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What is product of the following sequenc...

What is product of the following sequence of reactions ?
`(CH_(3))_(2)C=CHCH_(2)CH_(3)overset((i)BH_(3)//THF)underset((ii)H_(2)O_(2),OH^(-))rarr overset("PCC")underset(CH_(2)Cl_(2))rarr overset((i)CH_(3)MgBr)underset((ii)H_(3)O^(+))rarr`

A

2, 4 - dimethyl - 3- pentanol

B

2, 3 - dimethyl - 3- pentanol

C

2, 3 - dimethyl - 2- pentanol

D

2, 2 - dimethyl - 3 - pentanol

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The correct Answer is:
To determine the product of the given sequence of reactions, we will break down each step systematically. ### Step 1: Hydroboration-Oxidation The starting compound is `(CH₃)₂C=CHCH₂CH₃`, which is an alkene. We will first perform hydroboration using BH₃ in THF followed by oxidation with H₂O₂ and OH⁻. 1. **Hydroboration**: The alkene reacts with BH₃, leading to the formation of an organoborane intermediate. According to the anti-Markovnikov rule, the boron atom will attach to the less substituted carbon (the one with fewer hydrogens), and the hydrogen will add to the more substituted carbon. - The product of this step will be: `(CH₃)₂C(OH)CH₂CH₃` (an alcohol). 2. **Oxidation**: The organoborane intermediate is then oxidized with H₂O₂ in the presence of OH⁻, replacing the boron with a hydroxyl group. - The final product after this step is: `(CH₃)₂C(OH)CH₂CH₃`. ### Step 2: Oxidation with PCC The alcohol obtained from the previous step is now treated with PCC (Pyridinium Chlorochromate) in CH₂Cl₂, which is a mild oxidizing agent. 1. **Oxidation of Alcohol to Ketone**: The alcohol will be oxidized to a ketone by removing two hydrogen atoms and adding an oxygen atom. - The product after this step will be: `(CH₃)₂C=OCH₂CH₃` (a ketone). ### Step 3: Reaction with Grignard Reagent Next, we will react the ketone with a Grignard reagent, `CH₃MgBr`, followed by hydrolysis with `H₃O⁺`. 1. **Nucleophilic Attack**: The Grignard reagent acts as a nucleophile and attacks the electrophilic carbonyl carbon of the ketone. This forms a tetrahedral intermediate. - The intermediate will be: `CH₃C(OH)(CH₃)CH₂CH₃`. 2. **Hydrolysis**: The intermediate is then hydrolyzed with `H₃O⁺`, which will protonate the alkoxide to form the final alcohol. - The final product after hydrolysis will be: `CH₃C(OH)(CH₃)CH₂CH₃`. ### Final Product The final product of the entire reaction sequence is: **2,3-dimethyl-3-pentanol**. ### Summary of Steps 1. Hydroboration-Oxidation of alkene to form an alcohol. 2. Oxidation of the alcohol to a ketone using PCC. 3. Nucleophilic attack by Grignard reagent followed by hydrolysis to form the final alcohol.

To determine the product of the given sequence of reactions, we will break down each step systematically. ### Step 1: Hydroboration-Oxidation The starting compound is `(CH₃)₂C=CHCH₂CH₃`, which is an alkene. We will first perform hydroboration using BH₃ in THF followed by oxidation with H₂O₂ and OH⁻. 1. **Hydroboration**: The alkene reacts with BH₃, leading to the formation of an organoborane intermediate. According to the anti-Markovnikov rule, the boron atom will attach to the less substituted carbon (the one with fewer hydrogens), and the hydrogen will add to the more substituted carbon. - The product of this step will be: `(CH₃)₂C(OH)CH₂CH₃` (an alcohol). ...
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The final product of the following sequence of reaction is : (CH_(3)O)_(2)CHCH_(2)CH_(2)CH_(2)Broverset(Mg)(to) overset(H_(2)C=O)(to)underset("heat")overset(H_(3)O^(+))(to)

The product of the following reaction are CH_(3)C=C.CH_(2)CH_(3)=overset((i)O_(3))underset((ii)Hydrolysis)rarr?

What is the final product of the reaction? (CH_3)_(2) = CHCH_2CH_(3) overset((i) BH_3//THF)(rarr)overset(PCC)(rarr) underset((ii)H_2O^+)overset((i) CH_3MgBr)(rarr)

Complete the following reaction sequence : CH_(3)-overset(O)overset(||)C-CH_(3)overset((i)CH_(3)MgBr)underset((ii)H_(2)O)rarr(A)overset("Na metal")underset("ether")rarr(B)overset(CH_(3)-Br)rarr(C)

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

DISHA PUBLICATION-ALCOHOLS, PHENOLS AND ETHERS-Exercise - 2 : Concept Applicator)
  1. Which of the following alcohols on dehydration with conc. H(2)SO(4) wi...

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  2. Dehydration of alcohol by conc. H(2)SO(4) takes place according to fol...

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  3. Product is

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  4. During the dehydration of alcohols to alkenes by heating with conc. H(...

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  5. B(mix)overset(conc.HI)underset(2) larr (CH(3))(3)C-O-CH(3) overset("an...

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  6. ClCH2CH(2)OH is stronger acid than CH(3)CH(2)OH because of :

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  7. CH(3)-CH=CH(2)overset((i)Hg(OA c)(2)//H(2)O)underset((ii)NaBH(4))rarr ...

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  8. What is product of the following sequence of reactions ? (CH(3))(2)C...

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  9. Identify the nature of product in the following reaction

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  10. Which electrophile is likely to be formed as an intermediate in the fo...

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  11. Phenol is

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  12. What is the structure of the major product when phenol is treated with...

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  13. The structure of the compound that gives a tribromo derivative on trea...

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  14. "Phenol "overset(NaNO(2)//H(2)SO(4))rarr B overset(H(2)O)rarr C overse...

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  15. The major product P in the following reaction is (CH(3))(3)COH+C(2)H...

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  16. An ether, (A) having molecular formula, C(6)H(14)O, when treated with ...

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  17. HBr reacts with H(2)C=CH-OCH(3) under anhydrous conditions at room tem...

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  18. CH(3)underset(CH(3))underset(|)(CH)-CH=CH(2)underset((ii)H(2)O(2)//OH)...

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  19. The reaction can be classified as:-

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  20. Which one is the most acidic compound?

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