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Chapter 6: Q32P (page 262)

What aspect of the structure of the alkene does ozonolysis not tell you ?

Short Answer

Expert verified

It doesn't say if the double bond is in the E or Z configuration.

Step by step solution

01

Definition of ozonolysis - 

When an alkene is treated with ozone (O3) at a low temperature, the double bond's s and p bonds break, and the carbons that were previously doubly bound to each other are now doubly bonded to oxygens. Because the number of CO bonds rises, this is an oxidation reaction known as ozonolysis.

02

Reductive ozonolysis is the process of converting an alkene into two carbonyl molecules.

We can have cis/trans or E/Z stereochemistry if the R groups are different.

1 is a Z alkene if R2 and R4 are the higher priority groups.

2 is an alkene of the type E.

Both, however, produce the same ozonolysis products.

Reductive ozonolysis cannot discriminate between cis-but-2-ene and trans-but-2-ene.

03

Conclusion-

The only ozonolysis product in both cases is acetaldehyde.

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Most popular questions from this chapter

What hydrocarbon forms the following products after reaction first with ozone and then with dimethyl sulfide?

a. How many s bond orbitals are available for overlap with the vacant p orbital in the methyl cation?

b. Which is more stable: a methyl cation or an ethyl cation? Why?

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?

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.

What will be the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

a. HBr

b. HI

c. Cl2/CH2Cl2

d. O3, −78 °C, followed by (CH3)2S

e. H2/Pd

f. MCPBA (a peroxyacid)

g. H2O + H2SO4

h. Br2/CH2Cl2

i. Br2/H2O

j. Br2/CH3OH

k. BH3/THF, followed by H2O2, HO-, H2O
See all solutions

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