Reaction of the glycol with periodic acid gives a fivemembered cyclic periodate. A cyclic perriodate

Short Answer

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Question: Describe the reaction mechanism of glycol (ethylene glycol) with periodic acid to form a five-membered cyclic periodate. Answer: The reaction of glycol with periodic acid involves the following steps: 1. Each hydroxyl group from ethylene glycol attacks the iodine atom in periodic acid, forming bonds between the oxygen and iodine atoms. 2. The L➤H-O-IO3 bond breaks, generating a positively charged iodine and a water molecule as a leaving group. 3. The oxygen connected to the iodine forms a bond with the positively charged iodine atom, creating a five-membered ring with a periodate structure. 4. Rearrangement of the periodate in the ring occurs through the migration of a double bond, producing the final five-membered cyclic periodate.

Step by step solution

01

Identify the molecules involved in the reaction

The first step is to recognize the molecules involved in the reaction. Glycol refers to ethylene glycol, which has the chemical formula HO-CH2-CH2-OH. Periodic acid is HIO4, a strong oxidizing agent that can cleave carbon-carbon bonds in certain molecules.
02

Understand the general mechanism of the reaction

In this reaction, a molecule of ethylene glycol will react with a molecule of periodic acid. The two hydroxyl groups (-OH) on the ethylene glycol are susceptible to the oxidizing action of the periodic acid, leading to the cleavage of the carbon-carbon bond and the formation of a five-membered cyclic periodate.
03

Draw the structures of the molecules involved

Before illustrating the reaction mechanism, it's essential to draw the structures of the molecules involved. Ethylene glycol (glycol): HO-CH2-CH2-OH Periodic acid (HIO4): ``` O || I-O-H || O ```
04

Illustrate the reaction mechanism

Here we'll show the step-by-step reaction mechanism between ethylene glycol and periodic acid. 1. Two lone pairs of oxygen from each hydroxyl group of ethylene glycol attack the central iodine atom of periodic acid, forming a bond between both oxygen and iodine atoms. ``` O || H-O-CH2-CH2-O-H + H-I-O-H ---> H-O-CH2-CH2-O-H | | || I O I-O-H || O ``` 2. The L➤H-O-IO3 bond breaks, leaving the iodine with a positive charge and creating a water molecule as a leaving group. ``` O || H-O-CH2-CH2-O-H || | || H-IO3 O-I (+) ``` 3. The oxygen that is still connected to the iodine forms a bond with the positively charged iodine atom, creating a five-membered ring with a periodate structure. ``` O || H-O-CH2-CH2-O-H \ \ I====O || O ``` 4. Rearrangement of the periodate in the ring through the migration of a double bond, resulting in the final five-membered cyclic periodate. ``` O || O-I-CH2-CH2-O-H \\ | || --O--- ``` This is a detailed explanation of how the reaction of glycol (ethylene glycol) with periodic acid leads to the formation of a five-membered cyclic periodate.

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