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Synthesis of aromatics

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1. On the basis of electronic theory, explain the following observations:

a. The -N(CH3)2 group is an ortho, para director, and strongly activates the ring, whereas the -N(CH3)3 group is a meta director and deactivates the ring toward electrophilic substitution.
b. The -NO2 group is a meta director, and its presence on the ring makes electrophilic substitution more difficult as compared with the -NH2 group, which is an ortho, para director.

2. Devise a suitable reaction sequence in which each of the following compounds can be prepared from benzene in good yield. Assume ortho and para isomers are separate from one another, and use any other reagents you desire.
a. p-Bromoisopropylbenzene
b. m-Nitrobenzenesulfonic acid
c. p-Tert-butylbenzenesulfonic acid
d. m-Xylene

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Solution Preview

The N(CH3)2 group is an electron donating group. Hence the aromatic ring becomes more electron rich and a better nucleophile. On the other hand the +N(CH3)3 is an electron withdrawing ...

Solution Summary

The directing effects of substituent groups are explained. A few aromatic compounds are also prepared.

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Aromatic Imide Formation: Synthesis of N-Phenylmaleimide

1. The second step in the reaction to from the imide is much slower than that of the first stage (formation of the acid amide). Explain.

2) Phthalimide has a Ka = 5 x 10^-9. Write an equation for the reaction of phthalimide with potassium amide (a strong base) in N,N dimethylformamide (DMF) solvent. Name the product. See attachment 1 for more information.

3) Predict Which of the following species is most acidic? Phthalimide (see attachment 1) or Benzamide (see Attachment 2)? Explain.

4) The phthalimide anion is a strong nucleophile. It can react easiest with primary alkyl halides to form substituted phthalimides.

Phthalimide (see attachment #1), K+(this is next to a N- in Phthalimide) +Ch3CH2BR ---> Phthalimide (The N is attached to CH2CH3) + KBr.

Suggest a suitable mechanism for this reaction.

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