Textbook Question
Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.
e. trans-1-bromo-2-methylcyclohexane
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9. Alkenes and Alkynes
Dehydrohalogenation
Multiple Choice
Which of the following is the major organic product formed in the E2 dehydrohalogenation of (bromoethane) with a strong base such as ?
A
(sodium ethyl)
B
(bromoethane, starting material)
C
(ethanol)
D
(ethene)
Verified step by step guidance1
Identify the type of reaction: E2 dehydrohalogenation involves the elimination of a hydrogen atom and a halogen atom (in this case, bromine) from adjacent carbon atoms, resulting in the formation of a double bond (alkene).
Recognize the substrate: The starting material is bromoethane (\(\mathrm{CH_3CH_2Br}\)), which is a primary alkyl halide with bromine attached to the second carbon.
Consider the base: A strong base such as sodium hydroxide (\(\mathrm{NaOH}\)) will abstract a proton (H) from the carbon adjacent to the carbon bearing the bromine, facilitating elimination.
Determine the elimination site: Since bromoethane has only two carbons, the proton removed by the base must come from the carbon adjacent to the one bonded to bromine, leading to the formation of a double bond between the two carbons.
Write the product: The elimination results in the formation of ethene (\(\mathrm{CH_2=CH_2}\)), where the bromine and a hydrogen are removed, creating a carbon-carbon double bond.
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