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Organic Chemistry

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Aromatic Compounds

Question
16 out of 16
 

The earliest predictions about the structure of benzene could not completely explain some of its properties. Later it was found that benzene has a cyclic structure which is commonly represented as follows:

image\27771 ch 18 passage 1.png

These two structures are resonance structures of benzene. Benzene is also commonly represented as shown below:

image\27782 ch 18 passage 1.png

A series of reactions were conducted using benzene and other aromatic compounds.

Reaction 1

In Reaction 1, benzene was reacted with n-propyl chloride in the presence of AlCl3.

Reaction 2

Nitrobenzene was reacted with nitric acid and sulfuric acid. The reaction occurred as follows:


image\Ch 18 pass react 2.png


All the following are false about Reaction 2, except that:

A Compound A is a meta product
B The major product is a 1,2 substituted product
C The major product is a para substituted product
D Compound C is a 1,3 substituted product
Ans. D To answer this question, we have to think about the substituent; the nitro group. The nitro group is a meta deactivating group. So the substitution predominantly results in a meta-product (1,3 substituted). According to the passage, compound C is the major product.

image\Solutions ch 18, Q 16.png

Aromatic Compounds Flashcard List

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