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Chapter 6

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.

Step-by-Step

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.