Ch. 14 - Synthetic TechniquesSee 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

Alkynide Alkylation

See all sections
Sections
Synthetic Cheatsheet
Moving Functionality
Alkynide Alkylation
Alkane Halogenation
Retrosynthesis

Organometals aren't the only way to create new carbon-carbon bonds. It turns out we can use a sodium alkynide (nucleophile) as well to react with alkyl halides and other electrophiles to form a new C-C bond as well. 

Concept #1: Sodium Alkynide Alkylation

Once we create these triple bond nucleophiles and use them in our synthesis, we will will also learn how to get rid of them and transform them to double bonds (cis and trans) and single bonds.

 

Let's get to work. These will be multi-step transformations. Do your best to see if you can fill in the correct reagents! 

Practice: Propose a synthesis:

Practice: Propose a synthesis:

Additional Problems
Provide the reagents required for the following transformations. Note, that some of these methods will require more than one chemical step. All the steps and reagents must be included.
Provide only the major product for the following synthesis. Stereochemistry is not important.
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms  
For the following sequences of reactions, work through all the different reactions and then write the final product(s). Assume only the predominant product is formed at each step. You must indicate stereochemistry with wedges and dashes. You must draw all stereoisomers produced as predominant products and write "racemic" under the structures when appropriate. Assume no rearrangments take place. You do not need to draw any of the molecules synthesized along the way, just the final product(s).
Give structures for the products of each of the following reactions:  
 Draw the major, neutral organic product(s) for each reaction below 
Write the structural formula of the organic product for the following reaction between an alkyne and an alkyl halide. (The alkyne group is shown, and should be entered, as "CC" without the triple bond.) Product structural formula (formatting counts; enter C before associated H atoms, subscript numbers) (e.g, CH3CH2CH2OCHCHCH3) 
Write the structural formula of the organic product for the following reaction between an alkyne and an alkyl halide. (The alkyne group is shown, and should be entered, as "CC", without the triple bond.)
Draw the structure of the major organic product(s) for the following reaction between an acetylenic anion and an alkyl halide. (The reaction stoichiometry is 1:1.) 
Draw the major, neutral organic product(s) for each reaction below. 
Draw the major product of the following reaction. If two organic products are obtained, draw them both.