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- How would you synthesize the following compounds from cyclohexanone using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Reagents a 1. CH3MgBr/dry ether 2 H3O+ e 1. OsO4 i 1. BH3/THF 2. NaHSO3/H2O 2. H₂O₂ / NaOH b 1. C6H5MgBr / dry ether f 1. NaBH4 j Mg / dry ether 2 H3O+ 2. H3O+ с PBr3 g HOCH2CH2OH/HCI k H2/Pd d m-chloroperbenzoic h H3O+ / heat I CrO3 / H3O+ acid m cyclohexanone a) cyclohexylbenzene b) 2-phenylcyclohexanone Submit Answer Try Another Version 3 item attempts remainingHow might you carry out the following selective transformations? (Note that a protection step may be required, and recall that aldehydes are more reactive than ketones toward nucleophilic addition.) Syntheses may require several steps. Choose the route with the fewest steps. Use letters from the table to list reagents in the order used (first at the left). Example: dag a) Reagents a 1. excess NaBH4 2. H3O+ e 1. Li(CH3)2Cu 2. H3O+ b 1.1 eq. NaBH4 2. H3O+ f 1. CH3MgBr / dry ether 2 H3O+ C 1. LiAlH4 d. 2. H3O+ aqueous HCI g HOCH2CH2OH/HCI HO CH3 h Trimethylsilyl chloride / triethylamine i CrO3/H3O+ j Dess-Martin periodinane in CH2Cl2 Previous Next>How would you synthesize the following compounds from cyclohexanone using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Reagents a 1. CH3MgBr / dry ether 2 H3O+ e 1. OsO4 i 1. BH3/THF 2. NaHSO3/H₂O 2. H₂O₂ / NaOH b 1. C6H5 MgBr / dry ether f 1. NaBH4 j Mg / dry ether 2 H3O+ 2. H3O+ C PBг3 g HOCH2CH2OH/HCI k H2/Pd d m-chloroperbenzoic h H3O+ / heat 1 CrO3 / H3O+ acid a) 2-phenylcyclohexanone b) cyclohexylbenzene m cyclohexanone
- 1. Br₂, PBrg 2. H₂O H₂C OH 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 α- 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 H3C :0: :0::Br: Br Br H3C CO-P H Br BrAcyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C NH₂ HCI/H₂O reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one.From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH,CH,CO,H 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 b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C₂H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br j. Ph3P+--CH₂ k. pyridine, heat I. PhBr
- Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 Li :Base T H-O: Li Lithium hydroxide (LiOH) three steps Lithium acetylide Draw the structure of lithium acetylide. Draw Your Solution di. Η Η Η Η | | | | H-C-C-C-C: II HH HH Butyllithium (BuLi) OR CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe H3C H H₂C many steps Li HO OH I (+)-Acutiphycin CH3 CH₂ "OHE Write out all the steps in the mechanism of this electrophilic aromatic substitution reaction. Include all resonance contributors. CH3CI Benzene → acetophenone AICI3 . Show the steps necessary, in order, to make each of the following compounds. Start with benzene, and use only reactions we studied this semester. ECHECH CH3 b) c) NOzDraw the structure(s) of the major organic product(s) obtained after workup of the following reaction. о + сн CH₂-C-Cl CH3 1. in benzene 2. aqueous HCI You do not have to consider stereochemistry. • . If no reaction occurs, draw the organic starting material. • • • Include the amine from which the enamine was derived. Include counter-ions, e.g., Na+, I, in your submission, but draw them in their own separate sketcher. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Θ CH3 CH3 CH3 ? ChemDoodle" remove
- Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I-, in your answer. In cases where there is more than one answer, just draw one.a. When a carboxylic acid is dissolved in isotopically labeled water (H218O) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this. b. If a carboxylic acid is dissolved in isotopically labeled methanol (CH318OH) and an acid catalyst is added, where will the label reside in the product?c. If an ester is dissolved in isotopically labeled water (H218O) and an acid catalyst is added, where will the label reside in the product?H3C 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 Br