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Chapter 12: PROBLEM 12.19 (page 475)

Question: Draw the products formed when each alkene is treated with O3 followed by Zn, H2O.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Oxidative cleavage

The term oxidative cleavage itself defines the reaction.

Oxidative-addition of oxygen, and cleavage- breaking of carbon-carbon double bond.

In oxidative cleavage, the σ and πbond of alkenes is cleaved, and two C=O (carbonyl bonds are formed).

02

Ozonolysis

Oxidative cleavage using ozone as an oxidizing agent is termed ozonolysis. It is a two-step mechanism where ozonide is formed in the first step, which is converted to carbonyl group using reagents Zn (in water)

03

Oxidative cleavage of compound

Depending on the R groups, aldehyde or ketone products are obtained.

a.

Oxidative cleavage- one aldehyde and one ketone product

b.

Oxidative cleavage- two aldehyde products

c.

Oxidative cleavage- two carbonyl bond formation

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Most popular questions from this chapter

Question:Devise a synthesis of (E)-hex-2-ene from pent-1-ene and any needed organic compounds or inorganic reagents.

Question: Explain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene.

Question: Sodium hypochlorite (NaOCl, the oxidant in household bleach) in aqueous CH3COOH is also touted as a “green” oxidizing agent. For example, oxidation of (CH3)2CHOH with NaOCl forms along with NaCl and H2O. (a) What advantages and/or disadvantages does this method have over oxidation with HCrO4––Amberlyst A-26 resin? (b) What advantages and/or disadvantages does this method have over oxidation with CrO3, H2SO4,H2O.

Question: Label each reaction as oxidation, reduction, or neither.

a.

b.

c.

d.

Question: What alkene is needed to synthesize each 1,2-diol using [1] followed by NAHSO3 in H2O ; or [2] CH3CO3H followed by -OH in H2O ?

a.

b.

c.
See all solutions

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