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Concept explainers
Interpretation:
Structures of the major organic products formed in the reaction of each of the given reagents with
Concept introduction:
Since
According to Markovnikov’s rule. when an unsymmetrically substituted alkene reacts with a hydrogen halide, hydrogen adds to the carbon that has the greater number of hydrogens and halogen adds to the carbon that has fewer hydrogens.
In a hydroboration oxidation reaction, hydrogen atom gets bonded to the carbon that has fewer hydrogens and the hydroxyl to the carbon that has a greater number of hydrogens. This is a rule opposite of Markovnikov’s addition.
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Answer to Problem 29P
Solution:
a)
b)
c)
d)
e)
f)
g)
h)
i)
Explanation of Solution
a) The reaction is as follows:
The given alkene
Hydrogen chloride adds to the double bond of
b) The reaction is as follows:
This reaction is an acid catalyzed electrophilic addition reaction of alkenes. In this reaction, water molecule gets added to the double bond in
In this reaction, the addition of water molecule to alkene follows Markovnikov’s rule. The hydrogen atom in water molecule adds to the carbon
The addition mechanism for this reaction follows Markovnikov’s rule, and so the major organic product for the above acid-catalyzed electrophilic addition reaction is
c) The reaction is as follows:
This reaction is the hydroboration-oxidation reaction of alkenes. In this reaction, water molecule gets added to the double bond in
The hydrogen atom from water molecule adds to the carbon
d) The reaction is as follows:
Bromine reacts rapidly with alkenes by electrophilic addition. The products are called vicinal dibromides, meaning that the bromine atoms are attached to adjacent double bonded carbon atoms. It is carried out in suitable solvents such as
Bromine adds across the double bond in
e) The reaction is as follows:
In aqueous solution, chlorine and bromine react with alkenes to give corresponding vicinal halohydrins. Halohydrin compounds have a halogen and hydroxyl group on adjacent carbon atoms. In alkene, halogen atom bonds to that carbon atom which has a larger number of hydrogens and hydroxyl group bonds to that carbon atom which has a smaller number of hydrogens.
In the reaction of
f) The reaction is as follows:
Peroxyacids transfers oxygen to the double bond of an alkene to yield epoxides. An epoxide is a three-membered oxygen-containing ring.
When
g) The reaction is as follows:
Ozone is a powerful electrophile and reacts with alkenes to cleave the double bond, forming an ozonide.
h) The reaction is as follows:
Ozonides are formed as a result of the reaction of ozone with an alkene. Ozonides undergo hydrolysis in the water giving carbonyl compounds. According to the structure of starting alkene, various carbonyl products are formed such as formaldehyde, aldehydes, or ketones.
When the corresponding ozonide of
i) The reaction is as follows:
Ozonides are formed as a result of the reaction of ozone with an alkene. Ozonides undergo hydrolysis in water, giving carbonyl compounds. According to the structure of starting alkene, various carbonyl products are formed such as formaldehyde, aldehydes, or ketones.
When corresponding ozonide of
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Chapter 8 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
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