions on these organic chemistry concepts to test understanding.

Uploaded by

Shivansh Singh
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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CH105: Organic Chemistry

Tutorial-3

1. Locate any plane of symmetry or center of symmetry in each one of the


following. Which one is chiral and which one is achiral?

a) (E) –1, 2 –Dichloroethene b) cis –1, 2 –dichlorocyclopropane


c) (Z) –1, 2 –Dichloroethene d) trans –1, 2 –dichlorocyclopropane

2. A meso stereoisomer is possible for one of the following. Which one?

a) 2, 3–dibromopentane b) 2, 4 –dibromopentane
c) 3 –bromo –2 –pentanol d) 4-bromo–2 –pentanol

3. List the substituents in each of the following sets in order of priority from highest to
lowest.

a) -Cl, -OH, -SH, -H b) -CH3, -CH2Br, -CH2Cl, -CH2OH


c) -H, -OH, -CHO, -CH3 d) -CH(CH3)2, -C(CH3)3, -H, -CH=CH2
e) -H, -N(CH3)2, -OCH3, -CH3

4. Assign absolute configurations as R or S and write the Fischer projection for each.

5. Draw three – dimensional representations of,


a) R enantiomer of b) S enantiomer of

H3C Br
O H3C F

H F

6. Determine the absolute configuration of the following chiral molecules

7. Identify the relationship in each of the following pairs as constitutional isomers,


diastereomers, enantiomers or identical.
8. (a) Assign the configuration of glycidol (given below). (b) This optically pure
enantiomer has [] = +12 (neat, without solvent). What would be the measured
rotation of a sample of this compound if it is contaminated by its enantiomer such that
25% of the sample is its enantiomer?

CH2OH
O H

9. Identify all the symmetry elements and comment on whether the following molecules
are chiral or not?

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