Chemistry - STEREO ISOMERISM Question with Solution | TestHub
Adrenaline (epinephrine) is the hormone released into the blood in moments of stress; it raises heart rate and blood pressure and dilates the air passages.
(a) How many stereoisomers does adrenaline have ?
(b) The stereoisomer shown here is the one that is pharmacologically active. What is the configuration of each of the asymmetric centres ?
adrenaline : 
Options:
Answer:
Solution:
Ans. (a) 2 stereoisomers. (b) (R).
Sol. (a) Adrenaline, (HO)2C6H3-CH(OH)-CH2-NHCH3, has only one asymmetric centre (the carbinol carbon), so the number of stereoisomers is 21 = 2 : (R) and (S).
(b) At the carbinol carbon the priorities are OH CH2NHCH3 C6H3(OH)2 H (the CH2 attached to N outranks the aryl carbon). With H behind, the order OH CH2NHCH3 aryl runs clockwise : the active stereoisomer is (R).
