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Chapter 5: Problem 22

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

Short Answer

Expert verified
Answer: The structure of compound A is \(\mathrm{CH}_{3} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{COCH}_{3}\) (hexanedial), and the structure of compound B is 3-methylcyclohexanone.

Step by step solution

01

1. Ozonolysis of cyclohexene

Ozonolysis of cyclohexene breaks the double bond and forms two carbonyl groups. The product of ozonolysis in this case should be hexanedial, which has the following structure: \(\mathrm{OHC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CHO}\)
02

2. Aldol cyclization and acidification

Now, we need to perform aldol cyclization by treating hexanedial with \(\mathrm{NaOH}\). Aldol cyclization is a reaction between carbonyl compounds, and in this case, hexanedial will undergo intramolecular cyclization to form a 6-membered ring. Then, we must acidify the reaction under warm conditions to form compound B. Our aldol product is: \(\mathrm{O}\mathrm{C}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CH}\mathrm{OH}\) Upon acidification, we get compound B, which is our final product: 3-methylcyclohexanone Therefore, the correct answer should be (a) \(\mathrm{CH}_{3} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{COCH}_{3}\) and 3-methylcyclohexanone.

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Most popular questions from this chapter

O=C1C=CCCC1 O=C1CCCCC1 (ii) \(\mathrm{H}_{3} \mathrm{O}^{+} /\). O=C1C=CCCC1=C1CCCCC1 (i)(X) The reagent (X) required is (a) \(\mathrm{NaOH}\) (b) \(\mathrm{I}_{2} / \mathrm{NaOH}\) (c) KCN (d) \(\mathrm{CF}_{3} \mathrm{CO}_{3} \mathrm{H}\)

If (b) is 2 - chloro ethanol, then (A) is (a) 2 - chloro propanal (b) chloro propanal (c) chloro propanone (d) chloro ethanal

(a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONHCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CONH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N}\left(\mathrm{CH}_{3}\right)_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CON}\left(\mathrm{CH}_{3}\right)_{2}\)

O=C1C=CCCC1Cl The IUPAC name of (a) 2 -chlorocyclohex-5-en-1-one (b) 6 -chlorocyclohex-2-en-1-one (c) 4 -chloro-3-oxocyclohex-l-ene (d) 1 -chloro-2-oxocyclohex-3-ene

The reaction \(\left.\left.\right|_{\text {CHO }} ^{\text {CHO }} \stackrel{\mathrm{NaOH}}{\longrightarrow}\right|_{\text {COONa }}{\text { CH }_{2} \mathrm{OH}}\) is an example of (a) intramolecular aldol condensation (b) mixed Cannizzaro reaction (c) intramolecular Cannizzaro reaction (d) crossed Cannizzaro reaction \(\Omega\)
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