We said that regardless of the length of the R group, it's always going to turn into benzoic acid unless you're missing hydrogens. Essentially, 3 of these have a benzylic hydrogen. One doesn't. A has a hydrogen. C has a hydrogen, and D actually has 2 hydrogens. But B has none. So B is the answer. B would actually display no reaction when reacted with KMnO4 because it does not have a benzylic hydrogen available to oxidize. So it's not going to be able to respond to the oxidizing agent. Awesome, guys. Like I said, pretty easy concept. Not much to know. Let's move on to the next one.
19. Reactions of Aromatics: EAS and Beyond
Side-Chain Oxidation
19. Reactions of Aromatics: EAS and Beyond
Side-Chain Oxidation - Online Tutor, Practice Problems & Exam Prep
We know that the alkyl group directly attached to benzene is known as an alkyl side-chain. Now, regardless of the length of that side-chain, it can be oxidized to benzoic acid using hot KMnO4. What's the kicker? There must be at least one benzylic hydrogen.
1
concept
Benzylic Oxidation
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2
example
Which alkylbenzene would NOT yield benzoic acid, treated with KMnO4
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PRACTICE PROBLEMS AND ACTIVITIES (9)
- What products are obtained from the reaction of the following compounds with H2CrO4 + ∆? b.
- What are the products of the following reactions? a. b.
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- Predict the product of the following series of reactions.(a) <IMAGE>
- (••) Suggest the reagents used to effect the transformations shown.(a) <IMAGE>
- (••) Predict the product(s) of the following reactions.(b) <IMAGE>
- Give the structures of compounds C through D in the following series of reactions.<IMAGE>
- Give the structures of compounds A through C in the following series of reactions.<IMAGE>
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