Suggest a suitable sequence of reactions to prepare each of the following compounds from the indicated starting material. You can use any organic or inorganic reagent that you consider necessary.

a) 1-Bromobutane from 2-bromobutane

 

 

 

b) 1,2-Dibromopropane from 2-bromopropane

 

 

 

[1]  Elimination with strong base to form the alkene.

[2]  Anti halogenation of alkene with Br₂ /CCl₄

 

c) 1-Bromo-2-propanol from 2-propanol

 

 

 

[1] Dehydration of alcohol, to form the alkene.

[2] Formation of bromohydrin by reaction of alkene with Br₂ /H₂O

 

d) 1,2-Epoxypropane from 2-propanol

 

 

 

[1] Dehydration of alcohol, to form the alkene.

[2]  Alkene epoxidation with MCPBA

 

e) Cyclopentyl iodide from cyclopentane

 

 

[1]  Radical halogenation of the alkane. It cannot be done with I₂ /light.

[2]  Bimolecular nucleophilic substitution. Elimination followed by addition of HI to the alkene can also be performed.

 

f) trans-1,2-Dichlorocyclopentane from cyclopentane.