Orgo question
Started by Ferdowsi
bromine free radicals reacts slow thats why they attack the 3ary carbon. but cl free radicals react very very fast and attacks primary carbon.
Everything always prefers tertiary, BUT this is a complicated question.
I pulled out the big Princeton book.
Here are the numbers: TERTIARY SECONDARY PRIMARY
BROMINATION 1640 82 1
CHLORINATION 5.3 3.9 1
But it also depends on how many hydrogens are available.
If there was 1 tertiary and 1 secondary hydrogen then the the Chlorine will bond to the tertiary one because as you can see it is more favorable (5.3>3.9). But if there were two secondaries hydrogens and 1 tertiary then it would add secondary (2 x 3.9>5.3)
For bromines, ALWAYS TERTIARY, unless you have a 20 to 1 ratio of tertiaries to secondaries.
Chlorine is more desperate to add than Bromine. Chlorine reacts faster.
Hope this helps, took a while to write....
Stability favors the radical on the tertiary carbon however chlorine is more reactive due to its higher electronegativity and electron affinity thus it discriminates less.
