CHEM1002 Reactivity and Function in Chemistry

MODULE C: Self-study worksheet

This worksheet covers assessment like questions in Modules A and D.

1. Consider the following reaction.

O
O AlCl3
+ CH3
Cl CH3

(a) What is the electrophile in the reaction?

(b) How is the electrophile formed? Draw a mechanism.

(c) Using curly arrows, draw a mechanism for the formation of the product.
2. Complete the following scheme.

H NaI
Cl SN2 Substitution
+ NaCl
H3C

(include stereochemistry)

(a) What is the nucleophile in the reaction?

(b) What is the leaving group in the reaction?

(c) What is the R/S configuration of the product?

3. Complete the following scheme.

H H2O
Cl SN1 Substitution
H3C

(intermediate) (an alcohol)

4. Identify the E/Z nomenclature of these compounds.

Li
Br CH3
CO2H
CH3

5. What is the product(s) of the following reactions (include stereochemistry when

required).

(a)
O
NaOH
OH

(b)
O
2 x NaOH
Cl

(c)
O H2SO4 (Cat.)

OH CH3OH

(d)
O
NH(CH3)2 (2 Eq.)
Cl
(e)
O CH3MgI
Then H3O+

(f)
O
NH(CH3)2 (2 Eq.)
Cl

(g) Note: An imine behaves in the same way as a ketone.

CH3MgCl
The H3O+
N

(h) Draw the product in the most stable chair conformation.

Br2, CH3CH2OH (solvent)

7. Using a flow diagram how would you separate a mixture of the following
components using acid base chemistry.

O H3C CH3

OH OH

Cl Cl
8. Consider the reaction shown below.

H
HBr
H
H

(a) What is the electrophile in this reaction?

(b) What role does bromide play in this reaction?

(c) Two products are possible in this reaction draw both of them and identify the
major product.

(d) Draw a full mechanism for the formation of both products using curly arrows and
draw any intermediates in the reaction.

(e) Based on your mechanism in part (d) explain why the major product is formed.