a) LiAlH4, then H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+ is to be predicted.
Concept introduction:
To predict:
The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+.
b) N-Bromosuccinimide in CCl4
Interpretation:
The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4 is to be predicted.
Concept introduction:
N-bromosuccinimide in CCl4 is used for introducing a Br in the benzyl carbon.
To predict:
The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4.
c) CH3MgBr in ether, then H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+ is to be predicted.
Concept introduction:
Grignard reagents will react with the carboxyl hydrogen to yield
To predict:
The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+.
d) KMnO4, H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+ is to be predicted.
Concept introduction:
When treated with KMnO4 in the presence of H3O+, the side chain in
To predict:
The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+.
Trending nowThis is a popular solution!
Chapter 20 Solutions
Organic Chemistry
- When a mixture of ketone 11 and \alpha, \beta - unsaturated carbonyl 12 are exposed to substoichiometric amounts of NaOMe, product B is obtained selectively. Subsequent treatment of B with excess NaOMe leads to the exclusive formation of tricyclic product 13. (1) Suggest a structure for B and provide a reason for its selective formation. (ii) Provide a reaction mechanism for the formation of 13, which accounts for its selective formation.arrow_forwardThe sex pheromone of the common house fly has the molecular formula C23H46. It can be synthesized in the lab using the following synthetic sequence. Give the structures of the pheromone and the intermediates A and B. n-C13H27C≡CH + n-butyl lithium → A (C15H27Li) A + n-C8H17Br → B (C23H44) B + H2 with Lindlar catalyst → the pheromonearrow_forwardThe treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.arrow_forward
- Give a rearrangement reaction equation to synthesize N-ethyl-2-methyl-buthylamide from the corresponding α-diazoketone. Give the structures of all intermediary products. Do not give a mechanism.arrow_forwardAnilinium ion, PhNH3+ , Catalyze semicarbazone formation from benzaldhyde much more effectively than would be expected on the basis of its strength as an acid. Explain.arrow_forwardDiethyl carbonate serves as a less-toxic alternative to phosgene for making Lexan. Propose a mechanism for the transesterification of diethyl carbonate with bisphenol A, catalyzed by a trace of sodium ethoxide. What small molecule is given off in this condensation?arrow_forward
- One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.arrow_forwardFollowing 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_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forward
- The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardThe following transformation involves a series of four consecutive Heck reactions and the formation of the four-ring steroid nucleus (Section 26.4) as a racemic mixture. Propose structural formulas for the palladium-containing intermediates involved in this reaction.arrow_forwardBenzenediazonium carboxylate decomposes when heated to yield N2, CO2, and a reactive substance that can't be isolated. When benzenediazonium carboxylate is heated in the presence of furan, the following reaction is observe. Propose a structure for the intermediate in this reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning