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Chapter 10: Q 30P (page 308)

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

1-phenyl 2-butene

Short Answer

Expert verified

Formation of the desired product

Step by step solution

01

Step-by-Step SolutionStep 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.

02

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

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Most popular questions from this chapter

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (a) Chlorocyclopentane.

Alkylbenzenes such as toluene (methylbenzene) react with NBS to give

products in which bromine substitution has occurred next to the aromatic ring (the benzylic position). Explain, based on the bond dissociation energies in Table 6-3 on page 170.

Question: How strong a base would you expect a Grignard reagent to be? Look at Table 9-1 on page 276, and predict whether the following reactions will occur as written. (The pKaof NH3is 35.)

(b)

Draw three resonance forms for the cyclohexadienyl radical.

Cyclohexadienyl radical

What product(s) would you expect from the reaction of 1,4-hexadiene with NBS? What is the structure of the most stable radical intermediate?
See all solutions

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