Home
Class 12
CHEMISTRY
CH(3)CH(2)CH(OH)CH(CH(3))(2)+CH(3)COCI o...

`CH_(3)CH_(2)CH(OH)CH(CH_(3))_(2)+CH_(3)COCI overset("base")rarr CH_(3)CH_(2)CH(OCOCH_(3))CH(CH_(3))_(2)+HCI` In the above reaction, if the reactant alcohol is a pure R-isomer the product would.

A

Have configuration inverted at the chiral atom

B

be a racemic mixture

C

have the same configuration at the chiral atom

D

be optically inactive

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reaction step by step, focusing on the stereochemistry involved when the reactant alcohol is a pure R-isomer. ### Step-by-Step Solution: 1. **Identify the Reactant Structure:** The reactant is an alcohol with the structure CH3CH2CH(OH)CH(CH3)2. The hydroxyl (OH) group is attached to the third carbon, which makes this carbon a chiral center because it is bonded to four different groups: - CH3 (methyl group) - CH2CH3 (ethyl group) - OH (hydroxyl group) - H (hydrogen atom) 2. **Determine the Configuration of the Chiral Center:** Since the reactant is specified as a pure R-isomer, we can assign the configuration at the chiral center. The priority of the substituents is determined by atomic number: - OH has the highest priority (1) - CH3 (methyl) is second (2) - CH2CH3 (ethyl) is third (3) - H (hydrogen) is lowest (4) When arranged in order of priority, if you trace a path from 1 to 2 to 3, it goes in a clockwise direction, confirming that it is indeed an R configuration. 3. **Reaction with Acetyl Chloride:** The alcohol reacts with acetyl chloride (CH3COCl) in the presence of a base. The base helps in the nucleophilic attack of the hydroxyl oxygen on the carbonyl carbon of acetyl chloride, leading to the formation of an intermediate. 4. **Formation of the Product:** The product formed will have the structure CH3CH2CH(OCOCH3)CH(CH3)2. The carbon that was originally the chiral center now has a new substituent (OCOCH3) replacing the OH group. 5. **Analyze the New Chiral Center:** The new chiral center still has four different groups: - OCOCH3 (acetyl group) - CH2CH3 (ethyl group) - CH(CH3)2 (isopropyl group) - H (hydrogen atom) The configuration at this new chiral center needs to be determined. The reaction mechanism involves the inversion of configuration at the chiral center due to the nucleophilic attack. 6. **Conclusion on Stereochemistry:** Since the reaction involves the inversion of configuration at the chiral center, the product will have the opposite configuration compared to the reactant. Therefore, if the reactant is a pure R-isomer, the product will be an S-isomer. ### Final Answer: If the reactant alcohol is a pure R-isomer, the product would have the configuration inverted at the chiral carbon atom, resulting in an S-isomer.
Promotional Banner

Topper's Solved these Questions

  • CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID

    RESONANCE ENGLISH|Exercise Part -III|31 Videos
  • CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID

    RESONANCE ENGLISH|Exercise Part -IV|23 Videos
  • CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID

    RESONANCE ENGLISH|Exercise APSP|1 Videos
  • BIOMOLECULES & POLYMER

    RESONANCE ENGLISH|Exercise ORGANIC CHEMISTRY(Biomolecules & Polymer)|34 Videos
  • CHEMICAL KINETICS

    RESONANCE ENGLISH|Exercise PHYSICAL CHEMITRY (CHEMICAL KNIETICS & RADIOACTIVITY)|49 Videos

Similar Questions

Explore conceptually related problems

CH_(2)OHCH_(2)CH_(2)COCH_(3)overset("Reagent")rarr CH_(2)OHCH_(2)CH_(2)CH_(2)CH_(3) Suitable reagent for above reaction is :-

CH_(3)CH_(2)CH(CHO)CH_(2)CH_(3) and CH_(3)CH(CHO) CH_(2)CH_(2)CH_(3) are :-

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

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

CH_(3)""^(.)CH_(2)CH_(2)Cl overset(aq. KOH)(to) CH_(3)CH_(2)CH_(2)OH The reaction is

CH_(3)-CH_(2)-O-CH_(2)-CH_(3)+O_(2)overset(hv)rarr (A) The product (A) is:

RESONANCE ENGLISH-CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID -Part -II
  1. Compound "X" in the following reaction is

    Text Solution

    |

  2. Compound "X" in the following reaction is

    Text Solution

    |

  3. Compound 'P' that undergoes the sequence of reactions given below to g...

    Text Solution

    |

  4. The major product of the following reaction is

    Text Solution

    |

  5. The reaction , RCH(2)CH(2)COOH overset("Red P") underset(Br(2)) to R ...

    Text Solution

    |

  6. Formic acid and acetic acid can be distinguished with

    Text Solution

    |

  7. One of the product formed in the electrolysis of sodium salt of succin...

    Text Solution

    |

  8. The compound that gives a lactone on heating is

    Text Solution

    |

  9. The compound that undergoes decarboxylation most readily under mild co...

    Text Solution

    |

  10. The most unstable compounds fo the following are :

    Text Solution

    |

  11. The product obtained when propanamide is distilled with phosphorous pe...

    Text Solution

    |

  12. The product B of the following sequence of reactions is C(6)H(5)CONH...

    Text Solution

    |

  13. What is the major product obtained from the following reactions ? HO...

    Text Solution

    |

  14. What is the major product obtained from the following reactions ? CH...

    Text Solution

    |

  15. The compound X(C(7)H(9)N) reacts with benzensulfonyl chloride to give ...

    Text Solution

    |

  16. CH(3)CH(2)CH(OH)CH(CH(3))(2)+CH(3)COCI overset("base")rarr CH(3)CH(2)C...

    Text Solution

    |

  17. Give the structure of the compound ;3-methylbutanoic acid

    Text Solution

    |

  18. The major product (Y) of the following reactions is

    Text Solution

    |

  19. Give the structure of 4-amino-3-methylbutanoic acid

    Text Solution

    |

  20. The compound 'X' undergoing the following reaction is

    Text Solution

    |