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- 18.26 Predict the products of the following ether cleavage reactions: LOCH CH3 OC(CH3)3 (a) HI CF3CO,H, ? (b) H2O HI HI (c) Н,С— СНОСH,CH, (d) (CH3);CCH,OCH,CH3 H20 H2O(13) A B C OD What is not an elementary step in the mechanism for the following reaction? H₂O НО. (A) loss of iodide to generate a carbocation (B) 1,2-methyl shift/rearrangement (C) nucleophilic attack by water (D) proton transfer D. You selected this answer.Which of the following are a major product of the reaction sequence shown belo (1) Br2, FeBr3 (2) Mg/ether он он (A) (B) (3) (4) dil H* /H;O (C) (D) он Compound C Compounds B and D OCompounds A and B Compound D
- 15.34 Coriolic acid, isolated from the hearts of cows, is of interest because of its ability to transport calcium ions through membranes. It was synthesized by the following sequence of steps. Supply structural formulas for the compounds designated by letters. HO(CH₂), OH H HC C-C F C-CH₂OH H C+B D HBr (48%) (1 equiv) H₂O H₂O+ cold CH,(CH₂),CH,MgBr (2 equiv) diethyl ether tetrahydrofuran E A CrO₂, H₂O H₂SO acetone Li*NH, (2 equiv) NH,(liq) tetrahydrofuran oxidizing agent similar to NH,C, HO G B H CrO,CI F18.18 Provide a structural formula for the product from each of the following reactions. (a) (c) (e (1) LDA (2) CH,CH,I NaH CI (b) (d) O. (f Br, CH,CO,H Br, (excess), NaOH18.35 Draw the most likely mechanism for each of the following transformations: Br OH Br Br2 FeBr, 1) NaOH, 350°c 2) H,0* (a) (b) O2N O2N. 1) NaNH, 2) H,O" (c) NH2
- 19.60 Draw the major organic products for each of the following reactions. (a) (b) OEt LOCH3 Pd(PPH3)4, NaOH EtO Pd(PPh)4, NaOH -? THE THE (c) (d) Pd(OAc)2 Pd(OAc)2. ? PPH3,EtgN ? PPH3,EtgN Br16.14 Identify the reactants you would use to prepare each of the following compounds via a Diels-Alder reaction: (a) CN CN (b) H (c) CHO (d) CO₂Et CO₂Et + EnProblem 8.16d Indicate which of these terms can be used to describe the first step of the following reaction. More than one term may apply.
- (7) (8) H3C OH H + CH3OH - H₂O HCI catalyst + 2 CH3CH₂OH - H₂O HCI catalyst15.36 Phenylethylamine is a natural substance that is structurally similar to amphetamine. It is found in sources as diverse as almond oil and human urine, where it occurs at elevated concentrations as a result of stress and certain forms of schizophrenia. One method of synthesizing the compound for pharmacological and psychiat- ric studies involves two steps: H2 -CH2-CI + NaCN -CH2-C=N Pt -CH,-CH,-NH, phenylethylamine Classify each step as an addition, elimination, or substitution.(11) A OB C D A solution of which of the following alkyl halides in methanol will be optically active to begin but slowly lose most or all of its optical activity when heated? H H Br H3CBr Br (B) (A) T Br (C) (D)