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Chapter 8: Q27P (page 318)

What is the major product of each of the following reactions, assuming that one equivalent of each reagent is used in each reaction?

Short Answer

Expert verified

a) Reactive double bond is that which forms a tertiary carbocation.

Instead of Br being the nucleophile that adds to the tertiary carbon the Pi bond can be nucleophile. in this case stable 6 member ring will be formed. this is expected to be minor product because unlike the publication of the carbocation with Br bond breaking is required to form the product.

b) The double bond is more reactive than the triple bond the reaction forms a new asymmetric centre so a pair of an enantiomer is formed.

It is unlikely that the triple bond will act as a nucleophile because it would have to form an unstable vinylic cation intermediate.

c) The more reactive double bond is the one that forms a tertiary carbocation.

Step by step solution

01

How reaction proceed

a) Reactive double bond is that which forms a tertiary carbocation.

Instead of Br being the nucleophile that adds to the tertiary carbon the Pi bond can be nucleophile. in this case stable 6 member ring will be formed. this is expected to be minor product because unlike the publication of the carbocation with Br bond breaking is required to form the product.

b) The double bond is more reactive than the triple bond the reaction forms a new asymmetric centre so a pair of an enantiomer is formed.

It is unlikely that the triple bond will act as a nucleophile because it would have to form an unstable vinylic cation intermediate.

c) The more reactive double bond is the one that forms a tertiary carbocation.

02

Final answer

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Most popular questions from this chapter

A student wanted to know whether the greater proximity of the nucleophile to the C-2 carbon in the transition state is what causes the 1,2 addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3 cyclohexadiene with HCl. Her friend told her that she should use 1-methyl-1,3 cyclohexadiene instead. Should she follow her friend鈥檚 advice?

a) Propose a mechanism for the following reaction:

b) What is the product of the following reaction?

Which dienophile in each pair is more reactive in a Diels鈥揂lder reaction?

Which diene is more reactive in a Diels鈥揂lder reaction?

Answer the following questions for the molecular orbitals (MOs) of 1,3,5,7-octatetraene:

a. How many MOs does the compound have?

b. Which are the bonding MOs, and which are the antibonding MOs?

c. Which MOs are symmetric, and which are antisymmetric?

d. Which MO is the HOMO and which is the LUMO in the ground state?

e. Which MO is the HOMO and which is the LUMO in the excited state?

f. What is the relationship between HOMO and LUMO and symmetric and antisymmetric orbitals?

g. How many nodes does the highest-energy MO of 1,3,5,7-octatetraene have between the nuclei?

Which compound would you expect to have the greater heat of hydrogenation: 1,2-pentadiene or 1,4-pentadiene?
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