Question

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

Short answer

In the presence of dimethyl sulphide, 2,3-dimethyl-2-hexene reacts with ozone at low temperatures to produce two equivalent ketones.

When 2,3-dimethyl-2-hexene is ozonated and then treated with dimethyl sulphide, the result is pentan-2-one and propan-2-one.

Step-by-step solution

a) 

In the presence of dimethyl sulphide, 2,3-dimethyl-2-hexene reacts with ozone at low temperatures to produce two equivalent ketones.

When 2,3-dimethyl-2-hexene is ozonated and then treated with dimethyl sulphide, the result is pentan-2-one and propan-2-one.

b)

In the presence of dimethyl sulphide, methylenecyclopentane reacts with ozone at low temperatures to produce two equivalent ketones.

Whenmethylenecyclopentaneis ozonated and then treated with dimethyl sulphide, the result is cyclopentanone and formaldehyde.

c)

In the presence of dimethyl sulphide, cyclohexa-1,4-diene reacts with ozone at low temperatures to produce one equivalent ketone.

When cyclohexa-1,4-diene is ozonated and then treated with dimethyl sulphide, the result is malonaldehyde.

d)

In the presence of dimethyl sulphide, 2-methylcyclohexa-1,3-diene reacts with ozone at low temperatures to produce two equivalent ketones.

When 2-methylcyclohexa-1,3-diene is ozonated and then treated with dimethyl sulphide, the result is succinaldehyde and oxalaldehyde

e)

In the presence of dimethyl sulphide, 1-methylcyclohexa-1,3-diene reacts with ozone at low temperatures to produce two equivalent ketones.

When1-methylcyclohexa-1,3-diene is ozonated and then treated with dimethyl sulphide, the result is 3-oxobutanal and oxalaldehyde.

f)

In the presence of dimethyl sulphide, 4-methylenecyclohex-1-ene reacts with ozone at low temperatures to produce two equivalent ketones.

When,4-methylenecyclohex-1-ene is ozonated and then treated with dimethyl sulphide, the result is3-oxohexanedial and formaldehyde.