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NCERT Class XI Chemistry Organic Chemistry Some basic principles and Techniques Solutions

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Question : 11 of 40
Marks: +1, -0
Draw the resonance structures for the following compounds. Show the electron shift using curved-arrow notation.
(a) C6H5OH\mathrm{C_6H_5OH}
(b) C6H5NO2\mathrm{C_6H_5NO_2}
(c) CH3CH=CHCHO\mathrm{CH_3CH=CHCHO}
(d) C6H5–CHO\mathrm{C_6H_5–CHO}
(e) C6H5−C+H2\mathrm{C_6H_5-C^{+}H_2}
(f) CH3CH=CHC+H2\mathrm{CH_3CH=CHC^{+}H_2}
Solution:  
(a) Resonance structures of phenol are
Phenol is a planar molecule. The p-orbitals on each carbon atom lie perpendicular to the plane of the molecule, the oxygen atom lying in its p-orbital is also perpendicular to the molecule. Consequently the p-orbital overlap, between O and C takes place and the resonance structures arise.
(b) –NO2\mathrm{–NO_2} is an electron withdrawing group. As a result, it polarises the benzene molecule and resonance occurs as shown :
(c) CH3CH=CHCHO\mathrm{CH_3CH=CHCHO} is an α,β-unsaturated aldehyde where the C = C gets polarised due to the neighbouring electron withdrawing – CHO group.
(d) Oxygen being highly electronegative pulls the π-electron cloud of the C=O towards itself thereby leaving the carbonyl carbon with a positive charge. In order to compensate this electron deficiency, the electron cloud from the ring moves towards it and the resonance structures arise.
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