Master Organic Chemistry Reaction Guide

Addition of aqueous acid to alkenes to give alcohols

Description: Addition of aqueous acid to alkenes leads to the formation of alcohols.

This page is available to MOC Members only.
Sign up here for about 30 cents/ day!






Comment section

20 thoughts on “Addition of aqueous acid to alkenes to give alcohols

  1. For the last rearrangement with the shift, when does this shift take place? At what step of the mechanism?

  2. Hi James,

    With the example with the alkene with the pentane, how come the OH attached to the carbon that’s part of the pentane instead of the next carbon to the right that’s part of the side chain? Isn’t the OH suppose to attach to the more substituted carbon that’s part of the double bond??

    Thank you

    1. Hi Casey! last example is a rearrangement. Forms a secondary carbocation initially and then there is a hydride shift which generates a (more stable) tertiary carbocation which is then trapped by water.

  3. With problems where you’re given the reactant and the product and you’re to guess the reagent how do you know whether to choose aqueous acid or oxymercuration?

    1. Oxymercuration is generally the best and safest choice. Aqueous acid leads to carbocation formation, and carbocations can rearrange under certain conditions.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.