Question

21. (Bonus)Which of the following species is more likely to be an electrophile, and which a nucleophile? Could any of these be both electrophilic AND nucleophilic? If so, which? Write the letter of the species in the correct blank(s). Note: it may be helpful to draw the Lewis structures of each species to better determine the answer. a) NH4 d) CH3NH2 electrophilic? b) CH3OH e) H30* nucleophilic? c) CN f) OH both?

Answer 1

a) NH₄⁺ - Electrophile

b) CH₃OH - Nucleophile

c) CN⁻ - Nucleophile

d) CH₃NH₂ - both

e) H₃O⁺ - Electrophile

Step-by-step explanation:

A nucleophile will have electrons capable of attacking a positive or partially positive atom. Therefore, the higher the electronic density, the better the specie will act as a nucleophile. Both CH₃OH and CN⁻ have high electronic density are likely to be nucleophiles.

An electrophile will have lack electronic density, having more positively charged atoms. Both NH₄⁺ and H₃O⁺ are positively charged and are likely to be electrophiles.

CH₃NH₂ has a more positive carbon and a more negative nitrogen. Therefore, this moleculecould act both as a nucleophile and as an electrophile.

The figure attached shows the lewis structure of the species.