Home
Class 12
CHEMISTRY
In the reaction: CH(3)-overset(CH(3))o...

In the reaction:
`CH_(3)-overset(CH_(3))overset(|)(C)H-CH_(2)-O-CH_(2)-CH_(3)+HI`
Which of the following compounds will be formed?

A

`CH_(3)-overset(CH_(3))overset(|)(C)H-CH_(2)OH+CH_(3)CH_(2)-I`

B

`CH_(3)-overset(CH_(3))overset(|)(C)H-CH_(2)I+CH_(3)CH_(2)OH`

C

`CH_(3)-underset(CH_(3))underset(|)(C)H-CH_(3)+CH_(3)CH_(2)OH`

D

`CH_(3)-underset(CH_(3))underset(|)(C)H-CH_(2)OH+CH_(3)CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reaction of the given ether with hydroiodic acid (HI). The ether in question is: \[ CH_3 - C(CH_3)(CH_2) - O - CH_2 - CH_3 \] ### Step 1: Identify the Ether The structure given is an ether, which consists of an alkoxy group (–O–) connecting two alkyl groups. In this case, we have a branched ether. **Hint:** Recognize the structure of ethers and how they are formed from alcohols. ### Step 2: Protonation of Ether When an ether reacts with a strong acid like HI, the first step is the protonation of the ether oxygen. This forms an oxonium ion: \[ CH_3 - C(CH_3)(CH_2) - O^+H - CH_2 - CH_3 \] **Hint:** Remember that protonation increases the electrophilicity of the ether, making it more reactive. ### Step 3: Cleavage of the Ether The oxonium ion can undergo cleavage. The bond between the oxygen and the carbon atoms can break. The cleavage will occur preferentially at the less sterically hindered carbon atom. In this case, we have two possible cleavage sites: 1. The bond between the oxygen and the ethyl group (–O–CH₂–CH₃). 2. The bond between the oxygen and the branched carbon (–O–C(CH₃)–). Due to steric hindrance, the bond to the ethyl group will break preferentially. **Hint:** Consider steric effects when determining which bond will break in ether cleavage. ### Step 4: Formation of Products Upon cleavage, we will form ethyl iodide (from the ethyl group) and isobutanol (from the branched carbon): 1. Ethyl iodide: \( CH_3 - CH_2 - I \) 2. Isobutanol: \( CH_3 - C(CH_3)(CH_2) - OH \) The final products are: \[ CH_3 - CH_2 - I + CH_3 - C(CH_3)(CH_2) - OH \] **Hint:** Write down the structures of the products to visualize the reaction outcome. ### Conclusion The compounds formed from the reaction of the given ether with HI are ethyl iodide and isobutanol. ### Final Answer The products formed are: 1. Ethyl iodide: \( CH_3 - CH_2 - I \) 2. Isobutanol: \( CH_3 - C(CH_3)(CH_2) - OH \) ### Summary of Steps 1. Identify the ether structure. 2. Protonate the ether with HI. 3. Determine the site of cleavage based on sterics. 4. Write down the resulting products.

To solve the problem, we need to analyze the reaction of the given ether with hydroiodic acid (HI). The ether in question is: \[ CH_3 - C(CH_3)(CH_2) - O - CH_2 - CH_3 \] ### Step 1: Identify the Ether The structure given is an ether, which consists of an alkoxy group (–O–) connecting two alkyl groups. In this case, we have a branched ether. **Hint:** Recognize the structure of ethers and how they are formed from alcohols. ...
Promotional Banner

Topper's Solved these Questions

  • ALCOHOLS, PHENOLS AND ETHERS

    PRADEEP|Exercise COMPETITION FOCUS JEE (MAIN AND ADVANCED)/MEDICAL ENTRANCES SPECIAL (MULTIPLE CHOICE QUESTIONS WITH ONE CORRECT ANSWER-II)|12 Videos
  • ALCOHOLS, PHENOLS AND ETHERS

    PRADEEP|Exercise COMPETITION FOCUS JEE (MAIN AND ADVANCED)/MEDICAL ENTRANCES SPECIAL (MULTIPLE CHOICE QUESTIONS -III) Comprehension|8 Videos
  • ALCOHOLS, PHENOLS AND ETHERS

    PRADEEP|Exercise VALUE BASED QUESTIONS WITH ANSWERS|4 Videos
  • ALDEHYDES, KETONES AND CARBOXYLIC ACIDS

    PRADEEP|Exercise IMPORTANT QUESTIONS FOR BOARD EXAMINATION|29 Videos

Similar Questions

Explore conceptually related problems

In the reaction CH_(3)overset(CH_(3))overset(|)(C )H-CH_(2)-O-CH_(2)CH_(3)+Hioverset(Heated)(rarr) Which of the following compounds will be formed?

C_(6)H_(5)-O-CH_(2)CH_(3)overset(HI)rarr which of the following is not formed in this reaction ?

CH_(3)-CH_(2)-CH_(2)-O-CH_(3) and CH_(3)-overset(CH_(3))overset(|)(C )H-O-CH_(3) are

In the following hydration CH_(3)-overset(CH_(3))overset(|)(CH)-CH = CH_(2) overset(H_(3)O^(+))rarr the major product formed is

CH_(3)-overset(O)overset(||)(C)-O-CH_(2)-CH_(3)+H-O/^(-)rarr (O/=O^(18)) One of the product of the reaction is:

CH_(3)-overset(CH_(2)CH_(3))overset(|)(CH)CH=CHCH_(3)overset(H_(3)O^(+))rarr Major product of the reaction

PRADEEP-ALCOHOLS, PHENOLS AND ETHERS-COMPETITION FOCUS JEE (MAIN AND ADVANCED)/MEDICAL ENTRANCES SPECIAL (MULTIPLE CHOICE QUESTIONS WITH ONE CORRECT ANSWER-I)
  1. In Williamson's synthesis, ethoxyethane is pprepared by

    Text Solution

    |

  2. The reaction, is an example of

    Text Solution

    |

  3. Complete the following reaction

    Text Solution

    |

  4. The major product in the following reaction is

    Text Solution

    |

  5. Identify Z in the sequence of reactions: CH(3)CH(2)CH=CH(2)overset(H...

    Text Solution

    |

  6. Among the following sets of reactants which one produces anisole?

    Text Solution

    |

  7. Decreasing order of reactivity in Williamson's ether synthesis of the ...

    Text Solution

    |

  8. Among the following, one which reacts most readily with ethanol is

    Text Solution

    |

  9. Which of the following cannot be made by using Williamson's synthesis?

    Text Solution

    |

  10. Condiser the reactions, (i) (CH(3))(2)CH-CH(2)Broverset(C(2)H(5)OH)r...

    Text Solution

    |

  11. The acidic hydrolysis of ether (X) shown below is fastest when

    Text Solution

    |

  12. When H(2)C=CH-O-CH(2)CH(3) reacts with one molre of HI, one of the pr...

    Text Solution

    |

  13. tert-Butyl methyl ether on heating with HI gives a mixture of

    Text Solution

    |

  14. In the following reaction C(2)H(5)OC(2)H(5)+4Hoverset(Red P+HI)(rarr...

    Text Solution

    |

  15. In the reaction: CH(3)-overset(CH(3))overset(|)(C)H-CH(2)-O-CH(2)-CH...

    Text Solution

    |

  16. In the reaction the products are

    Text Solution

    |

  17. What are the products of the following reactions ? C(6)H(5)OCH(2)CH(...

    Text Solution

    |

  18. Which of the following compounds is resistant to nucleophilic attack b...

    Text Solution

    |

  19. A is

    Text Solution

    |

  20. Anisol overset((CH(3))(3)C Cl)underset(AlCl(3))(rarr)overset(Cl(2)//Fe...

    Text Solution

    |