Chapter 8: Problem 52
Compound \(\mathrm{A}\left(\mathrm{C}_{7} \mathrm{H}_{15} \mathrm{Br}\right)\) is not a primary alkyl bromide. It yields a single alkene (compound B) on being heated with sodium ethoxide in ethanol. Hydrogenation of compound B yields 2,4 -dimethylpentane. Identify compounds \(\mathrm{A}\) and \(\mathrm{B}\).
Short Answer
Step by step solution
Understand the Structure of Compound A
Analyze the Elimination Reaction
Deduce the Structure of Compound B
Assign Structure to Compound A
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Elimination Reactions
A common method for these reactions involves using a strong base such as sodium ethoxide in ethanol. This base encourages the elimination of a hydrogen atom and a leaving group, which in this exercise is a bromine atom. The result is the formation of an alkene — a molecule with a carbon-carbon double bond. Elimination reactions are often regioselective, leading to a preferred formation of the more stable alkene, as seen in our reaction where a single alkene, compound \(B\) , is produced.
- Type: Typically E2 mechanism for secondary and tertiary alkyl halides.
- Requirements: Strong base and usually heat.
- Result: Formation of an alkene.
Alkyl Bromide
The alkyl bromide in this exercise is not primary but secondary or tertiary, which means the carbon bonded to the bromine is attached to two or three other carbons, respectively. This branching facilitates elimination reactions, leading to fewer resultant alkenes. The nature of the branching and the position of the bromine determine the type of alkene formed after the elimination. Such positioning is crucial for predicting the structure of the resulting alkene. For example, the alkyl bromide in our problem, designated as compound \(A\) , undergoes elimination to form a single unique alkene, compound \(B\) .
Hydrogenation
During hydrogenation, the double bond in the alkene is broken, and a hydrogen atom is added to each of the carbon atoms that were initially bonded by the double bond. This process effectively saturates the molecule, turning the previously unsaturated compound \(B\) into a saturated alkane, enabling us to deduce its original structure before hydrogenation. It is through understanding hydrogenation that one can predict the geometry and connectivity of the precursor alkene.
Structural Isomerism
A secondary or tertiary alkyl bromide can be rearranged spatially to give different compounds with unique reactivity and properties. These varied structures can lead to different alkenes upon an elimination reaction. Structural isomerism explains why only a single alkene, compound \(B\) , is formed from \(A\), due to its specific arrangement.
- Type: Chain or positional isomerism in the alkyl bromide.
- Effect: Formation of a specific alkene upon elimination.
- Importance: Helps in predicting the outcomes of chemical reactions.