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Name the following
a)
Interpretation:
The name of the alkene shown to be given. The products of its reaction with 1) meta-chloroperoxybenzoic acid, 2) KMnO4 in aqueous acid and 3) O3, followed by Zn in acetic acid, are to be given.
Concept introduction:
When alkenes react with meta-chloroperoxybenzoic acid, oxygen atom adds to the double bond to give epoxides.
Upon treatment with KMnO4 in aqueous acid, if the alkene the double bonded carbon is di-substituted and has no hydrogen it is converted in to a ketone and if the double bonded carbon is mono-substituted and has one hydrogen it is oxidized to a carboxylic acid.
Upon treatment with O3, followed by Zn in acetic acid the double bond is cleaved and each carbon in the double bond gets attached to an oxygen atom to give carbonyl compounds as products. If in the alkene double bonded carbon is di-substituted and has no hydrogen it is converted in to a ketone and if the double bonded carbon is mono-substituted and has one hydrogen it is oxidized to an aldehyde.
To give:
The name of the alkene shown and the products of its reaction with 1) meta-chloroperoxybenzoic acid, 2) KMnO4 in aqueous acid and 3) O3, followed by Zn in acetic acid.
Answer to Problem 22VC
The name of the alkene shown is 2,5-dimethyl-2-heptene.
The product formed when it reacts with meta-chloroperoxybenzoic acid is
The products formed when it reacts with KMnO4 in aqueous acid are
The products formed when it reacts with O3, followed by Zn in acetic acid are
Explanation of Solution
2,5-dimethyl-2-heptene has a double bond between C2&C3. When treated with meta-chloroperoxybenzoic acid, oxygen atom adds to both C2&C3 to give an epoxide.
In 2,5-dimethyl-2-heptene, C2 has no hydrogens attached. So it is oxidized to a ketone.C3 has one hydrogen and is oxidized to a carboxylic acid.
Upon treatment with O3, followed by Zn in acetic acid the double bond between C2&C3 in 2,5-dimethyl-2-heptene is cleaved and each carbon gets attached to an oxygen atom to give a ketone and aldehyde as products.
The name of the alkene shown is 2,5-dimethyl-2-heptene is
The product formed when it reacts with meta-chloroperoxybenzoic acid is
The products formed when it reacts with KMnO4 in aqueous acid are
The products formed when it reacts with O3, followed by Zn in acetic acid are
b)
Interpretation:
The name of the alkene shown to be given. The products of its reaction with 1) meta-chloroperoxybenzoic acid, 2) KMnO4 in aqueous acid and 3) O3, followed by Zn in acetic acid, are to be given.
Concept introduction:
When alkenes react with meta-chloroperoxybenzoic acid, oxygen atom adds to the double bond to give epoxides.
Upon treatment with KMnO4 in aqueous acid, if in the alkene double bonded carbon is di-substituted and has no hydrogen it is converted in to a ketone and if the double bonded carbon is mono-substituted and has one hydrogen it is oxidized to a carboxylic acid.
Upon treatment with O3, followed by Zn in acetic acid the double bonded is cleaved and each carbon in the double bond gets attached to an oxygen atom to give carbonyl compounds as products. If in the alkene double bonded carbon is di-substituted and has no hydrogen it is converted in to a ketone and if the double bonded carbon is mono-substituted and has one hydrogen it is oxidized to an aldehyde.
To give:
The name of the alkene shown and the products of its reaction with 1) meta-chloroperoxybenzoic acid, 2) KMnO4 in aqueous acid and 3) O3, followed by Zn in acetic acid.
Answer to Problem 22VC
The name of the alkene shown is 3,3-dimethylcyclopentene.
The product formed when it reacts with meta-chloroperoxybenzoic acid is
The products formed when it reacts with KMnO4 in aqueous acid are
The products formed when it reacts with O3, followed by Zn in acetic acid are
Explanation of Solution
3,3-dimethylcyclopentene has a double bond between C1&C2. When treated with meta-chloroperoxybenzoic acid, oxygen atom adds to both C1&C2 to give an epoxide.
In 3,3-dimethylcyclopentene both C1&C2 have one hydrogen attached to them. So they are oxidized to carboxylic acids when treated with KMnO4.
Upon treatment with O3, followed by Zn in acetic acid the double bond between C1&C2 in 3,3-dimethylcyclopentene is cleaved and each carbon with one hydrogen gets attached to an oxygen atom to yield a dialdehyde as product.
The name of the alkene shown is 3,3-dimethylcyclopentene.
The products formed when it reacts with meta-chloroperoxybenzoic acid are
The products formed when it reacts with KMnO4 in aqueous acid are
The products formed when it reacts with O3, followed by Zn in acetic acid are
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Chapter 8 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
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Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning