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In the following sequence of reactions, ...

In the following sequence of reactions, the compound C formed would be
`CH_(3)-underset(NH_(2))underset("| ")"CH"-CH_(3)overset(HNO_(2))underset(H_(2)O)rarr A overset([O])rarr B overset(CH_(3)MgI)underset(H^(+)//H_(2)O)rarr C`

A

1, 1 - Dimethylethanol

B

Butanol - 1

C

Butanol - 2

D

2 - Methyl - propanol - 1

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given sequence of reactions step by step, let's break it down: ### Step 1: Reaction with HNO2 and H2O The starting compound is CH3-CH(NH2)-CH3 (isopropylamine). When isopropylamine reacts with nitrous acid (HNO2) in the presence of water, it undergoes a reaction where the amino group (-NH2) is converted to a hydroxyl group (-OH) through the formation of a diazonium ion (N2+), which is a good leaving group. The reaction can be summarized as follows: \[ \text{CH}_3\text{-CH(NH}_2)\text{-CH}_3 + \text{HNO}_2 + \text{H}_2\text{O} \rightarrow \text{CH}_3\text{-CH(OH)-CH}_3 + \text{N}_2 + \text{H}_2\text{O} \] The product formed here is **A**, which is **CH3-CH(OH)-CH3** (isopropanol). ### Step 2: Oxidation of Alcohol to Ketone Next, we oxidize the alcohol (isopropanol) to a ketone. The oxidation can be achieved using an oxidizing agent, which we denote as [O]. The reaction can be represented as: \[ \text{CH}_3\text{-CH(OH)-CH}_3 \overset{[O]}{\rightarrow} \text{CH}_3\text{-C(=O)-CH}_3 \] The product formed here is **B**, which is **CH3-CO-CH3** (acetone). ### Step 3: Reaction with Grignard Reagent Now we react the ketone (acetone) with a Grignard reagent, which is CH3MgI. The Grignard reagent will attack the carbonyl carbon of the ketone, leading to the formation of a tertiary alcohol. The reaction can be summarized as follows: 1. The nucleophilic carbon from the Grignard reagent attacks the carbonyl carbon: \[ \text{CH}_3\text{-C(=O)-CH}_3 + \text{CH}_3\text{MgI} \rightarrow \text{CH}_3\text{-C(OH)(CH}_3)\text{-CH}_3 \] 2. After the addition of water (H+ and H2O), the alkoxide ion (O-) formed will pick up a proton (H+): \[ \text{CH}_3\text{-C(OH)(CH}_3)\text{-CH}_3 + \text{H}_2\text{O} \rightarrow \text{CH}_3\text{-C(OH)(CH}_3)\text{-CH}_3 \] The final product **C** is **CH3-C(OH)(CH3)-CH3**, which is **2-propanol** or **tert-butyl alcohol**. ### Final Answer The compound C formed would be **2-propanol (tert-butyl alcohol)**. ---

To solve the given sequence of reactions step by step, let's break it down: ### Step 1: Reaction with HNO2 and H2O The starting compound is CH3-CH(NH2)-CH3 (isopropylamine). When isopropylamine reacts with nitrous acid (HNO2) in the presence of water, it undergoes a reaction where the amino group (-NH2) is converted to a hydroxyl group (-OH) through the formation of a diazonium ion (N2+), which is a good leaving group. The reaction can be summarized as follows: \[ \text{CH}_3\text{-CH(NH}_2)\text{-CH}_3 + \text{HNO}_2 + \text{H}_2\text{O} \rightarrow \text{CH}_3\text{-CH(OH)-CH}_3 + \text{N}_2 + \text{H}_2\text{O} \] The product formed here is **A**, which is **CH3-CH(OH)-CH3** (isopropanol). ...
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DISHA PUBLICATION-AMINES-Exercise - 1 : Concept Builder (Topicwise)(TOPIC - 1 : Amines and Amides)
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  4. The indicator that is obtained by coupling the diazonium salt of sulph...

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  5. In a reaction of aniline a coloured product C was obtained. The s...

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  6. The alkene formed as a major product in the above elimination reaction...

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  7. Predict about the relative boiling point of the following two amines.

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  8. Identify Z in the following sequence of reactions - CH(3)COONH(4) ov...

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  9. Which of the following will produce isopropyl amine - (I) (CH(3))(2...

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  10. In the following sequence of reactions, the compound C formed would be...

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  11. Among the following isomeric C(4)H(11)N amines, one having the lowest ...

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  12. Which of the following does not give N - ethyl cyclopentylamine as maj...

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  13. Which of the following compounds is an enamine?

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  14. Which of the following reaction will not given N, N - dimethyl benzami...

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  15. A compound 'Z' reacts with three moles of CH(3)I and gives a product w...

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  16. The cyclobutyl methylamine with nitrous acid gives

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  17. The correct order of decreasing basic character of the three aliphatic...

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  18. Predict the possible number of alkenes and the main alkene in the foll...

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  20. Which of the following reactions is appropriate for converting acetami...

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