Tertiary alcohols with two identical alkyl groups attached to the alcohol carbon can be made either from an ester and two moles of a Grignard reagent, or from a ketone and one mole of a Grignard reagent. Use retrosynthetic analysis to suggest one path of each type to synthesize 1,1-diphenylethanol. (Člick and drag Ester Grignard route 1 Н,о" OH or Ketone Grignard route 2 1,1-diphenylethanol 2 CH3MGB. -MgBr MgBr "ОСН, CH;CH,MgBr 2 CH;CH,MgBr CH;MgBr "ОСНЗ OCH3
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- Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● AAVII -85 ? ChemDoodleⓇ Y [FDraw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● VIL ? ChemDoodle Ⓡ Qt Sn [FDraw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 2-methyl-2-butanol as the MAJOR product. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu.
- МЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • You do not have to consider stereochemistry. • You do not have to explicitly draw Hatoms. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● 8) *9.8 MUIT / ? ChemDoodle [ ] removeAn important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
- 10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH3 Br CH3Draw structural formulas for organic products A and B in the window below. CH3 CH3CCH₂CI CH3 ● ● Mg ether // Draw only products having the organic portion of the original alkyl halide. Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. Separate products from different steps using the → sign from the drop-down menu. ? CH3OH A ChemDoodleⓇ B Sn [FWrite the Ky reactions for pyridine, for sodium 2-mercaptoethanol, and for cyanide. H+ binds to S in sodium 2-mercaptoethanol and to C in cyanide. (Hint: Spectator ions, which do not react in solution, appear on both sides of the reaction and can be removed.) N: HOCH.CHS: Na+ CN Pyridine Sodium 2-mercaptoethanol Cyanide Refer to the Ka values below for their conjugate acids. Which of the three bases shown above is the strongest? NH HOCH.CH.SH HCN Pyridinium ion K. = 6.3 x 10-6 2-Mercaptoethanol K. = 1.9 X 10-10 Hydrogen cyanide K = 6.2 x 10-10
- From the table of available reagents select the one(s) you would use to convert: 3-pentanol to 3-bromopentane. 3-pentanol to 3-methylpentane. Use the minimum number of steps; in no case are more than four steps necessary. List reagents by letter in the order that they are used; example: fa. Reagents available а. ВН3, ТHF; then H2O2, OH f. Н2, Pd b. Br2 g. Mg c. CH3MgBr; then H30+ h. NABH4; then H3O+ d. i. PB13 CrO3, H, SO4, H20 e. CH2=0; then H3O+ j. POC1 , pyridineDraw a structural formula(s) for the major organic product(s) of the following reaction. Br + CH3CH₂O™ Na* ethanol • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu.CH=CHNO₂ (2-nitrovinyl)benzene Electrophilic substitution on (2-nitrovinyl)benzene occurs at the meta position. Draw resonance structures to show how the ring is electron-poor at the ortho and para positions. You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu. 0 78 00-F k