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Chapter 8-4 - Addition of Water: Hydration of Alkenes
Organic Chemistry 307: Chapter 8 - Reactions of Alkenes; Section 4 - Addition of Water: Hydration of Alkenes
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Organic Chemistry
Undergraduate 3
11/17/2011

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Term
A __________ is a reaction in which an alkene reacts with water in the presence of a strongly acidic catalyst to form an __________.
Definition
1) Hydration
2) Alcohol
Term
A hydration reaction is when an alkene reacts with __________ in the presence of a strongly __________ catalyst to form an alcohol.
Definition
1) Water
2) Acidic
Term
A hydration reaction features a __________ atom adding to one carbon and a __________ group adding to another.
Definition
1) Hydrogen
2) Hydroxyl
Term
Hydration of an alkene is the reverse of the __________ of alcohols.
Definition
1) Dehydration
Term
For dehydrating alcohols, a concentrated dehydrating __________ (such as __________ or __________) is used to drive the equilibrium to favor the __________.
Hydration of an alkene, on the other hand, is accomplished by adding excess __________ to drive the equilibrium toward the __________.
Definition
1) Acid
2) H2SO4 or H3PO4
3) Alkene
4) Water
5) Alcohol
Term
The __________ __________ __________ __________ states that a forward reaction and a reverse reaction taking place under the same conditions (as in an equilibrium) must follow the same reaction pathway in microscopic detail.
Definition
1) Principle of microscopic reversibility
Term
According to the __________ __________ ____________________, we can write the hydration mechanism of an alkene by reversing the order of the steps of the __________: protonation of the double bond forms a __________. Nucleophilic attack by water followed by loss of a proton gives the __________.
Definition
1) Principle of microscopic reversibility
2) Dehydration
3) Carbocation
4) Alcohol
Term
*Mechanism 8-4: Acid-Catalyzed Hydration of an Alkene*
Step 1: Protonation of the double bond forms a __________.
Step 2: Nucleophilic attack by __________ gives a protonated alcohol.
Step 3: Deprotonation gives the __________.
Definition
1) Carbocation
2) Water
3) Alcohol
Term
Orientation of Hydration:
Step 1 of the hydration mechanism is similar to the first step in the addition of HBr: the proton adds to the (less/more) substituted end of the double bond to form the (less/more) substituted carbocation.
__________ attacks the carbocation to give (after loss of a proton) the __________ with the hydroxyl group on the (less/more) substituted carbon.
Definition
1) Less
2) More
3) Water
4) Alcohol
5) More
Term
Similar to the addition of hydrogen halides, hydration is __________: it follows __________ __________, giving a product in which the new hydrogen has added to the (less/more) substituted end of the double bond.
Definition
1) Regioselective
2) Markovnikov's rule
3) Less
Term
Reactions that follow Markovnikov's rule will generally feature a __________ adding to the (less/more) substituted end of a double bond, with the remaining functional group attaching to the (less/more) substituted end.
Definition
1) Proton
2) Less
3) More
Term
Like other reactions that involve carbocation intermediates, hydration may take place with __________.
Definition
1) Rearrangement
Term
Any reaction that features a carbocation can generally undergo __________.
Definition
1) Rearrangement
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