Carbocations, ions that contain a trivalent, positively charged carbon atom, react with water to give alcohols: How can you account for the fact that the following carbocation gives a mixture of two alcohols on reaction with water?
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Carbocations, which contain a trivalent, positively charged carbon atom, react with water to give alcohols as shown below. These reactions involve TWO steps. In the first step, a non-bonding electron pair on water forms a bond to the positively charged carbon of the carbocation. In the second step, a proton (H+) is released from the oxygen atom. Account for the fact that the carbocation shown in the second equation below gives the illustrated mixture of two alcohols on reaction with water. [Hint: Is the positive charge in the carbocation of the second equation constrained exclusively to reside on the carbon atom on which it is shown?]
Adi S.
Keeping in mind that carbocations have a trigonal planar structure, (a) write a structure for the carbocation intermediate and (b) write structures for the alcohol (or alcohols) that you would expect from reaction of iodocyclohexane in water: FIGURE CANT COPY
(a) Acetylide ion undergoes nucleophilic addition to aldehydes and ketones to give the species shown. Subsequent addition of water yields an acetylenic alcohol. Add curved arrows to the equations to show how the reaction occurs. (b) A nucleophilic site on a molecule can substitute for a halogen elsewhere in the same molecule to form a ring. Use curved arrows to show how the following cyclization is related to a conventional nucleophilic substitution.
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