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Ch. 2 - Acids and Bases; Functional Groups
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 2, Problema 51a

In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.
(a)

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Step 1: Identify the reactants in the given reaction. We have dimethylamine ((CH3)2NH) and hydrochloric acid (HCl).
Step 2: Determine the role of each reactant. Dimethylamine ((CH3)2NH) has a lone pair of electrons on the nitrogen atom, making it a Lewis base (nucleophile). Hydrochloric acid (HCl) can donate a proton (H+), making it a Lewis acid (electrophile).
Step 3: Use curved arrows to indicate the movement of electron pairs. The lone pair on the nitrogen atom of dimethylamine will attack the hydrogen atom of HCl, forming a bond between nitrogen and hydrogen.
Step 4: Draw the nonbonding electrons. After the nitrogen atom donates its lone pair to form a bond with hydrogen, the nitrogen will have a positive charge, resulting in (CH3)2(+NH2). The chloride ion (Cl-) will have a full octet and a negative charge.
Step 5: Review the electron movement and charges. The curved arrow should start from the lone pair on nitrogen and point towards the hydrogen atom in HCl, indicating the formation of a new N-H bond and the generation of Cl- as a byproduct.

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Lewis Acids and Bases

Lewis acids are species that accept electron pairs, while Lewis bases donate electron pairs. In the given reaction, HCl acts as a Lewis acid because it accepts an electron pair from (CH3)2NH, which acts as a Lewis base by donating an electron pair.
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The Lewis definition of acids and bases.

Electrophiles and Nucleophiles

Electrophiles are electron-deficient species that seek electrons, whereas nucleophiles are electron-rich species that donate electrons. In the reaction, HCl is the electrophile as it seeks electrons, and (CH3)2NH is the nucleophile as it donates electrons to form a bond.
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Nucleophile or Electrophile

Curved Arrow Notation

Curved arrows are used in organic chemistry to depict the movement of electron pairs during reactions. In this reaction, a curved arrow would show the electron pair from the nitrogen in (CH3)2NH moving towards the hydrogen in HCl, indicating the formation of a new bond and the generation of (CH3)2(+NH2) and Cl-.
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Alternative MO Notation for Dienes
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