The spicy flavor of cayenne pepper is due mainly to a compound called capsaicin.
ID: 529218 • Letter: T
Question
The spicy flavor of cayenne pepper is due mainly to a compound called capsaicin. Its laboratory synthesis is given below. Draw the structure of compound A - D, as well as the structure of capsaicin. I am curious to know whether you think that having a Final Exam for the laboratory portion of Organic Chemistry. It was a valuable exercise. Please share your thoughts on the matter, CHE 224A students should express their thoughts on the most memorable organic lab experiment they did at their home institution.Explanation / Answer
The compound A is (CH3)2CHCH=CHCH2CH2CH2Br is (C8H15Br) a is bromo derivative of the starting hydroxy compound.
The compound B is (CH3)2CHCH=CHCH2CH2CH2CH(COOH)2 is C11H18O4 is a dicarboxylic acid from reaction and subsequent work up of the alkylated product on reaction with diethyl malonate sodium.
The compound C is (CH3)2CHCH=CHCH2CH2CH2CH2COOH is C10H18O2 is a mono carboxylic acid formed by decarboxylation of compound B at elevated temperature.
The compound D is (CH3)2CHCH=CHCH2CH2CH2CH2COCl is C10H17OCl is the acid chloride formed by the reaction of mono carboxylic acid with thionyl chloride.
The compound Capsiacin, (CH3)2CHCH=CHCH2CH2CH2CH2CONH(4-hydroxy 3- methoxy benzylic), formed by the reaction of acid chloride with 3-methoxy 4-hydroxy benzyl amine
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