Reactive Intermediates

Question 1

Peroxides have weak bonds due to lone pair repulsion. Draw the mechanism of a peroxide radical generation

Answer 1

Question 2

Azo compounds can also be used for radical generation such as AIBN, draw a mechanism for radical generation

Answer 2

Question 3

Explain the capdodative effect

Answer 3

Both EWG and EDG groups stabilise radicals, this is due to overall stabilisation on molecular orbital formation

SOMO interacts with EWG pi* orbital and EDG lone pair orbital

Question 4

How is tributyltinhydride used for radical reaction

Answer 4

Can make Bu₃Sn^. radical

Soft tin abstracts iodine or bromine allowing for radical reaction to happen

Its worth noting that termination with H. can take place immediately after the abstraction occurs as a side product

Question 5

How can alpha elimination occur to form carbenes?

Answer 5

Question 6

How can diazo compounds be used to form carbenes?

Answer 6

Question 7

Exlpain the difference between a singlet and a triplet state radical

Answer 7

Has to do with the coupling of electrons. Paired is a singler and unpaired is a triplet

Will effect reactivity by being two “radicals” or a lone pair and an empty orbital

Question 8

Draw a hoffman rearrangment to form amines from amides

Answer 8

Question 9

How do you form nitrenes using alpha elimination

Answer 9

Question 10

How to form nitrenes from azides?

Answer 10

Question 11

How to form an aryne from elimination

Answer 11