Radicals

Question 1

do radical rxns do rearrangement?

Answer 1

no. never.

Question 2

do radicals get attacked from the front or the back?

Answer 2

both (similar to carboncation intermediates)

Question 3

what are the 2 main types of radical rxns you need to know for class?

Answer 3

radical halogenation (halogens and single bonds) and radical bromation (involving double bonds)

Question 4

where does the hydrogen get attacked when an alkane experiences a radical halogenation?

Answer 4

internal carbon if the halogen is Br

terminal carbon AND internal carbon if the halogen is Cl

Question 5

what happens in a radical halogenation rxn?

Answer 5

H is attacked (from internal carbon, terminal carbon, or both, depending on the halogen) and the halogen takes the hydrogen’s place.

Question 6

do radical halogenation rxns involve single bonds or double bonds?

Answer 6

single

Question 7

which radicals are the most stable for radical rxns: tertiary, secondary, or primary?

Answer 7

tertiary

Question 8

which radicals do radical bromination rxns favor: tertiary, secondary, or primary?

Answer 8

tertiary/most stable

Question 9

what reagent do you need to facilitate an (radical) allylic bromination rxn?

Answer 9

NBS

Question 10

what’s the difference between a radical halogenation with bromine and a radical allylic bromination?

Answer 10

halogenation involves single bond where Br replaces a hydrogen

bromination involves a double bond where Br replaces a hydrogen in an allylic position

Question 11

what/where is the allylic position on an electrophile?

Answer 11

the carbons directly next to/attached the carbons in a double bond

Question 12

what type of rxn is the radical allylic bromination rxn: addition, substitution, elimination?

Answer 12

substitution

Question 13

why is resonance important to radical allylic bromination products?

Answer 13

they give you different products