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Chapter 29: Q14P (page 1152)

Question: Identify the nucleophile and the electrophile in the following acid鈥揵ase reactions:

Short Answer

Expert verified

AlCl3is an electrophileand NH3 is a nucleophile.

The H+ of HBr is the electrophile and OH- is the nucleophile.

Step by step solution

01

Definition of Electrophiles

An electrophile is a species that lacks electrons.

"Electrophile" literally translates to "electron loving" (phile is the Greek suffix for "loving"). An electrophile is someone who seeks out a pair of electrons. Electrophiles are easily identifiable because they have a positive charge, a partial positive charge, or an incomplete octet that can accept electrons.

  • AlCl3 is an electrophile because it has an incomplete octet.

H+is an electrophile because it has a positive charge

02

 Definition of Nucleophiles-

A nucleophile is an electron-rich species.

A nucleophile is a non-hydrogen atom that bonds to an electron donor (having an electron pair available for bonding). A base is a hydrogen-bonding electron donor. The alterations that occur when bases or nucleophiles interact are extensive and diverse.

The following compounds are nucleophiles because-

  • NH3and OH- are nucleophiles because they have a pair of electrons to share.

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Most popular questions from this chapter

The enolate derived from diethyl acetamidomalonate is treated with each of the following alkyl halides. After hydrolysis and decarboxylation, what amino acid is formed?

(a)CH3I(b)(CH3)2CHCH2Cl(c)CH3CH2CH(CH3)Br

What form exists at the isoelectric point of each of the following amino acids: (a) valine; (b)leucine; (c)proline; (d) glutamic acid.

Tryptophan is not classified as a basic amino acid even though it has a heterocycle containing a nitrogen atom. Why is the N atom in the five-membered ring of tryptophan not readily protonated by acid?

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly鈥揂la鈥揝er and Ala鈥揝er鈥揂rg

Draw the structure for each peptide:

(a) Phe鈥揂la;

(b) Gly鈥揋ln;

(c) Lys鈥揋ly;

(d) R-H
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