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In radical chlorination of alkanes, non-equivalent hydrogens react with chlorine

ID: 1048898 • Letter: I

Question

In radical chlorination of alkanes, non-equivalent hydrogens react with chlorine atoms at different rates. At 35 degree C, primary, secondary, and tertiary C-H bonds react at relative rates of 1: 3.9: 5.2 respectively. These are conditions of kinetic control where product ratios are determined by relative rates of formation. For example, if A is formed twice as fast as B, the A: B product ratio will be 2. Consider chlorination of the alkane below at 35 degree C. Specify the most reactive C-H bond(s), a-c. Two non-equivalent C-H bonds of comparable reactivity should be separated by commas, i.e. a, c. Specify the site of chlorination in the major monochloro substitution product, a-c. Two products that form in comparable quantities should be separated by commas, i.e. a, c

Explanation / Answer

Q1.

the most reactiv eC-H bond is the one in B

since the carbon is most saturated, therefore, it ie most reactive for nucelophiles

This is pretty commonly studied in Markonikov Rules reaction

Q2.

the major choloro product is:

2-chloro-butane

smaller/minor products:

1-chloro-butane

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