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
c) 1-Bromo-2-propanol from 2-propanol
d) 1,2-Epoxypropane from 2-propanol
e) Cyclopentyl iodide from cyclopentane
f) trans-1,2-Dichlorocyclopentane from cyclopentane.
 
 
SOLUTION:
 
a) 1-Bromobutane from 2-bromobutane
 
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b) 1,2-Dibromopropane from 2-bromopropane
 
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[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
 
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[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
 
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[1] Dehydration of alcohol, to form the alkene.
[2]  Alkene epoxidation with MCPBA
 
e) Cyclopentyl iodide from cyclopentane
 
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[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.
 
problemas-reacciones-alquenos