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Chapter 11: Q65P (page 591)

Trichloroisocyanuric acid, TCICA, also known as 鈥渟wimming pool chlorine,鈥� 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.)

Short Answer

Expert verified

The saturated carbon atom that has two other carbons containing a hydroxyl group is called secondary alcohol.This compound also has one hydrogen atom at the carbon that bears the hydroxyl group.

Step by step solution

01

About the secondary alcohol

The saturated carbon atom that has two other carbons containing a hydroxyl group is called secondary alcohol.This compound also has one hydrogen atom at the carbon that bears the hydroxyl group.

02

About TCICA

The abbreviation for TCICA is trichloroisocyanuric acid. This compound bears three nitrogens at the six-membered cyclic ring in which every nitrogen is attached to one chlorine atom. The remaining three carbons in the ring get attached to the oxygen atom through the double bond.

03

About the mechanism

The abstraction of proton from HCl takes place to form a cation that has resonance structures. On treatment with the given secondary alcohol will give the product. The complete sketch of the mechanism is given below.

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Most popular questions from this chapter

Propose mechanisms for the following reactions. In most cases, more products are formed than are shown here. You only need to explain the formation of the products shown, however.

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

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Show the alcohol and the acid chloride that combine to make the following esters.

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(b)

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(d)

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?
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