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Tutorial 2

This document provides tutorial questions on organic chemistry concepts including stereochemistry, reaction mechanisms, isomerism, and resonance structures. Students are asked to draw structural representations of organic molecules including Newman projections and skeletal structures, identify chiral centers and assign R/S configurations, determine the number of possible stereoisomers, illustrate reaction curly arrows and complete reaction schemes, and analyze energy diagrams of reaction mechanisms.

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Joshua Lopez
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63 views5 pages

Tutorial 2

This document provides tutorial questions on organic chemistry concepts including stereochemistry, reaction mechanisms, isomerism, and resonance structures. Students are asked to draw structural representations of organic molecules including Newman projections and skeletal structures, identify chiral centers and assign R/S configurations, determine the number of possible stereoisomers, illustrate reaction curly arrows and complete reaction schemes, and analyze energy diagrams of reaction mechanisms.

Uploaded by

Joshua Lopez
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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School of Physical & Mathematical Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 2 Stereochemistry and Reaction Mechanism 1) Sighting along C2-C1 axis, draw the Newman projections of the most stable conformation for the following compounds:
1 1 2

F
2 1 2

H3C

Br

HO H

CH3

Do the same as the above but sight along C1-C2 axis.

2) Draw the skeletal structures for the following Newman projections (Me is CH3, Et is CH2CH3):
H Me OH H H H Me OH Et H H Me ClMe H OH

Me

OH

School of Physical & Mathematical Sciences


Division of Chemistry & Biological Chemistry

3) For each of the compounds below, draw the 2 chair conformations:


2 1 4 5 2 1 4

Et H

H Me

HO

For the 2 skeletal structures above, draw the 2 Newman projections of the 2 chair conformations by sighting along both C1-C2 and C5-C4.

4) How many stereoisomers are possible for the following compounds?


O HO

OH

Cl

OH

5) Determine the R/S configuration for all the chiral centres present in the following compounds:
Cl H3C Br CH3O H O OH Ph Br HO OH CH3 CH3 H3C H Br H CH3

Br

Which compound is achiral?

School of Physical & Mathematical Sciences


Division of Chemistry & Biological Chemistry

6) List out all the isomers of C4H7Cl. Identify the pairs of enantiomers and diastereomers.

School of Physical & Mathematical Sciences


Division of Chemistry & Biological Chemistry

7) Fill in the curved arrows or the missing products for the following one-step reactions:
O H O O H O O H

I H O

HO

OH

2 HO

+
O

Br

HO

Br

O CH2

CH2

H O

+
Br

Br

O H

CH3 O O H O

CH3

HO

OH N N

OH

CO2CH3 H3C S H 3C S

CO2CH3

School of Physical & Mathematical Sciences


Division of Chemistry & Biological Chemistry

8) Draw as many resonance structures as possible for the following compounds. Show the movement of electrons using curved arrows.
H2N NH2 H2N H H H NH2 C N

9) Compound A is converted to compound G and the energy diagram is as shown:

Energy

Reaction progress

a) b) c) d)

Which are the intermediates and which are the transition states? How many steps are there in the reaction mechanism? Is the reaction exergonic or endergonic? How would the rate of reaction be affected if A is made less stable without affecting the energy of the rest of the intermediates and product? e) How would Keq be affected if A is made more stable without affecting the energy of the rest of the intermediates and product?

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