18.1: Summary of Important Topics for Alkynes and Alkyne Chemistry

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1. NOMENCLATURE - Refer to section 9-2 of the textbook for IUPAC and common names, and to the chart of functional group order of precedence on page 2 of this manuscript.

2. ACID-BASE REACTIONS OF TERMINAL ALKYNES - Refer to section 9-6 of the textbook, including 9-6A and 9-6B.

The acetylide ion can be used as a strong base or nucelophile.

3. USING ACETYLIDE IONS AS CARBON NUCLEOPHILES - Carbon nucleophiles are used for carbon chain expansion by creating new carbon-carbon bonds. In this chapter they are used in Sn2 reactions to make internal alkynes, and in reactions with carbonyl compounds to make alcohols.

(a) SYNTHESIS OF INTERNAL ALKYNES BY Sn2 REACTIONS (Sect. 9-6A).

(b) SYNTHESIS OF ALCOHOLS BY NUCLEOPHILIC ADDITION TO CARBONYL COMPOUNDS (Sect. 9-7B).

4. ADDITION OF ELECTROPHILES TO THE CARBON-CARBON TRIPLE BOND - Similar to addition of electrophiles to the carbon-carbon double bond, with some differences (Sect. 9-9A to 9-9F).

5. OXIDATION REACTIONS OF THE CARBON-CARBON TRIPLE BOND - Similar to oxidation reactions of the carbon-carbon double bond, with some differences (Sect. 9-10).