E* LE E* C2 -СЗ `N' 'N' pyridine pyrrole

Introductory Chemistry: A Foundation
9th Edition
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Donald J. DeCoste
Chapter20: Organic Chemistry
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Problem 4ALQ: How many different possible “tetramethylbenzenes” exist? Provide structural formulas and names for...
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Question

Explain the reactivity and orientation effects observed in each heterocycle.
a. Pyridine is less reactive than benzene in electrophilic aromatic
substitution and yields 3-substituted products.
b. Pyrrole is more reactive than benzene in electrophilic aromatic
substitution and yields 2-substituted products.

E*
LE
E*
C2
-СЗ
`N'
'N'
pyridine
pyrrole
Transcribed Image Text:E* LE E* C2 -СЗ `N' 'N' pyridine pyrrole
Expert Solution
Step 1

Aromatic compounds generally shows electrophilic substitution reactions. In electrophilic substitution reactions electrophile attack on benzene ring because benzene ring is electron rich due to presence of pi bonds.

 

 

 

Step 2

a) Pyridine is less reactive than benzene in electrophilic aromatic substitution reaction due to the presence of more electronegative atom nitrogen than carbon atom.

Nitrogen atom pull electrons towards it self and at position 3 in the pyridine the electron density is much higher as compared to position 2 and 4.Therefore, electrophile attack easily on the position 3.

Chemistry homework question answer, step 2, image 1

 

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