Reactions involving acetylide anions

Question 1

Formation of acetylide anions from terminal alkynes

Answer 1

1. Typical bases used for the reaction are NaNH2 and NaH

Question 2

Reaction of acetylide anions with alkyl halides

Answer 2

1. The reaction follows an Sn2 mechanism

2. The reaction works best with Ch3X and RCH2X

Question 3

Reaction of acetylide anions with epoxides

Answer 3

1. The reaction follows an Sn2 mechanism

2. Ring opening occurs from the back side at the less substituted end of the epoxide