Self Test 4.1B

[Fengting Liang 1F]

In the green organic chem textbook on pg. 147:
(Since there is no answer in the book could someone explain how to get the answer to me? I just want to make sure I have the right concept)

What type of reactant is cyanide? Draw its Lewis structure and comment on how it can react. What is the hybridization of the carbon and nitrogen atoms?

I get that it's a nucleophile and how to draw its Lewis structure and get its hybridization, but can someone explain "how it can react?" Thanks!

[Jonathan Sarquiz 3F]

Answers to all Self-Test questions are in the back of the book. 4.1B is found on page 207

But to answer your question about how it reacts: cyanide acts a nucleophile in the reaction. If you look at the formal charge it's actually ^-CN where the carbon has the negative formal charge. Therefore while cyanide is a nucleophile as a whole, it is that negatively charged carbon (not the nitrogen) that is more likely to be the atom involved in the formation of a new bond.