Concept explainers
Interpretation:
The structures of the major organic products formed in the reaction of
Concept introduction:
When an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogens, and the halogen adds to the carbon that has fewer hydrogens. This rule is called Markovnikov’s rule.
During hydroboration oxidation, hydrogen forms a bond with the carbon atom that has fewer hydrogens attached to it and the hydroxyl atom forms a bond with the carbon atom that has a greater number of hydrogens attached to it. This is a rule opposite to the Markovnikov’s addition.
Answer to Problem 28P
Solution:
Explanation of Solution
(a) Reaction of
The given alkene,
Hydrogen chloride gets added to the double bond of
(b) Reaction of
This reaction is an acid catalyzed electrophilic addition reaction of alkenes in which water molecule adds to the double bond in
A molecule of water adds to the double bond of
The addition mechanism for this reaction follows the Markovnikov’s rule. Therefore, the major organic product for the above acid-catalyzed electrophilic addition reaction is
(c) Reaction of
Hydroboration-oxidation leads to the overall hydration of an alkene. In hydroboration-oxidation,
The hydrogen atom in the water molecule adds to the carbon
In case of
(d) Reaction of
Bromine reacts rapidly with alkenes by electrophilic addition. The products are called vicinal dibromides, meaning that the bromine atoms get attached to adjacent double bonded carbon atoms. It is carried out in suitable solvents like
A molecule of bromine adds across the double bond in
(e) Reaction of
Chlorine and bromine react with alkenes in aqueous solution to give the corresponding vicinal halohydrins – compounds that add a halogen and hydroxyl group on adjacent carbon atoms in the alkene. The halogen atom forms a bond with that carbon atom in alkene, which has a greater number of hydrogen atoms, while the hydroxyl group bonds to that carbon atom in alkene, which has a fewer number of hydrogen atoms.
In the reaction of
(f) Reaction of
Peroxyacid transfers oxygen to the double bond of alkene to yield epoxides, which is a three-membered oxygen-containing ring.
When
(g) Reaction of
Ozone is a powerful electrophile and reacts with alkenes to cleave the double bond between two oxygen atoms in the molecule, forming an ozonide.
When
(h) Product of part (g) treated with zinc in water
Ozonides are formed as a result of the reaction of ozone with an alkene. Ozonides undergo hydrolysis in water giving carbonyl compounds. Depending upon the structure of the starting alkene, various carbonyl compounds such as formaldehyde, aldehydes, or ketones are formed.
When corresponding ozonide of
(i) Product of part (g) is treated with dimethyl sulfide.
Ozonides are formed as a result of the reaction of ozone with an alkene. Ozonides undergo hydrolysis in water, giving carbonyl compounds. Depending upon the structure of the starting alkene, various carbonyl compounds such as formaldehyde, aldehydes, or ketones are formed.
When corresponding ozonide of
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Chapter 8 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning