Cyclohexene undergoes ozonolysis in presence of (CH3)2 S to give (A). This undergoes aldol cycl

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Cyclohexene undergoes ozonolysis in presence of (CH3)2 S to...

Cyclohexene undergoes ozonolysis in presence of $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{~S}$ to give (A). This undergoes aldol cyclizaton in $\mathrm{NaOH}$ followed by acidification in warm conditions to give (B). (a) and (b) are respectively, (a) $\mathrm{CH}_{3} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{COCH}_{3}$ and 3 -methylcyclohexanone (b) $\mathrm{OHC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CHO}$ and 3 -methylcyclo-hexanone (c) $\mathrm{OHCCH}_{2} \mathrm{COCH}_{3}$ and (d) $\mathrm{OHC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CHO}$ and

Cyclohexene undergoes ozonolysis in presence of $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{~S}$ to give (A). This undergoes aldol cyclizaton in $\mathrm{NaOH}$ followed by acidification in warm conditions to give (B). (a) and (b) are respectively,
(a) $\mathrm{CH}_{3} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{COCH}_{3}$ and 3 -methylcyclohexanone
(b) $\mathrm{OHC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CHO}$ and 3 -methylcyclo-hexanone
(c) $\mathrm{OHCCH}_{2} \mathrm{COCH}_{3}$ and
(d) $\mathrm{OHC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CHO}$ and

Key Concepts

Intramolecular Cyclization (Aldol Cyclization)

Intramolecular cyclization via the aldol reaction occurs when a molecule containing two carbonyl groups reacts with itself under basic conditions to form a ring structure. Under controlled conditions and often upon acidification, the intermediate formed through the aldol addition undergoes cyclization to yield cyclic compounds, such as cyclohexanones.

Aldol Reaction

The aldol reaction is a carbon–carbon bond-forming process where an enolate ion, generated from a carbonyl compound under basic conditions, attacks another carbonyl group. This reaction typically forms a ?-hydroxyalkyl carbonyl compound that can further dehydrate to yield an ?,?-unsaturated carbonyl compound.

Ozonolysis

Ozonolysis is an organic reaction where ozone (O?) cleaves carbon–carbon double bonds in alkenes to form carbonyl compounds such as aldehydes and ketones. In the reaction, the alkene is initially converted to an ozonide, which is then subjected to a reductive workup (e.g., using dimethyl sulfide) to generate the final carbonyl products without further oxidation.

Reductive Workup

A reductive workup in ozonolysis involves the use of a reducing agent like dimethyl sulfide to break down the intermediate ozonide into stable carbonyl compounds. This step is crucial to prevent over-oxidation and to ensure that aldehydes and ketones are obtained as the final products.

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