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A carbonyl compound (P) which gives posi...

A carbonyl compound (P) which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to give an olefin (Q). Ozonolysis of (Q) leads to a dicarbonyl compound (R ) which undergors intramolecular aldol reaction to give predominantly (S).
`Poverset(1. MeMgBr)underset{:(2.H^(+)","H_(2)O),(3.H_(2)SO_(4)","Delta):}rarr Q underset(2. Zn"," H_(2)O)overset(1. O_(3))rarr R underset(2. Delta)overset(1. OH^(-))rarr S`
The structure of product (S) is:

A

B

C

D

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To solve the problem step by step, we will analyze the transformations of the carbonyl compound (P) through to the final product (S). ### Step 1: Identify Compound P - **Given Information**: Compound P is a carbonyl compound that gives a positive iodoform test. - **Conclusion**: This indicates that P must be a methyl ketone (or a compound that can be oxidized to a methyl ketone). A common example is 2-butanone (CH3COCH2CH3). ### Step 2: Reaction with MeMgBr - **Reaction**: P reacts with methyl magnesium bromide (MeMgBr), which is a Grignard reagent. - **Mechanism**: The Grignard reagent adds to the carbonyl carbon of P, forming an alcohol after hydrolysis. - **Resulting Compound Q**: For 2-butanone, the reaction would yield 2-butanol (CH3C(OH)(CH3)CH2CH3). ### Step 3: Dehydration to Form Olefin Q - **Dehydration**: The alcohol (Q) undergoes dehydration (loss of water) to form an alkene. - **Resulting Olefin Q**: From 2-butanol, dehydration would yield butene (specifically, 2-butene). ### Step 4: Ozonolysis of Olefin Q - **Reaction**: Ozonolysis of Q (2-butene) involves treating it with ozone (O3), followed by reduction. - **Resulting Compound R**: Ozonolysis of 2-butene would yield two molecules of acetaldehyde (CH3CHO), which is a dicarbonyl compound. ### Step 5: Intramolecular Aldol Reaction of R - **Aldol Reaction**: The dicarbonyl compound (R) undergoes an intramolecular aldol reaction. This requires at least one carbonyl and alpha hydrogens. - **Mechanism**: The aldehyde group reacts with the alpha hydrogen of the other carbonyl group, forming a six-membered ring. - **Resulting Compound S**: The product of this reaction is likely to be a cyclic compound, specifically 2-methyl-2-cyclopentene-1, which is predominantly formed. ### Final Structure of Product S - The final product (S) can be represented as a cyclic compound with the structure: - A six-membered ring with a double bond and two methyl groups attached. ### Summary of Steps 1. Identify P as a methyl ketone (e.g., 2-butanone). 2. React P with MeMgBr to form an alcohol (Q). 3. Dehydrate Q to form an olefin (2-butene). 4. Perform ozonolysis on Q to yield a dicarbonyl compound (R). 5. Conduct an intramolecular aldol reaction on R to yield the final product (S).
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A carbonyl compound (P) which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to give an olefin (Q). Ozonolysis of (Q) leads to a dicarbonyl compound (R ) which undergors intramolecular aldol reaction to give predominantly (S). Poverset(1. MeMgBr)underset{:(2.H^(+)","H_(2)O),(3.H_(2)SO_(4)","Delta):}rarr Q underset(2. Zn"," H_(2)O)overset(1. O_(3))rarr R underset(2. Delta)overset(1. OH^(-))rarr S The structure of products (Q) and (R ), respectively, are:

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ALLEN-ALKENE, ALKANE & ALKYNE -EXERCISE-5[B]
  1. A carbonyl compound (P) which gives positive iodoform test, undergoes ...

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  2. A carbonyl compound (P) which gives positive iodoform test, undergoes ...

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  3. A carbonyl compound (P) which gives positive iodoform test, undergoes ...

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  4. An acyclic hydrocarbon P, having molecular fromula C(6)H(10) gave acet...

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  5. An acyclic hydrocarbon P, having molecular fromula C(6)H(10) gave acet...

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  6. The number of aldol reaction(s) that occurs in the given transformatio...

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  7. Among P,Q,R and S, the aromatic compound(s) is/are

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  8. After completion of the reactions (I and II), the organic compounds in...

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  9. Consider all possible isomeric ketones, including stereoisomers, of MW...

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  10. The major product in the following reaction is underset(2. " a...

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  11. In the following reaction Compound X is :

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  12. In the following reactoins The major compound Y is

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  13. Positive Tollen's test is observed for

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  14. The major product of the following reaction sequence is

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  15. The major product of nitration of benzoc acid is :

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  16. Identify the final product (Z) in the following sequence of reactions....

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  17. Which of the following carboxylic acids undergoes decarboxylation easi...

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  18. The molecular weight of benzoic acid in benzene as determined by depre...

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  19. CH(3)CH(2)COOHoverset(Br(2)//P)toAoverset("excess of "NH(2))toY. The...

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  20. Which of the following compounds is most susceptible to a nucleophilic...

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