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- The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OHWhich is the major product from the acid catalyzed hydrolysis of cyclohexene oxide? но OH но он || II IVThe product from the following reaction in acidic medium is: CH CH-COH OH CH, OH CH3 CH3 OH CH3 OH OH OH 3.
- What is the major organic product obtained from the following reaction? CI O O CH,COONa DMSO OMe OCOMe OH OHWhich compound is the major product of the reaction below? HO OH 11419 HO, он TSOH (cat) (A) (В) (D) (C) O Compound B Compound D Compound C Compound A● Provide the major organic product of the following reaction A B OC OD .COH DNIÊN 2) 8,0 coM D
- Identify the product of the following reaction; axidation ? OH но.The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.
