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Chapter 17: Q54P (page 907)

Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.

(a)

(b)

(c)

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Bromination

Bromination is a kind of electrophilic aromatic substitution reaction. A hydrogen atom is substituted by a bromine atom. The formation of Br+ ion is not favorable and thus presence of a Lewis acid like FeBr3 is necessary.

Since all electrophilic aromatic substitution occurs through the formation of carbocation intermediate, presence of electron donating group favors the reaction.

02

Major product formed from bromination of compound (a)

The major product formed after bromination of the given compound is shown below. The substitution takes place ortho to the methoxy group. The carbocation intermediate formed is stabilized by electron donation by the methoxy group.

03

Major product formed from bromination of compound (b)

The major product formed after bromination of the given compound is shown below. The substitution takes place ortho to the methyl group. The (+I) effect of the methyl group stabilizes the carbocation intermediate formed.

04

Major product formed from bromination of compound (c).

The major product formed after bromination of the given compound is shown below. The methoxy group is an electron donating group. The substitution takes place at the ortho position of the methoxy group.

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Most popular questions from this chapter

Propose a mechanism for the bromination of ethyl benzene shown above.

Indane can undergo free-radical chlorination at any of the alkyl positions on the aliphatic ring.

indane

  1. Draw the possible monochlorinated products from this reaction.
  2. Draw the possible dichlorinated products from this reaction.
  3. What instrumental technique would be most helpful for determining how many products are formed, and how many of those products are monochlorinated and how many are dichlorinated?
  4. Once the products have been separated, what instrumental technique would be most helpful for determining the structures of all the dichlorinated products?

Propose products (if any) and mechanisms for the following AICI3-catalyzed reactions:

猞� chlorocyclohexane with benzene

猞� methyl chloride with anisole

猞� 3-chloro-2,2-dimethylbutane with isopropylbenzene

What substituted alkene would you use in the Heck reaction to make the following products?

In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by a reaction with sodium chloroacetate, ClCH2CO2Na.

(a) Draw the structures of these compounds, and write equations for these reactions.

(b) One of the impurities in the Agent Orange used in Vietnam was 2,3,7,8-tetrachlorodibenzodioxin (2,3,7,8-TCDD), often incorrectly called 鈥渄ioxin.鈥� Propose a mechanism to show how 2,3,7,8-TCDD is formed in the synthesis of 2,4,5-T.

(c) Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis
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