Home
Class 11
CHEMISTRY
PhSO2CH2-CH2-OMeunderset(EtOD) overset(E...

`PhSO_2CH_2-CH_2-OMeunderset(EtOD) overset(EtO^(theta))to"product"+underset("(recovered reactant)")(PhSO_2-oversetoverset(D)(|)CH-CH_2OMe`.
The product is :

A

`PhSO_2CH=CH_2`

B

`CH_2=CH-O Me`

C

`PhSO_2CH_2-CD_2OMe`

D

`CD_2=CH_2`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reaction of the compound PhSO₂CH₂CH₂OMe with EtO⁻ in the presence of EtOD. Let's break down the reaction step by step. ### Step 1: Identify the Structure The starting compound can be represented as PhSO₂-CH₂-CH₂-OMe. Here, Ph represents a phenyl group (C₆H₅), SO₂ is a sulfonyl group, and OMe is a methoxy group (–OCH₃). ### Step 2: Deprotonation The base EtO⁻ (ethoxide ion) will act to deprotonate the most acidic hydrogen in the molecule. In this case, the hydrogen on the CH₂ adjacent to the sulfonyl group (PhSO₂) is the most acidic due to the electron-withdrawing effect of the sulfonyl group. The reaction can be represented as: \[ \text{PhSO}_2\text{-CH}_2\text{-CH}_2\text{-OMe} + \text{EtO}^- \rightarrow \text{PhSO}_2\text{-C}^- \text{H}\text{-CH}_2\text{-OMe} + \text{EtOH} \] ### Step 3: Formation of the Carbanion After deprotonation, we form a carbanion at the carbon adjacent to the sulfonyl group: \[ \text{PhSO}_2\text{-C}^- \text{H}\text{-CH}_2\text{-OMe} \] ### Step 4: Resonance Stabilization The carbanion formed is resonance-stabilized by the sulfonyl group. This stabilization allows the negative charge to delocalize, making the carbanion more stable. ### Step 5: Elimination Reaction The next step involves the elimination of the methoxy group (–OMe) as a leaving group. The carbanion can form a double bond with the adjacent carbon, leading to the formation of an alkene. The reaction can be represented as: \[ \text{PhSO}_2\text{-C}^- \text{H}\text{-CH}_2\text{-OMe} \rightarrow \text{PhSO}_2\text{-C}=\text{CH}_2 + \text{OMe}^- \] ### Step 6: Final Product The final product will be: \[ \text{PhSO}_2\text{-C}=\text{CH}_2 \] This product is a vinyl sulfone where the sulfonyl group is attached to a double-bonded carbon. ### Summary of the Reaction The overall reaction can be summarized as: \[ \text{PhSO}_2\text{-CH}_2\text{-CH}_2\text{-OMe} + \text{EtO}^- \rightarrow \text{PhSO}_2\text{-C}=\text{CH}_2 + \text{OMe}^- + \text{EtOH} \]

To solve the problem, we need to analyze the reaction of the compound PhSO₂CH₂CH₂OMe with EtO⁻ in the presence of EtOD. Let's break down the reaction step by step. ### Step 1: Identify the Structure The starting compound can be represented as PhSO₂-CH₂-CH₂-OMe. Here, Ph represents a phenyl group (C₆H₅), SO₂ is a sulfonyl group, and OMe is a methoxy group (–OCH₃). ### Step 2: Deprotonation The base EtO⁻ (ethoxide ion) will act to deprotonate the most acidic hydrogen in the molecule. In this case, the hydrogen on the CH₂ adjacent to the sulfonyl group (PhSO₂) is the most acidic due to the electron-withdrawing effect of the sulfonyl group. ...
Promotional Banner

Topper's Solved these Questions

  • ORGANIC REACTION MECHANISMS-IV

    RESONANCE ENGLISH|Exercise APSP PART-2|17 Videos
  • ORGANIC REACTION MECHANISMS-IV

    RESONANCE ENGLISH|Exercise APSP PART-3|22 Videos
  • ORGANIC REACTION MECHANISMS-IV

    RESONANCE ENGLISH|Exercise Exercise-3 Part-2 JEE (MAIN ) ONLINE PROBLEMS|10 Videos
  • ORGANIC REACTION MECHANISMS - II

    RESONANCE ENGLISH|Exercise APSP Part - 3|22 Videos
  • PERIODIC TABLE & PERIODICITY

    RESONANCE ENGLISH|Exercise ORGANIC CHEMISTRY(BASIC CONCEPTS)|27 Videos

Similar Questions

Explore conceptually related problems

2CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-CHO+NaOHrarr The product is

CH_(3)CH_(2)-underset(CH_(3))underset(|)(CH)-CH_(2)-O-CH_(2)CH_(3)+HIto ? The product is

CH_(3)underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH=CH_(2)overset(overset(+)(H)|H_(2)o)(to)'P' (major) product 'P' is-

The product of the given reaction , CH_3 - underset( OH )underset( |) overset(| ) overset( CH_3 ) overset(|) C-underset(NH_2 ) underset(|) overset(CH_(3) ) overset( |) C -CH_(3) overset( HNO_2 ) to Product is :

2CH_(3)-underset(O)underset(||)(C)-CH_(3) underset(H^(+))overset(Mg//Hg)to Product in the reaction is

CH_3-undersetunderset(CH_3)(|)CH-oversetoverset(Cl)(|)CH-CH_3 underset(Delta)overset(t-BuO) to Major Product is :

RESONANCE ENGLISH-ORGANIC REACTION MECHANISMS-IV-APSP PART-1
  1. The most probable product in the following reaction is :

    Text Solution

    |

  2. Complete the following reaction

    Text Solution

    |

  3. Which statement is false for elimination reaction .

    Text Solution

    |

  4. Which of the following statement is correct regarding following reacti...

    Text Solution

    |

  5. Substrate that show E1 reaction

    Text Solution

    |

  6. Which of the following compound will give three alkenes after dehydroh...

    Text Solution

    |

  7. PhSO2CH2-CH2-OMeunderset(EtOD) overset(EtO^(theta))to"product"+underse...

    Text Solution

    |

  8. Complete the following reaction

    Text Solution

    |

  9. Typical features of E2 involve :

    Text Solution

    |

  10. An alkyl chloride produces a single alkene on reaction with sodium eth...

    Text Solution

    |

  11. The relative ease of dehydration of alcohols follows following order :

    Text Solution

    |

  12. Which of the following is the correct major product for given reaction...

    Text Solution

    |

  13. Which of the following is a beta-elimination reaction ?

    Text Solution

    |

  14. Correct order of E2//SN2 ratio is :

    Text Solution

    |

  15. The product C of the following sequence is :

    Text Solution

    |

  16. The major product of the following reaction is

    Text Solution

    |

  17. What is the correct sequence of reagents for the following conversion ...

    Text Solution

    |

  18. In which of the following reaction the single product formed is not th...

    Text Solution

    |

  19. In the following reaction the correct order of percentage of products ...

    Text Solution

    |

  20. The rate of elimination is fastest in

    Text Solution

    |