Radical bromination of 2 methylbutane

  • Thread starter Thread starter xstetsonx
  • Start date Start date
  • Tags Tags
    Radical
Click For Summary
SUMMARY

The radical bromination of 2-methylbutane results in the formation of 1-bromo-3-methylbutane, 2-bromo-3-methylbutane, and 1-bromo-2-methylbutane due to the reactivity of primary carbons during the bromination process. The discussion clarifies that 3-bromo-3-methylbutane is incorrectly named and should be referred to as 2-methyl-2-methylbutane. The bromination occurs at the primary carbon furthest from the 2-methyl group, leading to a change in the naming convention based on bromine's higher priority over methyl in the IUPAC naming system.

PREREQUISITES
  • Understanding of radical bromination mechanisms
  • Familiarity with IUPAC naming conventions for organic compounds
  • Knowledge of the structure of 2-methylbutane
  • Basic principles of organic chemistry regarding substitution reactions
NEXT STEPS
  • Study radical bromination mechanisms in detail
  • Learn about IUPAC nomenclature for complex organic compounds
  • Explore the reactivity of primary versus secondary carbons in substitution reactions
  • Investigate the effects of substituents on the stability of radical intermediates
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in understanding radical reactions and nomenclature in organic chemistry.

xstetsonx
Messages
78
Reaction score
0
why would radical bromination of 2 methylbutane gives 1-bromo-3-methylbutane, 2-bromo-3-methylbutane, 3-bromo-3-methylbutane, and 1-bromo-2-methylbutane? i don't see any methyl shife in this reaction. Some one please help
 
Physics news on Phys.org
There is no such thing as 3-bromo-3-methyl butane. That's called 2-methyl-2-methyl butane instead.

Draw the structure of 2-methyl butane (it should have 5 carbons). Now brominate each of the primary carbons. When you brominate the primary carbon furthest from the 2-methyl substitution point you change the naming convention to reflect the position of the bromine instead of the methyl since bromine has a higher naming priority than methyl, ie. the 4-position in the starting material becomes the 1-position in the brominated product.
 

Similar threads

Replies
1
Views
2K
  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 1 ·
Replies
1
Views
3K
  • · Replies 2 ·
Replies
2
Views
2K
Replies
4
Views
5K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 4 ·
Replies
4
Views
92K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 3 ·
Replies
3
Views
2K