Accedi

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Figure1

With conjugated systems like 1,3-butadiene, the addition of one equivalent of HBr yields a mixture of products: 1,2 and 1,4-addition products. As shown below, the mechanism involves the addition of H+ across one of the double bonds of the conjugated diene to form a resonance stabilized allyl cation. This is followed by the nucleophilic attack of Br at either carbon of the allyl cation bearing a positive charge to form the 1,2 or the 1,4-addition product.

Figure2

The ratio of the products formed depends on the reaction temperature. Low temperature favors the 1,2-adduct, whereas the 1,4-adduct is preferentially formed at higher temperatures.

Tags
12 addition14 additionHydrogen HalidesHBrAlkenesDienes13 butadieneMarkovnikov s RuleAllyl CationResonance StabilizationNucleophilic AttackReaction Temperature

Dal capitolo 16:

article

Now Playing

16.6 : Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

4.6K Visualizzazioni

article

16.1 : Struttura dei dieni coniugati

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

4.2K Visualizzazioni

article

16.2 : Stabilità dei dieni coniugati

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

3.1K Visualizzazioni

article

16.3 : π Orbitali molecolari dell'1,3-butadiene

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

8.0K Visualizzazioni

article

16.4 : π Orbitali molecolari del catione allile e dell'anione

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

3.9K Visualizzazioni

article

16.5 : π Orbitali molecolari del radicale allile

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

3.2K Visualizzazioni

article

16.7 : Addizione elettrofila di X2 a 1,3-butadiene

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

2.2K Visualizzazioni

article

16.8 : Addizione elettrofila di HX all'1,3-butadiene: controllo termodinamico vs controllo cinetico

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

2.3K Visualizzazioni

article

16.9 : Spettroscopia UV-Vis di sistemi coniugati

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

6.6K Visualizzazioni

article

16.10 : Spettroscopia UV-Vis: Regole di Woodward-Fieser

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

22.5K Visualizzazioni

article

16.11 : Reazioni pericicliche: Introduzione

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

7.1K Visualizzazioni

article

16.12 : Reazioni elettrocicliche termiche e fotochimiche: panoramica

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

2.2K Visualizzazioni

article

16.13 : Reazioni Elettrocicliche Termiche: Stereochimica

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

1.9K Visualizzazioni

article

16.14 : Reazioni elettrocicliche fotochimiche: stereochimica

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

1.7K Visualizzazioni

article

16.15 : Reazioni di cicloaddizione: panoramica

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

2.4K Visualizzazioni

See More

JoVE Logo

Riservatezza

Condizioni di utilizzo

Politiche

Ricerca

Didattica

CHI SIAMO

Copyright © 2025 MyJoVE Corporation. Tutti i diritti riservati