Predict the products formed by periodic acid cleavage of the following diols

(a)

(b)

(c)

(d)

Short Answer

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(a)

(b) (c)

(d)

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01

Diols

Diols can be categorized into vicinal and germinal diols. The two hydroxyl groups are connected to the same carbon atom in germinal diols. Vicinal diols comprise two hydroxyl groups connected to adjacent atoms.

02

Periodic acid cleavage of glycols

Glycols created by the dihydroxylation of alkenes are cleaved by the periodic acid (HIO4). The products generated in this reaction are ketones and aldehydes.The structures of unknown sugars can be identified by periodic acid cleavage.

03

Predicting the products formed by periodic acid cleavage of the following diols

(a)1,2-diol get subjected to cleavage in the presence of HlO4 to generate ketones and aldehydes. Butane-2,3-diol undergoes cleavage in the presence of HIO4to generate two equivalents of acetaldehyde. The reaction can be given as:

Periodic acid cleavage of compound a

(b)1-(hydroxymethyl) cyclopentanol undergoes cleavage in the presence of HlO4 to generate cyclopentanone and formaldehyde. The reaction can be given as:

Periodic acid cleavage of compound b

(c)2-phenylpentane-2,3-diol undergoes cleavage in the presence of HlO4 to generate acetophenone and propionaldehyde. The reaction can be given as:

Periodic acid cleavage of compound c

(d)Bridged 1, 2-diol undergoes cleavage in the presence of HlO4 to generate dialdehyde as the product. The reaction can be given as:

Periodic cleavage of compound d

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Most popular questions from this chapter

Unlike ethylene glycol, propylene glycol (propane-1, 2-diol) is non toxic because it oxidizes to a common metabolic intermediate. Give the structures of the biological oxidation products of propylene glycol.

A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the SN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.

(b) What would have been the best synthesis of (R)-2-ethoxybutane?

(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat

Predict the products of the sulfuric acid-catalyzed dehydration of the following alcohols. When more than one product is expected, label the major and minor products.

(a) 2-methylbutan-2-ol (b) pentan-1-ol (c) pentan-2-ol

(d) 1-isopropylcyclohexanol (e) 2-methylcyclohexanol

Trichloroisocyanuric acid, TCICA, also known as “swimming pool chlorine,” is a stable solid that oxidizes alcohols, following a mechanism similar to oxidation by HOCl. No reaction occurs between TCICA and the alcohol (in a solvent such as acetonitrile) until one drop of HCl(aq) is added, whereupon the reaction is over in a few minutes. Write the mechanism for this oxidation that shows the key role of the acid catalyst. Show the oxidation of just one alcohol, not three. (Hint: The carbonyls are the most basic sites on TCICA.)

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