Products

## Holooly Rewards

We are determined to provide the latest solutions related to all subjects FREE of charge!

Enjoy Limited offers, deals & Discounts by signing up to Holooly Rewards Program

## Holooly Tables

All the data tables that you may search for.

## Holooly Arabia

For Arabic Users, find a teacher/tutor in your City or country in the Middle East.

## Holooly Sources

Find the Source, Textbook, Solution Manual that you are looking for in 1 click.

## Holooly Help Desk

Need Help? We got you covered.

## Q. 6.1

Identifying Electrophiles and Nucleophiles

Which of the following species is likely to behave as a nucleophile and which as an electrophile?

(a) ${NO_2}^{+}$  (b)  $CN^{-}$  (c)  $CH_3NH_2$  (d)  $(CH_3)_3S^+$

S t r a t e g y
A nucleophile has an electron-rich site, either because it is negatively charged or because it has a functional group containing an atom that has a lone pair of electrons. An electrophile has an electron-poor site, either because it is positively charged or because it has a functional group containing an atom that is positively polarized.

## Verified Solution

(a) ${NO_2}^+$ (nitronium ion) is likely to be an electrophile because it is positively charged.

(b) $:C≡N^-$ (cyanide ion) is likely to be a nucleophile because it is negatively charged.

(c) $CH_3NH_2$ (methylamine) might be either a nucleophile or an electrophile depending on the circumstances. The lone pair of electrons on the nitrogen atom makes methylamine a potential nucleophile, while positively polarized N–H hydrogens make methylamine a potential acid (electrophile).

(d) $(CH_3)_3S^+$ (trimethylsulfonium ion) is likely to be an electrophile because it is positively charged.