Concept explainers
Interpretation:
A mechanism for the conversion of the
Concept introduction:
Attack of the nucleophile, triphenyl phosphine, on the epoxide obtained from a trans alkene, opens up the ring. Free rotation is possible in C–C bonds. The rotation of the C–C single bond and subsequent removal of triphenylphospheneoxide will yield the cis product.
To propose:
A mechanism for the conversion of the epoxide (obtained by treating a trans alkene with peracids) into cis alkene by treatment with triphenylphosphine.
Trending nowThis is a popular solution!
Chapter 19 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- 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.arrow_forwardAcid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forward
- The Favorskii reaction involves treatment of an -bromo ketone with base to yield a ring-contracted product. For example, reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.arrow_forwardSolvolysis of the following bicyclic compound in acetic acid gives a mixture of products, two of which are shown. The leaving group is the anion of a sulfonic acid, ArSO3H. A sulfonic acid is a strong acid, and its anion, ArSO3, is a weak base and a good leaving group. Propose a mechanism for this reaction.arrow_forwardShow the products you would obtain by acid-catalyzed reaction of cyclohexanone with ethylamine, CH3CH2NH2, and with diethylamine, (CH3CH2) 2NH.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning