Ch. 10 - Addition ReactionsSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Acid-Catalyzed Hydration

See all sections
Sections
Addition Reaction
Markovnikov
Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration
Hydroboration
Hydrogenation
Halogenation
Halohydrin
Carbene
Epoxidation
Epoxide Reactions
Dihydroxylation
Ozonolysis
Oxidative Cleavage
Alkyne Oxidative Cleavage
Alkyne Hydrohalogenation
Alkyne Halogenation
Alkyne Hydration
Alkyne Hydroboration
Additional Practice
Thermodynamics of Addition-Elimination Equilibria
Stereospecificity vs. Stereoselectivity
Sulfonation
Oxymercuration-Reduction Full Mechanism
Hydroboration-Oxidation Full Mechanism
Alkoxymercuation
Interhalogenation
Haloether Formation
Simmons-Smith Addition Mechanism
Regiospecificity of Acid-Catalyzed Ring Openings
Anti Vicinal Dihydroxylation
Ozonolysis Full Mechanism
Ozonolysis Retrosynthesis
LiBr and Acetic Acid for Anti Vinyl Dihaldes
Addition Reagent Facts
Predicting Stereoisomers of Addition Reactions
Addition Missing Reagent
Addition Synthesis
Addition Texas Two-Step
Addition Retrosynthesis
Addition to Concave vs. Convex Rings

This is the first of three ways to add alcohol to a double bond. It is similar to hydrohalogenation in terms of mechanism, however it will require a protonation and deprotonation step since it is acid-catalyzed. 

Concept #1: General properties of acid-catalyzed hydration.    

This reaction uses the same reagents as acid-catalyzed dehydration, so how do you know which reaction to use? Just look at what you are starting with:

General Reaction:

Note: The squiggly line on the product just means “indeterminate stereochemistry”. We aren’t sure where that –H will add, so we’ll just draw it on a squiggly line. 

Example #1: A worked-example of the acid-catalyzed hydration mechanism.     

Practice: Predict the product of the following reaction.

Additional Problems
How many atoms and electrons are directly involved in the bond-making and bond-breaking of the reaction given below?  Choose the right answer.  The first step of hydronium ion-catalyzed addition of water to an alkene a) four atoms, four electrons b) four atoms, three electrons c) four atoms, two electrons d) three atoms, four electrons e) three atoms, three electrons f) three atoms, two electrons  g) two atoms, three electrons h) two atoms, two electrons
Predict the product(s) or reagents of the following reactions.
Specify reagents suitable for converting 3-ethyl-2-pentene to each of the following: (d) 3-Ethyl-3-pentanol 
Specify reagents suitable for converting 3-ethyl-2-pentene to each of the following: (e) 3-Ethyl-2-pentanol 
The acid catalyzed addition of water to alkenes is a common method to prepare alcohols. For the example below, show the mechanism of this reaction. Include all flows of electrons, charges and intermediates. The mechanism MUST show how the acid is catalytic. 
Provide a detailed mechanism for the following reaction using a curved arrow notation.
(c) Write equations describing the preparation of the tertiary alcohol of molecular formula C5H12O by acid-catalyzed hydration of two different alkenes. 
Fill in the box with the product of the following reaction of alkenes. Draw only the PREDOMINATE REGIOISOMER and indicate stereochemistry by drawing dashes and wedges where appropriate. When a racemic mixture is formed you must draw both enantiomers and write RACEMIC in the box. 
Draw the starting material that under the given reaction conditions, result in the following product.
Follows Markovnikov’s Rule a)  Hydrogen goes to the double bonded carbon with _______ hydrogens. ( ______ substituted alkene carbon)  b)    Hydroxide ion goes to the ___________ stable carbocation  
The following problems are a new format. We turn the tables and give you the product. In the space provided show the starting material required to make that product using the given reagents. When more than one starting material would work, you must draw both.
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following:  (e) Dilute sulfuric acid 
Write the structure of the major organic product formed in the reaction of 2-methyl-2-butene with each of the following: (e) Dilute sulfuric acid 
Illustrate the mechanism for the following reaction. Indicate all arrows and structures of intermediates.
In a widely used industrial process, the mixture of ethylene and propene that is obtained by dehydrogenation of natural gas is passed into concentrated sulfuric acid. Water is added, and the solution is heated to hydrolyze the alkyl hydrogen sulfate. The product is almost exclusively a single alcohol. Is this alcohol ethanol, 1-propanol, or 2-propanol? Why is this particular one formed almost exclusively?   
What is the major product from the reaction shown?
Write the structure of the major organic product formed in the reaction of 1-methylcyclohexene with each of the following: (e) Dilute sulfuric acid
Identify the nucleophile that attacks the carbocation intermediate in the acid-catalyzed hydration shown. 
Create the full arrow pushing mechanism which shows all intermediates and all products that result from these reactions and label minor and major products if they are not equal in potential energy.
Provide a detailed mechanism for the following reaction using a curved arrow notation. 
Which of the following molecules would be produced from the reaction below?
The acid catalyzed addition of water to alkenes is a common method to prepare alcohols. For the example below, show the mechanism of this reaction. Include all flows of electrons, charges and intermediates. The mechanism MUST show how the acid is catalytic.
Give three examples of acid-catalyzed reactions. For each example clearly indicate the starting material, reagents and products.
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate, if stereoisomers are produced draw one and state the relationship between the other stereoisomer formed. (enantiomers, diastereomers, etc.).
Write a mechanism for the following reaction.
On the basis of the mechanism of acid-catalyzed hydration, can you suggest why the reaction would probably not be a good method for the synthesis of 3-methyl-2-butanol?
Deuterium oxide (D2O) is water in which the protons (1H) have been replaced by their heavier isotope deuterium (2H). It is readily available and is used in a variety of mechanistic studies in organic chemistry and biochemistry. When D2O is added to an alcohol (ROH), deuterium replaces the proton of the hydroxyl group.ROH + D2O ⇌ ROD + DOH  The reaction takes place extremely rapidly, and if D2O is present in excess, all the alcohol is converted to ROD. This hydrogen–deuterium exchange can be catalyzed by either acids or bases. If D3O+ is the catalyst in acid solution and DO- the catalyst in base, write reasonable reaction mechanisms for the conversion of ROH to ROD under conditions of (a) acid catalysis and (b) base catalysis.  
Read these directions carefully. (It was worth repeating) For the reaction of an alkene with water and a small amount of sulfuric acid shown below, fill in the details of the mechanism. Draw the appropriate chemical structures and use an arrow to show how pairs of electrons are moved to make and break bonds during the reaction. For this question, you must draw all molecules produced in each step (yes, these equations need to be balanced!). Finally, fill in the boxes adjacent to the arrows with the type of step involved, such as "Make a bond" or Take a proton away". MAKE SURE TO NOTICE THE QUESTIONS AT THE BOTTOM. If an intermediate or product is chiral, you only need to draw one enantiomer for this problem.During the reaction described by the above mechanism, what happens to the pH of the solution ________________________________Is this reaction catalytic in acid? ___________________________________________One of the above steps involves making a bond between a nucleophile and an electrophile. Draw a circle around the electrophile.
Predict the products of the following reaction. Show stereochemistry when applicable.  
The following reactions all involve chemistry of alkenes. Fill in the box with the product(s) that are missing from the chemical reaction equations. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES.
Predict the product:
Supply Reagents:
Provide the mechanism for the following reaction. Be sure to include all intermediates, formal charges and arrows depicting electron movement.
Predict the major product(s) :
Please provide the full arrow-pushing mechanism for this reaction. Include stereochemistry for the final product if applicable. 
Complete the following reaction by supplying the missing reactant.
Predict the organic product of the following reaction: 
Give the major organic product(s) for the following reaction
Draw the alkene that would react with the reagent given to account for the product formed. • You do not have to consider stereochemistry.  • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.
Give the major organic product of the following reaction. 
What type of alcohol is formed by the hydration of 2-butene?a. primaryb. secondaryc. tertiaryd. none of these, the product is not an alcohol
Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. 
Which of the following reagents could be used in the reaction below? a. H3O+ b. KOH and HCI c. BH3, H2O2, NaOH d. H2 and H2O
Complete the following reaction by drawing the structure of the major product(s) expected.
Draw the two alkenes that give rise to the following alcohol as the major product of acid-catalyzed hydration.
Predict the product of the following reaction and include hydrogen atoms in your structure:
Give the major organic product(s) for the following reaction.  
Predict the neutral product of the following reaction.
Draw the structure of the product that is expected when the following compound is treated with concentration H2SO4. If more than one product is possible, draw the structure of the minor product. • You do not have to consider stereochemistry.• You do not have to explicitly draw H atoms.   
Give the product of the following reaction. 
What is the major organic product obtained from the following reaction?