Home
Class 12
CHEMISTRY
C(2)H(5)O-overset(O)overset(||)(C )-OC(2...

`C_(2)H_(5)O-overset(O)overset(||)(C )-OC_(2)H_(5) overset(2MeMgBr)(rarr) (A)`. The product `(A)` formed can:

A

a.give iodoform test.

B

b.further react with `MeMgBr//H_(3)O^(o+)` to give t-butyl alcohol.

C

c.be obtained by the ozonolysis of 2, 3-dimethyl 1-2-butene.

D

d.all correct

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given problem, we will analyze the reaction step by step, focusing on the interaction between the reactants and the Grignard reagent. ### Step-by-Step Solution 1. **Identify the Reactants**: The starting compound is an ether with the structure C2H5O-C(=O)-C2H5, which contains a carbonyl group (C=O) and two ethyl groups (C2H5). 2. **Reaction with Grignard Reagent**: The compound reacts with two moles of methyl magnesium bromide (MeMgBr). The carbonyl group is electrophilic and will react with the nucleophilic methyl group from the Grignard reagent. 3. **First Reaction Step**: - The methyl group (CH3-) from the first mole of MeMgBr attacks the carbonyl carbon (C=O), forming an alkoxide intermediate. - The oxygen atom in the carbonyl group becomes negatively charged, while the carbon becomes positively charged. - The reaction can be represented as: \[ C2H5O-C(=O)-C2H5 + CH3MgBr \rightarrow C2H5O-C(-O^{-}CH3)-C2H5 \] 4. **Formation of the Intermediate**: The intermediate formed after the first reaction is a tetrahedral alkoxide. The negatively charged oxygen will now have a bond with the methyl group. 5. **Leaving Group**: The alkoxide intermediate can then collapse, leading to the elimination of the ethoxy group (C2H5O-) as a good leaving group. This results in the formation of a ketone: \[ C2H5O-C(-O)-C2H5 \rightarrow C2H5-C(=O)-CH3 + C2H5O^{-} \] This ketone is acetone (CH3COC2H5). 6. **Second Reaction Step**: The second mole of MeMgBr will now attack the carbonyl carbon of the formed acetone: \[ CH3COC2H5 + CH3MgBr \rightarrow CH3C(OH)(C2H5)CH3 \] This results in the formation of a tertiary alcohol after hydrolysis. 7. **Final Product**: The final product after hydrolysis is a tertiary butyl alcohol (tert-butanol). 8. **Tests for Product A**: The product formed, acetone, can undergo the iodoform test, which is characteristic of methyl ketones. Additionally, ozonolysis of 2,3-dimethylbutene can yield acetone. ### Conclusion The final product (A) formed from the reaction can give the iodoform test and can also be prepared from the ozonolysis of 2,3-dimethylbutene.

To solve the given problem, we will analyze the reaction step by step, focusing on the interaction between the reactants and the Grignard reagent. ### Step-by-Step Solution 1. **Identify the Reactants**: The starting compound is an ether with the structure C2H5O-C(=O)-C2H5, which contains a carbonyl group (C=O) and two ethyl groups (C2H5). 2. **Reaction with Grignard Reagent**: The compound reacts with two moles of methyl magnesium bromide (MeMgBr). The carbonyl group is electrophilic and will react with the nucleophilic methyl group from the Grignard reagent. ...
Promotional Banner

Topper's Solved these Questions

  • REDUCTION AND OXIDATION REACTION OF ORGANIC COMPOUNDS

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercise (Assertion And Reasoning)|10 Videos
  • REDUCTION AND OXIDATION REACTION OF ORGANIC COMPOUNDS

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercise Archives (Subjective)|26 Videos
  • REDUCTION AND OXIDATION REACTION OF ORGANIC COMPOUNDS

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercise (Multiple Correct)|35 Videos
  • QUALITATIVE INORGANIC SALT ANALYSIS

    CENGAGE CHEMISTRY ENGLISH|Exercise Viva Voce Questions And Part-C (Analysis Of Cations)|42 Videos
  • SOLID STATE

    CENGAGE CHEMISTRY ENGLISH|Exercise Ex 1.2 (Objective)|9 Videos

Similar Questions

Explore conceptually related problems

In the given reaction CH_(2)-CH_(2)-overset(O)overset(||)C-CH_(2)COOC_(2)H_(5)overset([X])rarr (A) overset((i)LiAlH_(4))underset((ii)H_(2)O //H^(o+))rarr CH_(3)-CH_(2)-overset(O)overset(||)C-CH_(2)-CH_(2)OH+C_(2)H_(5)OH [X] will be

Ester having alpha -hydrogen on treatement with a strong base eg. C_(2)H_(5)Ona undergoes self condensation to produce beta -keto esters. This is called claisen condensation EtO-overset(O)overset(||)(C)-OEt+Ph-CH_(2)-overset(O)overset(||)(C)-OC_(2)H_(5) overset((1)C_(2)H_(5)ONa)underset((2)H_(2)O,Delta)to products is

Find the last product [D] in reaction sequence C_(6)H_(5)CHO+CH_(3)-overset(O)overset(||)C-CH_(2)-COOC_(2)H_(5) overset(H_3O^(+))to A overset(Delta)to C underset(OH^(-)//Delta) overset(NH_2-NH_2)to D

Write the structures of products (A) and (B) CH_(3) -overset (O) overset(||) C-overset(18) OC_2 H_5 overset(H_(3) O^(+))rarr (A) + (B) .

Ester having alpha -hydrogen on treatement with a strong base eg. C_(2)H_(5)Ona undergoes self condensation to produce beta -keto esters. This is called claisen condensation C_(6)H_(5)-underset(O)underset(||)(C)-OC_(2)H_(5)+CH_(3)-underset(O)underset(||)(C)-OC_(2)H_(5) overset((1) C_(2)H_(5)overset(Theta)(O)Na^(o+))underset((2) H^(o+))to

CH_(3)CH_(2)-overset(O)overset(||)C-O-C_(2)H_(2)overset((i)DIBAL.H(1 eq))underset((ii)H_(3)O^(+)) to A+B A and B are respectively.

CENGAGE CHEMISTRY ENGLISH-REDUCTION AND OXIDATION REACTION OF ORGANIC COMPOUNDS-Exercise (Single Correct)
  1. C(6)H(10)O(3) (Keto ester)(A)underset(Delta)overset(NaOH+I(2))(rarr) Y...

    Text Solution

    |

  2. Suggest a suitable oxidising reagent for the following conversions:

    Text Solution

    |

  3. C(2)H(5)O-overset(O)overset(||)(C )-OC(2)H(5) overset(2MeMgBr)(rarr) (...

    Text Solution

    |

  4. Which of the following compounds will not give haloform reaction?

    Text Solution

    |

  5. Identify the set from the following which connot form acetone in a sin...

    Text Solution

    |

  6. (A) will not

    Text Solution

    |

  7. CH(3)CH(2)NO(2) underset(at 0^(@)C)overset(NaNO(2)+HBr)(rarr) (A). (A)...

    Text Solution

    |

  8. Which of the following does not give Liebermann's nitroso reaction?

    Text Solution

    |

  9. Of the following compounds, whose ozonolysis proves the Kekule structu...

    Text Solution

    |

  10. CH(3)-overset(CH(3))overset(|)(CH)-NO(2) underset(at 0^(@)C)overset(Na...

    Text Solution

    |

  11. Which of the following compounds are (A), (B), (C ), and (D)? Ph-ove...

    Text Solution

    |

  12. The compound (A)

    Text Solution

    |

  13. Fenton's regent (Fe^(2+)+H(2)O(2)) with benzene gives:

    Text Solution

    |

  14. Lactic acid on oxidation with Fenton's reagent gives:

    Text Solution

    |

  15. The compounds (A) and (B) are:

    Text Solution

    |

  16. (A) is:

    Text Solution

    |

  17. The compound (A) is:

    Text Solution

    |

  18. The compound (A) is:

    Text Solution

    |

  19. Which single reagent can be used in the following conversions?

    Text Solution

    |

  20. Et-N^(o+)-=C^(ɵ) underset(or HgO or O(3))overset(Cl(2)+DMSO)(rarr). Th...

    Text Solution

    |