I performed an experiment doing free radical chlorination of 1-chlorobutane + AB

Question

I performed an experiment doing free radical chlorination of 1-chlorobutane + ABCN + SO2Cl2.

Resulted in four dichloro compunds. Please see question and picture:         

Four peaks representing the constitutional isomers of the reaction products from this experiment

will be found by GC analysis (See Picture).

QUESTION: How many total isomers (constitutional isomers plus steroisomers) are actually produced in this reaction?

List and identify them by chemical formula.

GLC analysis of mixture from chlorination of 1-chlorobutane (numbers in parentheses are boiling points at 760 torr and peak areas, respectively). Peak 1: solvent; peak 2:1-chlorobutane (77-78 degree C, 2719); peak 3; 1,1-dichlorobutane (114-115 X, 487); peak 4:1,2-dichlorobutane (121-123 degree C, 1771); peak 5:1,3-dichlorobutane (131-133 degree C, 3367); peak 6; 1,4-dichlorobutane (161-163 degree C, 1137); column and conditions: 0.5-mm times 30-m, 0.25-v film of SE-54; 80 degree C, 40 mL/min.

Explanation / Answer

There are total 6 isomers (constitutional isomers plus steroisomers) that are actually produced in the reaction.

There are 4 structural isomers formed

CH(Cl)2 - CH2 - CH2 - CH3 (1,1-dichlorobutane)

CH2Cl - CHCl - CH2 - CH3 (1,2-dichlorobutane)

CH2Cl - CH2 - CHCl - CH3 (1,3-dichlorobutane)

CH2Cl - CH2 - CH2 - CH2Cl (1,4-dichlorobutane)

The darken one have one chiral carbon so they have stereoisomers

*

CH2Cl - CHCl - CH2 - CH3 (1,2-dichlorobutane) (total 2 R and S)

*
CH2Cl - CH2 - CHCl - CH3 (1,3-dichlorobutane) (total 2 R and S)

The carbon marked with star are chiral in the above two so both have two stereoisomers with R and S configuration.

Hence we get a total of = 1+ 2 +2 +1 = 6 Isomers of all kind

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