11 - ORGANOSULFUR CHEMISTRY 2

Question 1

what is a sulfoxide?

Answer 1

Question 2

what is (S)-Esomeprazole?

Answer 2

treatment of dyspepsia, peptic ulcer disease, gastroesophageal reflux disease and zollinger elison syndrome

Question 3

what is (R)-Armodafinil (nuvigil)?

Answer 3

stimulant like drug used to treat depression and fatigue

Question 4

how do you go from a ROH to a sulfoxide?

Answer 4

Question 5

how do you prepare optically active sulfoxides?

Answer 5

via resolution of diastereomeric sulfinate esters

Question 6

what is the enantiomeric excess equation?

Answer 6

Question 7

why does sulfur stabilize carbanions?

Answer 7

pKa is lower than alkanes, so sulfur stabilizes carbanion
despite the electron repulsion between the S and the carbanion, the charge is accommodated because:
higher polarizability of sulfur allows for easier distortion of its electron cloud as it accommodates for carbanion
direct interaction of a lone pair of S with the metal cation (when using BuLi), which provides stability

Question 8

what is the corey seebach reaction?

Answer 8

basically, the S-S crossed part gets replaced by a carbonyl oxygen

Question 9

how are epoxide rings made starting from R-S-R?

Answer 9

Question 10

how can DMSO be used to make an epoxide ring?

Answer 10

Question 11

what is juvenile hormone?

Answer 11

insect hormone which insures growth of the larvae but prevents metamorphosis into adult insect (used as insecticide) made from isoprene

Question 12

part 1 of synthesis of juvenile hormone

Answer 12

Question 13

synthesis of juvenile hormone second part

Answer 13