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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 products (Q) and (R ), respectively, are:

A

B

C

D

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The correct Answer is:
To solve the problem step by step, we need to identify the structures of the compounds P, Q, R, and S based on the given reactions and tests. ### Step 1: Identify Compound P - **Given Information**: Compound P is a carbonyl compound that gives a positive iodoform test. - **Analysis**: The iodoform test is positive for compounds that have a methyl ketone (a carbonyl group adjacent to a CH3 group) or ethanol. Therefore, P must be a methyl ketone. - **Structure of P**: The simplest methyl ketone is acetone (CH3COCH3). ### Step 2: Reaction of P with MeMgBr - **Reaction**: P (acetone) reacts with methyl magnesium bromide (MeMgBr), which is a Grignard reagent. - **Mechanism**: The Grignard reagent adds to the carbonyl carbon of acetone, forming a tertiary alcohol after hydrolysis. - **Product Q**: The product after the reaction and subsequent dehydration (removal of water) will be an alkene. In this case, the product will be 2-methylpropene (isobutylene). ### Step 3: Ozonolysis of Q - **Reaction**: Q (2-methylpropene) undergoes ozonolysis, which cleaves the double bond and forms carbonyl compounds. - **Product R**: The ozonolysis of 2-methylpropene will yield two carbonyl compounds: acetaldehyde (CH3CHO) and acetone (CH3COCH3). However, since we are looking for a dicarbonyl compound, we can consider the product to be 3-oxobutan-2-one (which has two carbonyl groups). ### Step 4: Intramolecular Aldol Reaction of R - **Reaction**: The dicarbonyl compound R (3-oxobutan-2-one) undergoes an intramolecular aldol reaction. - **Mechanism**: In this reaction, one of the carbonyl groups acts as an electrophile, while the adjacent carbon with an alpha hydrogen acts as a nucleophile, leading to the formation of a cyclic compound. - **Product S**: The predominant product S from this reaction will be 2,5-dimethyl-2,5-dihydro-3-furanone. ### Summary of Products - **P**: Acetone (CH3COCH3) - **Q**: 2-methylpropene (isobutylene) - **R**: 3-oxobutan-2-one (dicarbonyl compound) - **S**: 2,5-dimethyl-2,5-dihydro-3-furanone ### Final Answer The structures of products (Q) and (R) are: - **Q**: 2-methylpropene (isobutylene) - **R**: 3-oxobutan-2-one
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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 product (S) is:

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:

underset((ii) Zn-H_(2)O) overset((i) O_(3))to underset(Delta) overset(bar:OH)to NO. of aldol condensation product.

But-2-ene underset(2.Zn,H_(2)O)overset(1.O_(3))(to)Punderset(Delta)overset(OH^(Ө))(to)Qunderset(H_(2))overset(Pd//C)(to)R R is :

(CH_(3))_(2)COoverset(NaCN)underset(HCI)rarr(A)underset(Delta)overset(H_(3)^(+)O)rarr(B) In the above sequence of reactions, (A) and (B) are :

C_(6)H_(15)O_(6)(P) underset(Zn, H_(2)O)overset(O_(3))rarrC_(4)H_(8)O_(4)(Q) underset("reagent")overset("Molish")rarr Violet colour ring Structure of P connote be :

H-C-=C-H underset(H_(2)SO_(4))overset(HgSO_(4))(rarr)overset("dil.NaOH")(rarr)overset(Delta)(rarr)P . The final product P is

+Cl-CH_(2)CH_(2)CH_(3)overset(AlCl_(3))(rarr) P underset((ii)H_(2)O)overset((i)O_(2)//Delta)(rarr)Q+ Phenol The major products P and Q are :

Benzene +Cl-CH_(2)CH_(2)CH_(3)overset(AlCl_(3))(rarr) P underset((ii)H_(2)O)overset((i)O_(2)//Delta)(rarr)Q+ Phenol The major products P and Q are :

C_(2)H_(2) underset( H_(2)SO_(4))overset( Hg(OH)_(2) 1%) (rarr) A overset( [O])(rarr) B , B is :

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

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

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

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

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

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

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

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

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  12. In the following reaction Compound X is :

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  13. In the following reactoins The major compound Y is

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  14. Positive Tollen's test is observed for

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  15. The major product of the following reaction sequence is

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

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

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

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

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

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