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Chapter 11: Q24P (page 567)

Contrast the mechanism of the two preceding reactions, the dehydration and condensation of ethanol.

Short Answer

Expert verified

There are numerous dehydration reactions. Some of them are nitrile formation and ketene formation. The dehydration of primary amides generates a nitrile.

Step by step solution

01

Dehydration

There are numerous dehydration reactions. Some of them are nitrile formation and ketene formation. The dehydration of primary amides generates a nitrile.

02

Bimolecular Condensation

An alcohol molecule may strike a protonated primary alcohol to get subjected to an SN2 displacement reaction. This results in bimolecular dehydration forming an ether. This is an example of a condensation reaction.

03

Mechanism of the dehydration and condensation of ethanol

Both the mechanisms start with the protonation of oxygen.

The protonation of the oxygen atom

Another ethanol molecule functions as a base in one mechanism leading to elimination reaction.

Elimination reaction where a molecule of ethanol serves as a base

Another molecule of ethanol serves as a nucleophile in the other mechanism leading to a substitution reaction.

Substitution reaction where a molecule of ethanol serves as a nucleophile

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Most popular questions from this chapter

Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa= -2.6) is a much stronger acid than acetic acid (CH3COOH,pKa =4.8)

Propose a mechanism for the reaction of

(a) 1-methyl cyclohexanol with HBr to form 1- bromo-1-methylcyclohexane.

(b) 2- cyclohexylethanol with HBr to form 1-bromo-2-cyclohexylethane.

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

(a)

(b)

(c)

(d)

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

(a)chromic acid

(b)PCC(pyridinium chlorochromate)

(c)sodium hypochlorite/ acetic acid

(d)DMSO and oxalyl chloride

(e)DMP(periodinane)reagent

Give the structures of the products you would expect when each alcohol reacts with

(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.

(a) butan-1-ol (b) 2-methylbutan-2-ol

(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol
See all solutions

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