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Exercise · Q45

Q.Read the following reaction and answer the questions given below.
CH3-C(CH3)=CH2 + HBr --benzoyl peroxide--> CH3-CH(CH3)-CH2Br
a. Write IUPAC name of the product.
b. State the rule that governs formation of this product.

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Step 1. Identify the reaction. CH3-C(CH3)=CH2 (2-methylprop-1-ene) plus HBr, with benzoyl peroxide present, is the anti-Markovnikov (peroxide effect) addition of section 15.2.4.

Step 2. Work out the regiochemistry. Peroxide reverses the usual Markovnikov placement: instead of Br going to the more-substituted carbon (which would give the tertiary bromide, 2-bromo-2-methylpropane), Br goes to the LESS-substituted, terminal carbon, giving CH3-CH(CH3)-CH2Br.

Step 3. Name the product. CH3-CH(CH3)-CH2-Br, numbered for the lowest locant, is 1-bromo-2-methylpropane. …

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