Asked by karleigh rivas on May 31, 2024
Verified
Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?
A) water + dilute acid
B) water + concentrated acid
C) oxymercuration-demercuration
D) hydroboration-oxidation
E) none of the above
Markovnikov Addition
A rule in organic chemistry that describes the outcome of addition reactions, specifically that hydrogen is added to the carbon with the greatest number of hydrogens in an unsaturated hydrocarbon.
Skeletal Rearrangement
A type of organic reaction where the carbon skeleton of a molecule is rearranged to give a structurally different molecule.
- Forecast the results of chemical reactions concerning alkenes.
Verified Answer
TC
Titans ChickJun 07, 2024
Final Answer :
C
Explanation :
Oxymercuration-demercuration is the best reaction sequence to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement. It adds a mercuric acetate (Hg(OAc)2) and water to the double bond, forming a mercurinium ion intermediate that reacts with water to form an alcohol. The demercuration step removes the mercury atom and regenerates the alkene. This reaction sequence avoids rearrangements and produces a Markovnikov product.
Learning Objectives
- Forecast the results of chemical reactions concerning alkenes.
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