Q 30P - Organic Chemistry (Mcmurry)

Question

What product would you expect from the reaction of 1-phenyl-2-butene with NBS? Explain.

                                 1-phenyl 2-butene

Step-by-Step Solution

Answer

                            Formation of the desired product

Step-by-Step Solution Step 1: 1-phenyl 2-butene

1-phenyl 2-butene reacts with NBS which undergoes radical substitution to form 1-Bromo-1-phenyl-2-butene as the major product.

Step 2: Product formed

The product 1-Bromo-1-phenyl-2-butene is formed because the intermediate free radical giving raise to this product is highly stabilized due to resonance.

                        Formation of the desired product