Question

ES Click the "draw structure" button to launch the drawing utility. Draw the principal organic product for the following reaction. 49 СН3СН-СН-СН-СН-СН-СН2ОН PCC — CH2C12 draw structure...

Answer 1

The first reaction given is a general oxidation of a primary alcohol by Pyridinium Chloro Chromate (PCC).

1o-alcohols on reacting with PCC convert into aldehydes.

Thus, the seven carbon primary alcohol, Heptanol coverts into a seven carbon aldehyde, 1-heptanal on oxidation with PCC.

CH2Cl2 (Dichloromethane) is a solvent used to carry out oxidation.

The line structure structure of heptanal and the reaction is given in the uploaded image.

CH₂Cl2 CH₃ CH₂ CH₂ CH₂ CH₂ CH₂ CH₂ Olt - Pec Heptanol CH₃ CH₂ CH₂ CH₂ CH₂ CH₂ CHO 1- Heptanal PCC oxidation of an aldehyde (-CHO). alcohol (=CH₂OH) to an s, que te o cu cy), СН2О OH mechanism 3 Nucleophile attack from less hindered sile (from solvent) 044 CHO CH₂ - C (CH₂) Product.

18. The correct answer is A.

This can be concluded from the mechanism of the reaction which is given in the uploaded image.

The reactant is an epoxide which can be opened at two positions. At one side there of the epoxide there are two methyl substituents and hence methoxide ion (CH3O-), the nucleophile feels more steric hinderance to attack at that that site. Thus, there is no possibility of epoxide opening from that site. The another side of the epoxide is favourable for the nucleophilic which is without any substituents. Thus, the nucleophile attacks from that less hindered site giving the major product.