Benzene problems

Formulate the following derivatives of benzene:

1) 1-Ethyl-3-methylbenzene
2) p-Dimethylbenzene
3) 1-Butyl-3-ethylbenzene
4) o-Chloronitrobenzene
5) m-Bromochlorobenzene
6) p-Diisopropylbenzene
7) 1-tert-Butyl-4-methylbenzene
8) o-Allylvinylbenzene
9) m-Ethylpropylbenzene
10) 2-Ethyl-1,4-dimethylbenzene
11) 4,5-Diphenyl-1-octene
12) 2-phenyl-4-methylhexene
13) 1-(methylethyl)-2-(2-methylpropyl)benzene
14) 6-Phenyl-3-methylhexa-1,4-diene
15) cis-1-phenyl-1-butene
16) trans-2-phenyl-2-butene
17) 7-Ethyl-4,5-diphenyldec-5-en-1-yne
18) m-Dicyclohexylbenzene
19) p-Cyclobutylcyclobutylbenzene
20) 3-(1,1-Diphenylethyl)-3-methylhex-1-en-5-yne.

Starting from benzene or toluene, develop the synthesis of the following compounds:


The rates of nucleophilic substitution of nitrohalogenobenzenes depend on the halogen displaced. The order F>> Cl> Br> I, is the opposite of that observed for fitness as a leaving group in most other substitution reactions. How is this information consistent with the two-step mechanism for nucleophilic aromatic substitution?

Arrange the following compounds in increasing order of nucleophilic aromatic substitution reaction rate:

Chlorpromazine is a drug used for the treatment of certain mental disorders (schizophrenia, acute psychosis, delusions, etc.). Its synthesis can be carried out according to the following scheme. Complete it and indicate what type of reaction occurs in each case.

Roberts et al. carried out an important experiment to prove the existence of benzine. Chlorobenzene labeled with 14C at the position to which the chlorine was attached was treated with sodium amide in liquid ammonia and the aniline formed was analyzed for the 14C position. The results are indicated in the figure. Show how these data are consistent with the benzyne intermediate.