Chemistry · Hydrocarbons
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Which of following functional groups are deactivating and not ortho, para directing?
- A
–R
- B
–COR
- C
–NH2
- D
NR2
Ortho and para directing grps release electrons to the benzene ring increasing the chemical reactivity of the benzene ring towards electrophiles. Meanwhile meta directing grps withdraw the electrons from the benzene ring towards themselves decreasing their availability towards electrophiles. Therefore the answer will be B.
a) –R:
The functional group –R represents an alkyl group, which is a hydrocarbon chain. Alkyl groups are generally weakly deactivating and not ortho, para directing in electrophilic aromatic substitution reactions. Alkyl groups have a slightly electron-donating effect due to the release of electron density through hyperconjugation. However, their effect is not strong enough to significantly activate the benzene ring toward electrophilic substitution, and they do not direct incoming substituents to the ortho and para positions.
b) –COR:
The functional group –COR represents a carbonyl group attached to an alkyl or aryl group. Carbonyl groups are strongly deactivating and meta directing in electrophilic aromatic substitution reactions. The presence of the electron-withdrawing carbonyl group withdraws electron density from the benzene ring, making it less reactive toward electrophiles. Additionally, the carbonyl group directs incoming substituents to the meta position relative to itself.
c) –NH2:
The functional group –NH2 represents an amino group, which is weakly activating and ortho, para directing in electrophilic aromatic substitution reactions. The amino group has a lone pair of electrons that can donate electron density to the benzene ring through resonance, making the ring more reactive toward electrophiles. Moreover, the amino group directs incoming substituents to the ortho and para positions.
d) –NR2:
The functional group –NR2 represents a secondary amine group, where R can be an alkyl or aryl group. Secondary amine groups are weakly activating and ortho, para directing in electrophilic aromatic substitution reactions. Similar to the –NH2 group, the lone pair of electrons on the nitrogen atom can donate electron density to the benzene ring through resonance, making it more reactive toward electrophiles. Also, the –NR2 group directs incoming substituents to the ortho and para positions.
Tagged under Chemistry · Hydrocarbons · 2013