1
Question
From the list of alkenes given below, identify the alkenes which on reductive ozonolysis given only ketones.
(a) 2-methyl-1-butene
(b) 1-butene
(c) 2,3-dimethyl-2-butene
(d) 3-methyl-2-pentene
(e) 3,4-dimethyl-3-hexene
(f) 2,5-dimethyl-2,4-hexadiene
From the list of alkenes given below, identify the alkenes which on reductive ozonolysis given only ketones.
(a) 2-methyl-1-butene
(b) 1-butene
(c) 2,3-dimethyl-2-butene
(d) 3-methyl-2-pentene
(e) 3,4-dimethyl-3-hexene
(f) 2,5-dimethyl-2,4-hexadiene
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Solution
The correct option is B c and e only
Ozonolysis of alkenes involves the addition of an ozone molecule to an alkene, to form an ozonide. Formed ozonide undergoes cleavage by Zn/H2O to give smaller oxidised product.
(a) 2-methyl-1-buteneCH3CH2C(CH3)=CH2O3−−−−−→Zn/H2OCH3CH2CO(CH3)+CH2O
(b) 1-butene CH3CH2CH=CH2O3−−−−−→Zn/H2OCH3CH2CHO+CH2O
(c) 2,3-dimethyl-2-buteneCH3−(CH3)C=C(CH3)−CH3O3−−−−−→Zn/H2OCH3(CH3)CO+OC(CH3)CH3
(d) 3-methyl-2-penteneCH3−CH=C(CH3)−CH2−CH3→CH3−CH=OC(CH3)−CH2−CH3
(e) 3,4-dimethyl-3-hexeneCH3−CH2−C(CH3)=C(CH3)−CH2−CH3O3−−−−−→Zn/H2OCH3−CH2−C(CH3)=O+O=C(CH3)−CH2−CH3
(f) 2,5-dimethyl-2,4-hexadieneCH3−C(CH3)=CH−CH=C(CH3)−CH3O3−−−−−→Zn/H2OCH3−C(CH3)=O+O=CH−CH=O+O=C(CH3)−CH3
Only (c) and (e) forms ketones. Hence correct option is (b).
Ozonolysis of alkenes involves the addition of an ozone molecule to an alkene, to form an ozonide. Formed ozonide undergoes cleavage by Zn/H2O to give smaller oxidised product.
(a) 2-methyl-1-buteneCH3CH2C(CH3)=CH2O3−−−−−→Zn/H2OCH3CH2CO(CH3)+CH2O
(b) 1-butene CH3CH2CH=CH2O3−−−−−→Zn/H2OCH3CH2CHO+CH2O
(c) 2,3-dimethyl-2-buteneCH3−(CH3)C=C(CH3)−CH3O3−−−−−→Zn/H2OCH3(CH3)CO+OC(CH3)CH3
(d) 3-methyl-2-penteneCH3−CH=C(CH3)−CH2−CH3→CH3−CH=OC(CH3)−CH2−CH3
(e) 3,4-dimethyl-3-hexeneCH3−CH2−C(CH3)=C(CH3)−CH2−CH3O3−−−−−→Zn/H2OCH3−CH2−C(CH3)=O+O=C(CH3)−CH2−CH3
(f) 2,5-dimethyl-2,4-hexadieneCH3−C(CH3)=CH−CH=C(CH3)−CH3O3−−−−−→Zn/H2OCH3−C(CH3)=O+O=CH−CH=O+O=C(CH3)−CH3
Only (c) and (e) forms ketones. Hence correct option is (b).
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