If the Favorskii rearrangement of 2-chlorocyclohexanone is carried out using sodium ethoxide in ethanol, the product is ethyl cyclopentanecarboxylate. -OEt .CI EtO-Na+ ELOH Propose a mechanism for this reaction.

10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from y-bisabolene by the following route: "Br* Bromonium Cyclic carbocation -H*) Base ion Bromo peroxidase Br y-Bisabolene 10-Bromo-a- chamigrene

Provide the name of the product after cyclopropanone reacts with methylmagnesium bromide and hydronium in THF:

Which is the first step of the reaction below? protonation of benzene protonation of nitric acid attack of the aromatic ring on nitric acid hydrolysis of sulfuric acid HNO3 ZON H2SO4 Which is the first step of the reaction below? OMe OMe disproportionation of bromine rearomatization of the aromatic ring after the nucleophilic attack attack of the aromatic ring on bromine deprotonation of the aromatic ring Br2 Br

conc. HBr HO. Br 2. (Ph)3C-OH HCI (Ph);C-CI H20 d = E1 Elimination e = E2 Elimination a = Proton transfer f = Sy1 Nucleophilic substitution b = Lewis acid/base c = Electrophilic addition g = SN2 Nucleophilic substitution The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 2.

Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethylcyclohexanol and butan-2-ol.

Cyclohexanone can be effectively oxidized to adipic acid by treatment with which two of the following compounds? O KMNO4 or HNO3 O HOCI or HNO3 O PCC or Na;Cry03 O LIAIH or NaBH4 O None of these choices

Identify the reagents nacessary to accomplish cach of the following transformations. Choose the correct reagents from the following list: CH;CH;COCI, AICI, Fuming H3SO4 CH:CH;CI, AICla SOCI, Pyridine dilute H,S0. Zn(H, HCI, heat (CH:)2CHC, AICI; HNO, HaSO4 Enter the correct letter for sach stap of the reaction in the boxes below. (Reagents con be usad more than once) Step A: Step B: Step C:

TMS ethers can be removed by treatment with fluoride ion as well as bv acid-catalyzed hydrolysis. Propose a mechanism for the reaction of cyclohexyl TMS ether with LiF. Fluorotrimethylsilane is a product.

Propose a synthesis of 4-cyclopentyl-1-butanol starting with cyclopentene and ethylene oxide as only carbon sources and any needed inorganic reagents: