Using organic chemistry knowledge, draw the structures of compound (A), (B), (C)

Question

Using organic chemistry knowledge, draw the structures of compound (A), (B), (C), (D), (F).

C8H16O(A) does not react with either Br2/CH2Cl2 or cold basic KMnO4. (A)'s IR spectrum has a strong broad peak at 3300-3500cm-1. (A) cannot be resolved into enantiomers. (A) does not react with bleach to produce carbonyl product, but it rapidly reacts with ZnCl2/HCl to yield an organic chloride.

(A) reacts with H3PO4 and added heat to produce (B) and (C). (B) and (C) both reacts rapidly with Br2/CH2Cl2, discharging the red-brown color of the bromine.

Reacting (B) with ozone and then with zinc and water produced two products. Both products showed strong IR peaks around 1700cm-1 but only one of the product further oxidized with K2Cr2O7 to give a carboxylic acid. (B) reacts with HBr in the presence of organic peroxides to produce (D). In both reactions with AgNO3 in ethanol and with NaI in acetone, (D) reacted and precipiated.

When (C) was reacted with ozone followed by with zinc and water, (E) was produced. (E) also had strong IR peak around 1700cm-1 and was able to be oxidized with K2Cr2O7 to produce carboxylic acid.

(F) was produced from catalytic hydrogenation of (C). The parent ion in a mass spectrum of (F) has a nominal mass of 112.

Explanation / Answer

A is an alcohol,2,2,3,3-tetramethylbutan-1-ol.on reacting with ZnCl2 and HCl, OH is relpaced by Cl.on reaction with H3PO3 it will dehydrate to 2233tetramethylbutene.which on further reaction with 03,convert into caroxylic acid and alcholol again.

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