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Magazine Chapter 17: Q32P (page 888)
Predict the major products of the following reactions.
(a) toluene + excess CI2 (heat, pressure)
(b) benzamide ( PhCONH2 ) + Na (liquid NH3, CH3 CH2OH)
(c) o-xylene + H2 (1000 psi, 100 掳C, Rh catalyst)
(d) p-xylene + Na (liquid NH3, CH3CH2OH )
(e) 
Short Answer
(a)
(b)
(c)
(d)
(e)
Step by step solution
Chlorination, Catalytic hydrogenation and Birch reduction.
When benzene reacts with an excess of chlorine under heat and pressure light), six chlorine atoms add to form 1,2,3,4,5,6-hexachlorocyclohexane.
Catalytic hydrogenation of benzene to cyclohexane takes place at elevated temperatures and pressures, often catalyzed by ruthenium or rhodium-based catalysts. Substituted benzenes react to give substituted cyclohexanes; disubstituted benzenes usually give mixtures of cis and trans isomers.
A reaction in which benzene derivatives are reduced to non-conjugated cyclohexa-1,4-dienes by treatment with sodium or lithium in a mixture of liquid ammonia and alcohol is called the birch reduction.
Subpart (a) The major products of the reaction of toluene with excess of chlorine (heat, pressure).
Subpart (b) The major products of the reaction of benzamide ( PhCONH2 ) + Na (liquid NH3,CH3CH2OH ).
Subpart (c) The major products of the reaction of o-xylene + H2 (1000 psi, 100 °C, Rh catalyst).
Subpart (d) The major products of the reaction of p-xylene + Na (liquid NH3, CH3CH2OH).
Subpart (e) The major products of the reaction of
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