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Chapter 6: Q31P (page 262)

a. What alkene would give only a ketone with three carbons as a product of oxidative cleavage?

b. What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage?

Short Answer

Expert verified

The conversion of an alkene's carbons into separate carbonyl groups is known as oxidative cleavage.

Step by step solution

01

Definition of oxidative cleavage- 

The conversion of an alkene's carbons into separate carbonyl groups is known as oxidative cleavage.

02

a) 2,3-dimethylbut-2-ene would give only a ketone with three carbons as a product of oxidative cleavage- 

We can figure out what the alkene was by working backwards from the products.

Acetone (CH3)2C=O is the only three-carbon ketone.

Working backwards, we discover that the beginning ingredient has to be 2,3-dimethylbut-2-ene.

03

b) (Z)-oct-4-ene and (E)-oct-4-ene would give only an aldehyde with four carbons as a product of oxidative cleavage-

We can figure out what the alkene was by working backwards from the products.

Aldehyde with four carbons is obtained as a product.

Working backwards, we discover that the beginning ingredient has to be (Z)-oct-4-ene and (E)-oct-4-ene.

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Most popular questions from this chapter

The second-order rate constant (in units of M-1 s-1) for acid-catalysed hydration at 25 掳C is given for each of the following alkenes:

a. Calculate the relative rates of hydration of the alkenes. (Hint: Divide each rate constant by the smallest rate constant of the series: 3.51 脳 10-8.)

b. Why does (Z)-2-butene react faster than (E)-2-butene?

c. Why does 2-methyl-2-butene react faster than (Z)-2-butene?

d. Why does 2,3-dimethyl-2-butene react faster than 2-methyl-2-butene?

What is the product of the addition of I-Cl to 1-butene? (Hint: Chlorine is more electronegative than iodine [Table 1.3].)

When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.

a.What alkene is required to synthesize each of the following compounds?

b. What other epoxide would be formed?

c. Assign an Ror Sconfiguration to each asymmetric center.

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.
See all solutions

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