Acid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 H-O HO-
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- The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.Acid-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?Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.
- Give the product and mechanism for the reaction below. Br NaOEt (Base) AH3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br BrFrom the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH₂ Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O2, OH g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C2H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 j. Ph3P+-CH₂ k. pyridine, heat I. PhBr
- Propose a synthesis to convert 1-methylcyclopentene B to the cyclic ester C. Show all intermediates, and reagents necessary for each step.3. Treatment of 1-phenyl-2-propenone with a strong base such as LDA does not yield an anion, even though it contains a hydrogen on the carbon atom next to the carbonyl group. Explain. (a) Ethyl pentanoate H Ethyl 2-methylbutanoate CH₂ . Which of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. 1-Phenyl-2-propenone (b) Ethyl 3-methylbutanoate (d) Ethyl 2,2-dimethylpropanoatePropose a mechanism for the conversion of (S)-citronellal to isopulegol.
- Write a mechanism for the following reaction.Acetylenic fatty acids are found in many tropical plants. Compound H, C18H2502, is one such compound; it absorbs 5 equivalents of H2 when treated with H2 over a Pd/C catalyst. Ozonolysis of compound H produces the following products: pentanal (CH3(CH2)3CHO) 2-охоасetic acid (HOOCCHO) oxalic acid (HooccOOH) nonanedioic acid (HOOC(CH2)7COOH) Draw the structure of compound H. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. ..Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr 1 MeO B. H₂SO4, H₂O, HgSO4 E. Na₂Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 x I. TsCl, py The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR = MeO Ill. N Me Galanthamine OH
