Reactions and Synthesis

Question: Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:

Question: Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:

(d)  

Question: Which reaction would you expect to be faster, the addition of HBr to cyclohexene or 1-methylcyclohexene? Explain.

Question: What product will result from hydroboration–oxidation of 1-methylcyclopentene with deuterated borane,? Show both the stereochemistry (spatial arrangement) and the regiochemistry (orientation) of the product.

Question: The cis and trans isomers of 2-butene give different cyclopropane products in the Simmons–Smith reaction. Show the structures of both, and

explain the difference.

Question: Predict the products of the following reactions. Don’t worry about the size of the molecule; concentrate on the functional groups.

Question: The addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures of the carbocation intermediate to explain why none of the alternate regioisomers is formed.

Question: How would you carry out the following transformations? Tell what

reagents you would use in each case.

(a)

Question: How would you carry out the following transformations? Tell what

reagents you would use in each case.

(b)

Question: How would you carry out the following transformations? Tell what

reagents you would use in each case.

Show the structures of alkenes that give the following products on oxidative cleavage within acidic solution: 

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution.

Question: Show the structures of alkenes that give the following products on oxidative cleavage with KMnO₄ in acidic solution:

c.

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution:

$a. C{H}_{3}C{H}_{2}C{O}_{2}H + C{O}_2$

Question: Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution 

$b. \left(C{H}_3\right)2C=O +C{H}_{3}C{H}_{2}C{H}_{2}C{O}_{2}H$

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution

$d. CH{}_{3}C{H}_{2}C=OC{H}_{2}C{H}_{2}C{H}_{2}C{H}_{2}C{O}_{2}H$

Question: In planning the synthesis of one compound from another, it’s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Question: In planning the synthesis of one compound from another, it’s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Question: In planning the synthesis of one compound from another, it’s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Question: In planning the synthesis of one compound from another, it’s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Question: Which of the following alcohols could not be made selectively by hydroboration–oxidation of an alkene? Explain.

Question: Which of the following alcohols could not be made selectively by hydroboration–oxidation of an alkene? Explain.

Question: Which of the following alcohols could not be made selectively by hydroboration–oxidation of an alkene? Explain.

Question: Which of the following alcohols could not be made selectively by hydroboration–oxidation of an alkene? Explain.

Question: Plexiglas, a clear plastic used to make many molded articles, is made by polymerization of methyl methacrylate. Draw a representative segment of Plexiglas.

We’ll see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?

We’ll see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?

We’ll see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?