Chapter 11, Problem 45P

Interpretation Introduction

Interpretation:

The structure of Dibenzo-18-crown-6 is to be given and a plausible mechanism for its formation is to be provided.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has unpaired electrons, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The Williamson ether synthesis involves the reaction between an alkyl halide and an alkoxide or phenoxide anion to develop an ether. Among the two different hydrocarbon parts attached to the oxygen atom, one alkyl group comes from the alkyl halide and another alkyl/aryl group is a part of the alkoxide/phenoxide anion used in the synthesis.

In this protocol, Benzene-1,2-diol serves as the phenoxide part, which reacts with the chloroether to produce the cyclic crown ether.

The compound Dibenzo-18-crown-6 is formed when the compound catechol and bis(chloroethyl) ether react in the presence of sodium hydroxide.

The compound Dibenzo-18-crown-6 is a compound that has a strong complexing ability and also has a high affinity towards the alkali metal cations.