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

Addition Reaction

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

Now we’re going to discuss a new type of organic mechanism called addition. There’s tons of these to keep track of, so let’s get right into it!

Concept #1: Features of Addition Mechanisms.

Addition reactions are ones in which 1 π-bond is broken and 2 new σ-bonds are formed.

They are the opposite of elimination reactions (if you haven’t learned about these yet don’t worry). 

Example #1: Provide the mechanism for the following addition reaction. 

Additional Problems
Suggest reasonable mechanisms for each of the following reactions. Use curved arrows to show electron fl ow.
The reaction of thiocyanogen (N≡CS—SC≡N) with  cis -cyclooctene proceeds by anti addition. A  bridged  sulfonium ion  is presumed to be an intermediate. Write a stepwise mechanism for this reaction.       
Draw a typical reaction coordinate diagram that best depicts an addition reaction. Briefly provide a rationale.
Which of following statements best describes the general reactivity of alkynes?a) An alkyne reacts as a nucleophile, and is therefore electron poor.b) An alkyne reacts as an electrophile, and is therefore electron poor.c) An alkyne reacts as a nucleophile, and is therefore electron rich.d) Alkynes fail to undergo electrophilic addition reactions, unlike alkenes.e) An alkyne reacts as an electrophile, and is therefore electron rich.
Choose the correct description of the general reaction shown below:1) hydrogenation of an alkene2) bromination of an alkene3) chlorination of an alkene4) hydration of an alkene5) hydrohalogenation of an alkene
Which class of addition reaction is represented by the transformation below? (A) hydration (B) halohydrin formation (C) hydrohalogenation (D) halogenation (E) hydrogenation (F) ozonolysis (G) dihydroxylation
Which class of addition reaction is represented by the transformation below? (A) dihydroxylation (B) hydration (C) halohydrin formation (D) hydrogenation (E) ozonolysis (F) hydrohalogenation (G) halogenation