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NEET CHEMISTRYHard

When glycerol is treated with an excess of HI, it produces:

A

Allyl iodide

B

Propene

C

Glycerol triiodide

D

2-Iodopropane

Step-by-Step Solution

The reaction of glycerol (propane-1,2,3-triol) with excess hydrogen iodide (HI) proceeds in several steps:

  1. Substitution: Initially, the three hydroxyl groups are replaced by iodine to form 1,2,3-triiodopropane.
  2. Elimination of Iodine: Vicinal diiodides are unstable due to the large size of iodine atoms. 1,2,3-triiodopropane loses a molecule of iodine (I2I_2) to form allyl iodide (CH2=CHCH2ICH_2=CH-CH_2I).
  3. Addition of HI: Allyl iodide reacts with another molecule of HI. The addition follows Markovnikov's rule, but the resulting product is 1,2-diiodopropane (CH3CHICH2ICH_3-CHI-CH_2I).
  4. Elimination of Iodine: 1,2-diiodopropane is also a vicinal diiodide and unstable; it loses I2I_2 to form propene (CH3CH=CH2CH_3-CH=CH_2).
  5. Final Addition: Propene reacts with the excess HI. According to Markovnikov's rule, the negative part (II^-) attaches to the carbon with fewer hydrogen atoms (the secondary carbon), yielding the stable final product 2-iodopropane (CH3CHICH3CH_3-CHI-CH_3).

(See NCERT Class 12, Unit 10 for alkyl halide preparation and Class 11, Unit 13 for alkene addition reactions ).

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