Asked by Armstea Armstead on Sep 25, 2024
Verified
In the group shown below, which of the following alcohols is (are) likely to yield a product where skeletal rearrangement has occurred when treated with sulfuric acid?
3-methyl-3-pentanol, 3,3-dimethyl-2-butanol, 2,2-dimethylcyclohexanol
A) 3-methyl-3-pentanol only
B) 3,3-dimethyl-2-butanol only
C) 2,2-dimethylcyclohexanol only
D) both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol
E) None of these three alcohols is prone to rearrangement.
Skeletal Rearrangement
A type of chemical reaction or process where the carbon skeleton of a molecule is altered, leading to a structural rearrangement.
Sulfuric Acid
A highly corrosive strong mineral acid with the molecular formula H2SO4, widely used in industry and laboratory settings.
- Identify the products of alcohol dehydration reactions.
- Understand the influence of molecular structure on the reactivity and stability of organic compounds.
Verified Answer
GB
Garcia Baldwin1 day ago
Final Answer :
D
Explanation :
Both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol are likely to undergo skeletal rearrangement when treated with sulfuric acid. This is because they both have a tertiary carbocation intermediate that can undergo rearrangement to form a more stable carbocation. 3-methyl-3-pentanol does not have a tertiary carbocation intermediate and therefore is not prone to skeletal rearrangement.
Learning Objectives
- Identify the products of alcohol dehydration reactions.
- Understand the influence of molecular structure on the reactivity and stability of organic compounds.
Related questions
By What Mechanism Does Cyclohexanol React When Treated in Sulfuric ...
Which of the Following Compounds Is Least Reactive in the ...
When O-Fluorotoluene Is Treated with Sodium Amide, the Product Is ...
Which of the Following Amines Can Be Resolved into Enantiomers ...
An Ylide Is a Molecule That Can Be Described as ...