Arenes - Benzene - exam practice

benzene ring in phenol is more susceptible to nucleophilic attack

benzene ring in phenol is deactivated because the oxygen of the OH group is very electronegative

lone pair of electrons on the oxygen atom in phenol overlap with the delocalised electrons in the benzene ring

lone pair of electrons on the oxygen atom enable phenol to act as an electrophile

4-methylbenzene-1,3-diamine

4-methylbenzene-1,5-diamine

2-methylphenyldiamine

4-methylphenyldiamine

4

5

6

7

has significant covalent character

exists as a dimer in non-polar solvents

is an electron pair acceptor

is rapidly hydrolysed

N-H bonds are weaker than C-H bonds

nitrogen is very electronegative

the benzene ring has greater electron density in phenylamine than in benzene

phenylamine reacts by addition whereas benzene reacts by substitution

delocalised π-electrons

carbon-carbon bonds that are all the same length

lower thermodynamic stability than molecules of 1,3,5-cyclohexatriene

greater thermodynamic stability than molecules of 1,3,5-cyclohexatriene

acts as a solvent for the benzene and the nitric acid

protonates the benzene to speed up the reaction

protonates the nitric acid which acts as a base

reacts with the benzene to form a benzenesulfonic acid intermediate

lithium aluminium hydride in ether

concentrated ammonia in ethanol

potassium dichromate(VI) in sulfuric acid

tin in concentrated hydrochloric acid

benzene ring is stabilised

induced dipole-dipole forces between benzene molecules are stronger than the hydrogen bonds between ethanol molecules

hydrogen bonds between benzene molecules are stronger than the hydrogen bonds between ethanol molecules

C-H bonds in benzene are stronger than the C-H bonds in ethanol

benzene to produce an electrophile

benzene to produce a nucleophile

chloromethane to produce a nucleophile

chloromethane to produce an electrophile

CH₃CH₂OH

CH₃CHO

CH₃COCl

CH₃COOH

C₆H₅CH₂CH₂OH

C₆H₅CH₂CHO

C₆H₅COCH₃

C₆H₅CH(OH)CH₃

electrophilic addition

electrophilic substitution

nucleophilic addition

nucleophilic substitution

NO₂⁺

HNO₃

NH₄⁺

NO₂^-

$-150$

$-210$

$-360$

$-510$