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Organic Chemistry - Chlorination of Propane

The chlorination of propane yields 4 different dichloropropanes of formula C3H6Cl2. Using the following information to identify dichloropropanes A,B,C,D.
i. If each dichloropropane is further chlorinated to yield trichloropropanes. Compound A gave one trichloropropane, B gave two, C and D each gave three.
ii. Dichloropropane D has a chiral carbon.

Solution Preview

If you sit down to draw out the four possible dichloropropanes, you will find out that they are:

1,1-dichloropropane
1,2-dichloropropane
2,2-dichloropropane
1,3-dichloropropane

The only one with a chiral carbon is 1,2-dichloropropane. Its structure is:

CH2Cl-CHCl-CH3
*

The chiral ...

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Organic Chemistry - Chlorination of Propane

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