Experimental Organic Chemistry: A Miniscale and Microscale Approach

Section 21.3 SYNTHESIS OF 1-BROMO-3-CHLORO-5-IODOBENZENE. Part E. PREPARATION OF

4-BROMO-2-CHLORO-6-IODOANILINE

NAME (print): DATE:

INSTRUCTOR: LABORATORY SECTION:

1. Mechanistically, the reaction to be performed (underline all answers that apply) is (a) an elimination reaction,
(b) a nucleophilic substitution reaction, (c) a nucleophilic addition-elimination reaction, (d) an electrophilic
substitution reaction, (e) a free-radical substitution reaction, (f) an oxidation of the aromatic substrate, (g) a
reduction of the aromatic substrate, (h) none of these.

2. What is the limiting reagent in this reaction? Show your work.

3. Why does iodination rather than chlorination occur when 4-bromo-2-chloroaniline is treated with iodine
monochloride?

4. Why is the iodination being performed on 4-bromo-2-chloroaniline rather than 4-bromo-2-chloroacetanilide?

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 Experimental Organic Chemistry: A Miniscale and Microscale Approach

5. List the possible effects of inhaling excessive amounts of iodine monochloride.

6. The melting point of iodine monochloride is ; its boiling point is .

7. Underline the media appropriate for extinguishing fires involving sodium iodine monochloride: Water
Carbon dioxide Chemical powder Foam

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©2006 Thomson Brooks/Cole