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CH(3)-overset(O)overset(||)C-CH(2)-CH(3)...

`CH_(3)-overset(O)overset(||)C-CH_(2)-CH_(3)+CH_(3)MgBrrarr X overset(H_(3)O^(+))rarr Yoverset(H_(2)SO_(4))underset(170^(@)C)rarr Z.`
What is Z ?

A

`CH_(3)-overset(OH)overset("| ")underset(CH_(3))underset("| ")"C "-CH_(2)-CH_(3)`

B

`CH_(3)-underset(CH_(3))underset("| ")"C "=CH-CH_(3)`

C

`CH_(3)-overset(C_(2)H_(5))overset("| ")underset(CH_(3))underset("| ")"C "-O-overset(C_(2)H_(5))overset("| ")underset(CH_(3))underset("| ")"C "-CH_(3)`

D

`CH_(2)=underset(CH_(3))underset("| ")"C "-CH_(2)-CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given reaction sequence, we will break it down step by step, identifying the products at each stage. ### Step 1: Formation of X We start with the compound: \[ CH_3C(=O)CH_2CH_3 + CH_3MgBr \] This is a reaction between an aldehyde (or ketone) and a Grignard reagent (CH₃MgBr). The Grignard reagent acts as a nucleophile and attacks the electrophilic carbon of the carbonyl group. - **Mechanism**: The nucleophilic CH₃⁻ from the Grignard reagent attacks the carbonyl carbon (C=O), leading to the formation of an alkoxide intermediate. The reaction can be represented as: \[ CH_3C(=O)CH_2CH_3 + CH_3MgBr \rightarrow CH_3C(OH)(CH_2CH_3)CH_3MgBr \] This intermediate is denoted as X: \[ X = CH_3C(OH)(CH_2CH_3)CH_3MgBr \] ### Step 2: Formation of Y Next, we treat X with dilute acid (H₃O⁺) to protonate the alkoxide and convert it into an alcohol. - **Reaction**: \[ CH_3C(OH)(CH_2CH_3)CH_3MgBr + H_3O^+ \rightarrow CH_3C(OH)(CH_2CH_3)CH_3 + MgBr^+ \] This gives us the alcohol Y: \[ Y = CH_3C(OH)(CH_2CH_3)CH_3 \] ### Step 3: Formation of Z Now, we treat Y with concentrated sulfuric acid (H₂SO₄) at 170°C. This will lead to dehydration, where water is eliminated to form an alkene. - **Mechanism**: The alcohol undergoes dehydration to form a carbocation, which can then rearrange or eliminate to form the double bond. The reaction can be represented as: \[ CH_3C(OH)(CH_2CH_3) \xrightarrow{H_2SO_4, 170°C} CH_3C^+(CH_2CH_3) + H_2O \] From the carbocation, two possible alkenes can form: 1. \( CH_3C(CH_2)CH_2 \) (1-butene) 2. \( CH_3C(CH_3)CH \) (2-butene) The more stable alkene will be the one with more alkyl substituents (more alpha hydrogens), which is 2-butene. Thus, the final product Z is: \[ Z = CH_3C(CH_3)=CH_2 \] (2-butene) ### Final Answer: Z is 2-butene. ---

To solve the given reaction sequence, we will break it down step by step, identifying the products at each stage. ### Step 1: Formation of X We start with the compound: \[ CH_3C(=O)CH_2CH_3 + CH_3MgBr \] This is a reaction between an aldehyde (or ketone) and a Grignard reagent (CH₃MgBr). The Grignard reagent acts as a nucleophile and attacks the electrophilic carbon of the carbonyl group. ...
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DISHA PUBLICATION-ALDEHYDES, KETONES AND CARBOXYLIC ACIDS-Exercise - 2 : Concept Applicator
  1. The product formed in the reaction is -

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  2. (A)underset("dil."H(2)SO(4))overset(HgSO(4))(to)(B)overset(LiAlH(4))(t...

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  3. overset(P C C)rarr (C )overset(HO^(-))underset(Delta)rarr (D ) What ...

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  4. Identify correct combination :

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  5. Which of the following is the product of aldol condensation?

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  6. Which of the following reagent(s) used for the conversion?

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  7. Which of the following reaction with (CH(3)CH(2))(2)NH to give the com...

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  8. CH(3)-overset(O)overset(||)C-CH(2)-CH(3)+CH(3)MgBrrarr X overset(H(3)O...

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  9. C(6)H(5)overset(O)overset(||)C CH(3)+C(6)H(5)CHO overset(H^(+))rarr C(...

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  10. The structure of the compound Y in the following reactions should be

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  11. Reaction of cyclohexanone with dimethylamine in the presence of cataly...

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  12. The increasing order of the rate of HCN addition to compound A-D is ...

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  13. Which of the following statement is incorrect about the reaction of am...

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  15. Product A is :

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  16. The compound (X) is

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  17. What is Z in the following sequence of reactions? Phenolunderset("du...

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  18. Which beta-keto acid shown will not undergo decarboxylation?

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  19. The reaction of sodium with acetyl chloride proceeds through which of ...

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  20. Calculate number of molecules of Grignard reagent consumed by 1 molecu...

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