Question

For O. Chem lab titled: "Perfumes: The Synthesis of Nerolin". Please answer questions 16 (a-c) and 17.

Nerolin chemically is called either 2-ethoxynaphthalene or ethy! S-naphthy! ether and can be prepared by the following Williamson synthesis of ethers. OH O-CH.CH - 1-CH.CH KOH alcohol +H.O+KI Waphthal Ethyl iodide Nerolin The potassium hydroxide, acting as a base, removes the slightly acidic proton from 6-naphthol and converts it into the nucleophile potassium B-naphthoxide, which attacks ethyl iodide and displaces the iodide ion. O-CH.CH CH-1 -1° CH, This last reaction occurs by an 5 2 (a bimolecular nucleophilic substitution) mechanism. In this mechanism, the rate of the reaction depends on the concen- tration of both reactants and involves the B-naphthoxide ion attacking the ethyl iodide molecule from the rear, thus avoiding the departing iodide ion. H HH H 8- CH, Transition state H -H CH,