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

Alkyne Hydration

See all sections
Addition Reaction
Acid-Catalyzed Hydration
Epoxide Reactions
Oxidative Cleavage
Alkyne Oxidative Cleavage
Alkyne Hydrohalogenation
Alkyne Halogenation
Alkyne Hydration
Alkyne Hydroboration
Additional Practice
Thermodynamics of Addition-Elimination Equilibria
Stereospecificity vs. Stereoselectivity
Oxymercuration-Reduction Full Mechanism
Hydroboration-Oxidation Full Mechanism
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

Vinyl alcohols (alcohols directly on a double bond) undergo a process called tautomerization. Don't worry too much about it because we will devote an entire chapter to this process next semester, so you aren’t expected to fully understand it yet.


For now, just memorize what the enol and keto forms look like, so you can predict the products that form when you add alcohol to an alkyne

Concept #1: Vinyl alcohols yield tautomers. 

Both acid-catalyzed hydration and oxymercuration-reduction of any alkyne leads to formation of a ketone. These reactions both yield a Markovnikov vinyl alcohol, which then tautomerizes.  

Concept #2: Markovnikov addition of alcohols yields ketones.   

Additional Problems
For the transformation shown, select the most appropriate reagent(s) to effect the change. a) NaOCl b) H2, Pd c) 1. Disiamylborane, 2. HO –, H2O, H2O2 d) K2Cr2O7, H+ e) H2SO4, HgSO4
What is the final product of the reaction drawn below?
For the reaction shown, which of the compounds below would be expected major, and final, organic product?  
Predict the product for the reaction below. 
Which one of the following alkynes gives a single ketone in the acid-catalyzed hydration of each? a) 2-decyne b) 3-decyne c) 4-decyne d) 5-decyne
Which of the following is the enol intermediate in the acid-catalyzed addition of water to propyne?
Which molecule will correctly complete the reaction shown?
Reaction of an asymmetrical terminal alkyne with mercury sulfate and sulfuric acid in water would produce which of the following?alkenediolaldehydeketone
Propose a detailed mechanism that explains the formation of compound 2 from alkyne 1. (No additional reagents or reactions are needed).
Predict the product(s):
Predict the minor and major products for the following reaction. Hint the products are isomers and in equilbrium with each other. 
Draw the major product of the following reaction. If two organic products are obtained, draw them both. 
Draw the major product(s) expected when each of the following alkynes is treated with aqueous acid in the presence of mercuric sulfate. (HgSO4):
Draw the major product of the following reaction. If two organic product are obtained, draw them both.
Provide the structure of the major organic product that results when 2-butyne is treated with HgSO4/H2SO4 in water. 
Draw the major organic product(s) of the following reactions including stereochemistry when it is appropriate. 
Draw the major organic product(s) of the following reactions including stereochemistry when its appropriate. 
Draw the structure of the product that is formed when the compound shown below undergoes a reaction with H2O in the presence of HgSO4 and H2SO4.
What alkyne that does not contain O is best used to make the compound shown?
Draw the major organic product(s) of the following reactions including stereochemistry when it is appropriate. 
Show how you would carry out the following conversion. Specify the reagents you would use to carry it out. If two or more ways of conversion to the same product are possible, show only one of them.