Interpretation:
The mechanism for the formation of mesitylene by heating acetone with sulfuric acid is to be proposed.
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.
舧 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
舧 A carbon-carbon bond formation occurs by aldol addition and aldol condensation reaction.
舧 An aldol reaction takes place by acid catalysis, and direct dehydration of
舧 A
舧 A chemical reaction that is catalyzed by n base is called base-catalyzed reaction.
舧 Aldol reaction is preferred in basic condition over acidic condition, as after the aldol condensation, acid catalysis promotes the reaction further.
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Organic Chemistry
- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardA 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_forward
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning