3.10 quiz key

3.10 quiz key - Draw the reaction coordinate diagram and...

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Weekly Quiz March 10, 2006 1. Explain why the reaction of HBr with an alkene is an electrophilic addition reaction. Answer: It is an electrophilic addition reaction b/c the Pi bond serves as the nucleophile and what sparks the reaction is the addition of an electrophile to create the intermediate (in this case a carbocation) that moves forward to form the product. The type of reaction is an addition reaction b/c two molecules come together to give one. 2. Name the following molecules Cl OCH 3 3-chloro-2-methylcyclobutene 5-(methoxymethyl)-6-methyl-2-octene OR 1-methyl-4-chlorocyclobutene (this is correct b/c the branch point is 1 as opposed to 2) 3. Assign stereochemistry to the following double bonds. Cl O H N E Can’t assign 4. What is the Relationship between:
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Br Br Br Br Br A C D E B A and B CONSTITUTIONAL ISOMERS A and C CONFORMERS A and D CIS-TRANS ISOMERS--DIASTEREOMERS A and E ENANTIOMERS 5. What is the result of the reaction of 2-methylpropene with HCl. Draw the potential intermediates and products. Which product is the major product?
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Unformatted text preview: Draw the reaction coordinate diagram and discuss why the major product is both thermodynamically and kinetically favored. The result is either the formation of 2-chloro-2-methylpropane or 1-chloro-2-methylpropane. However, since 2-chloro-2-methylpropane proceeds through a tertiary carbocationit is the major product (in this case, the only product). The reaction coordinate diagram should show the stability of the tertiary carbocation (leading to the formation of 2-chloro-2-methylpropane) at a lower energy (more stable) than the primary carbocation (leading to the formation of 1-chloro-2-methylpropane). The formation of 2-chloro-2-methylpropane is thermodyanically favored. The RCD should also show that the free energy of activation should be lower for formation of the tertiary carbocation and higher for the formation of the primary carbocation. This shows that the formation of 2-chloro-2-methylpropane is kinetically favored....
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3.10 quiz key - Draw the reaction coordinate diagram and...

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