P-tert.-Butyltoluene

The reaction of N bromosuccimmide with the following com pounds has been reported in the chemical literature Each compound yields a single product in 95% yield Identify the product formed from each starting material (a) p-tert Butyltoluene (b) 4 Methyl 3 nitroanisole... 

When two positions are comparably activated by alkyl groups substitution usually occurs at the less hindered site Nitration of p tert butyltoluene takes place at positions ortho to the methyl group m preference to those ortho to the larger tert butyl group This IS an example of a stenc effect... 

Butyl ether Butyl carbitol /i-Butyl glycidyl ether Butyl mercaptan p-tert-Butyltoluene Carbon disulphide Carbon dioxide Carbon monoxide Carbon tetrachloride Carbonyl sulphide Carbary ... 

Butyl cellosolve (2-butoxy ethanol) n-Butyl glycidyl ether n-Butyl mercaptan n-Butylamine p-tert-Butyltoluene... 

Butyl cellosolve, see 2-Butoxyethanol tert-Butyl chromate (as CrOj) n-Butyl glycidyl ether n-Butyl lactate Butyl mercaptan p-tert-Butyltoluene Cadmium, dust and salts (as Cd) Cadmium, fume (as Cd)... 

SAMPLE SOLUTION (a) The only benzylic hydrogens in p-tert-butyltoluene are those of the methyl group that is attached directly to the ring. Substitution occurs there to give p-tert-butylbenzyl bromide. 

Toluene p-tert-Butyltoluene 4-rert-Butyl- 2-nitrotoluene... 

Zollinger D, Griesbach U, Putter H, Comninellis C (2004) Methoxylation of p-tert-butyltoluene on boron-doped diamond electrodes. Electrochem Commun 6 600-604... 

---