Home
Class 12
CHEMISTRY
What is the product of the following rea...

What is the product of the following reactions?
`Me - overset(Me) overset(|)underset(Me ) underset(|) C-C=CHoverset({:((i)H_(2)SO_(4//HgSO_(4))), ((ii) NaBH_(4)):})underset({:((iii) Conc. H _(2) SO_(4)), ((iv) O _(3) ZnH_(2) O ):})to`

A

only `CH_(3) CH_(2) CHO`

B

only `CH _(3) - overset(O) overset(|) C - CH _(3)`

C

only `CH _(3) CHO`

D

only `CH _(3) CH_(2) COOH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the product of the given reactions, we will break down the process step by step. ### Step 1: Identify the Starting Compound The starting compound is a terminal alkyne, specifically 3-methyl-1-butyne, which can be represented as: \[ \text{Me}-\text{C}\equiv\text{C}-\text{Me} \] ### Step 2: Reaction with HgSO4 and H2SO4 The first reaction involves treating the alkyne with dilute sulfuric acid (H2SO4) and mercuric sulfate (HgSO4). This reaction leads to the formation of an enol through electrophilic addition: 1. The triple bond reacts with Hg^2+ to form a vinyl cation. 2. Water (from the dilute acid) attacks the vinyl cation, leading to the formation of an enol. The product after this step is: \[ \text{Me}-\text{C}(\text{OH})=\text{C}(\text{Me})-\text{H} \] ### Step 3: Tautomerization to Ketone The enol formed is not stable and undergoes tautomerization to form a ketone: \[ \text{Me}-\text{C}(\text{O})=\text{C}(\text{Me})-\text{Me} \] This product is 3-pentanone (or 3-methyl-2-butanone). ### Step 4: Reduction with NaBH4 Next, the ketone is reduced using sodium borohydride (NaBH4), which converts the ketone into an alcohol: \[ \text{Me}-\text{C}(\text{OH})-\text{C}(\text{Me})-\text{Me} \] This product is 3-pentanol. ### Step 5: Dehydration with Concentrated H2SO4 The alcohol undergoes dehydration when treated with concentrated sulfuric acid, leading to the formation of an alkene: 1. Protonation of the alcohol group occurs, forming a good leaving group. 2. Elimination of water leads to the formation of the alkene. The product after dehydration is: \[ \text{Me}-\text{C}=\text{C}(\text{Me})-\text{Me} \] This is 3-methyl-2-pentene. ### Step 6: Ozonolysis Finally, the alkene undergoes ozonolysis (O3 followed by Zn/H2O), which cleaves the double bond and forms two ketones: \[ \text{Me}-\text{C}(\text{O})-\text{C}(\text{Me})-\text{O} \] This results in the formation of two moles of acetone (CH3COCH3). ### Final Product The final product of the reactions is two moles of acetone. ### Summary of Steps 1. Start with terminal alkyne. 2. React with HgSO4 and H2SO4 to form an enol. 3. Tautomerize the enol to form a ketone. 4. Reduce the ketone with NaBH4 to form an alcohol. 5. Dehydrate the alcohol with concentrated H2SO4 to form an alkene. 6. Perform ozonolysis to yield two moles of acetone.

To solve the question regarding the product of the given reactions, we will break down the process step by step. ### Step 1: Identify the Starting Compound The starting compound is a terminal alkyne, specifically 3-methyl-1-butyne, which can be represented as: \[ \text{Me}-\text{C}\equiv\text{C}-\text{Me} \] ### Step 2: Reaction with HgSO4 and H2SO4 The first reaction involves treating the alkyne with dilute sulfuric acid (H2SO4) and mercuric sulfate (HgSO4). This reaction leads to the formation of an enol through electrophilic addition: ...
Promotional Banner

Topper's Solved these Questions

  • JEE Main Revision Test-9 | JEE-2020

    VMC MODULES ENGLISH|Exercise CHEMISTRY SECTION 2|5 Videos
  • LIQUID SOLUTION

    VMC MODULES ENGLISH|Exercise IMPECCABLE|100 Videos

Similar Questions

Explore conceptually related problems

What will be the product of the following reaction Ph-underset(Me)underset(|)(C)-Me overset(RCO_(3)H)to ?

What is the final product of the following reaction sequence? (CH_(3))_(3) C-C-=C-H overset((i)dil.H_(2)SO_(4)//HgSO_(4))underset({:(,(ii) NaBH_(4)//"ethanol"),(,"(iii) dil . acid"):})to

What is Z in the following sequence of reactions? Z overset(PCl_(3))toX overset(alc.KOH)to Y underset((ii)H_(2)O boil)overset((i)Conc.H_(2)SO_(4))toZ

Predict product of following reaction, H_(3)C-overset(O)overset(||)(C)-O-C_(2)H_(5)overset(NaBH_(4))to

End product of the following sequence is : CaO + C overset( "Heat")to (A) overset(H_(2)O)to(c) underset(H_(2)SO_(4))overset(Hg^(2+))to(C)

The major product (Y) in the following reactions is: CH_(3)-overset(CH_(3))overset(|)CH-C-=CH overset(HgSO_(4),H_(2)SO_(4))underset(H_(2)O)toX overset((i)C_(2)H_(5)MgBr,H_(2)O)underset((ii)"Conc",H_(2)SO_(4)//Delta)toY

CH_(3)underset(CH_(3))underset(|)(CH)-CH=CH_(2)underset((ii)H_(2)O_(2)//OH)overset((i)B_(2)H_(4))toXunderset(140^(@))overset(H_(2)SO_(4))toY What is Y ?

The product of following reaction is: underset(CHCl_(3))overset(H_(2)SO_(4)("Cat."))rarr

The major product of the following equation is. C_(2)H_(5)-overset(CH_(3))overset("| ")underset(Ph)underset("| ")"C "-CH_(2)-underset(OH)underset("| ")"CH"-CH_(3)overset("conc. "H_(2)SO_(4))underset(Delta)rarr

VMC MODULES ENGLISH-JEE MAIN REVISON TEST-23-CHEMISTRY (SECTION 1)
  1. Text Solution

    |

  2. A solution of Benzyl chloride, Benzoic acid and Aniline was extracted ...

    Text Solution

    |

  3. The number of orbitals associated with quantum numbers n =4 and m (8) ...

    Text Solution

    |

  4. Oxidation number of manganese in KMnO(4). MnO (2), K(2) MnO (4). respe...

    Text Solution

    |

  5. Consider the following reactions : (a) ( CH 3) 3 CCH ( O...

    Text Solution

    |

  6. Atomic radius of Ag is similar to

    Text Solution

    |

  7. In zeolites & synthetic resin method which will be more efficient...

    Text Solution

    |

  8. The impurest form of iron is:

    Text Solution

    |

  9. The dipole moments of CH(3)Cl , CH(2)Cl(2), CHCl(3) are in the order

    Text Solution

    |

  10. The electron gain enthalpy ( in kJ//mol ) of fluorine, chlorine,...

    Text Solution

    |

  11. What is the product of the following reactions? Me - overset(Me) ov...

    Text Solution

    |

  12. The relative strength of interionic / intermolecular forces in d...

    Text Solution

    |

  13. In the reaction : the product E is

    Text Solution

    |

  14. The increasing order of K (b) for the following compounds will be: H...

    Text Solution

    |

  15. Ligands are broadly classified into two classes classical and non-clas...

    Text Solution

    |

  16. The number of chiral carbons in Ibuprofen "."

    Text Solution

    |

  17. 1 mL of 0.1 N HCl is added to 999 mL solution of NaCl. The pH of the r...

    Text Solution

    |

  18. Strontium 90 is one of the harmful nuclides resulting from nuclear fis...

    Text Solution

    |

  19. For the reaction, 2A (s) + 2B (g)to C (g) + D(s) at 298K Delta U ^(@...

    Text Solution

    |

  20. Chlorine reacts with hot and conc. Ba (OH)(2) and produces compound X,...

    Text Solution

    |