Draw the structure(s) of the major organic product(s) of the following reaction. 1. lithium diisopropylamide/ hexane Br 2.1 eq. You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr)₂. If no reaction occurs, draw the organic starting material. If substantial starting material is present at the end of the reaction, include it in the products. • 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. 85 ? ChemDoodle n [F 8c
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- Draw the structure(s) of the major organic product(s) of the following reaction. 1. lithium diisopropylamide / hexane 2. 1 eq. CH3I • You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(1-Pr)2 derived from N(i-Pr)2 ". • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. • 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. ed opy aste ChemDoodleDraw the structure(s) of the major organic product(s) of the following reaction. 1. NaOCH3 / CH3OH H3C CH3 2. 1 eq. 2-bromo-2-methylpropane • You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr),. • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. • 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. Draw the structure(s) of the major organic product(s) of the following reaction. Aqueous NaHCO3 0° C 1 eq. Cl2 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, draw both stereoisomers. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional…Draw the structure(s) of the major organic product(s) of the following reaction. 1. lithium diisopropylamide / hexane 2. 1 eq. CH3I • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, draw both stereoisomers. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr)2 . • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. 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.
- 3 Draw the structure(s) of the major organic product(s) of the following reaction. 1. lithium diisopropylamide/hexane 2. 1 eq. CH3-CH=CH-CI • You do not have to consider stereochemistry. Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr)2. • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom righ Separate structures with + signs from the drop-down menu. . . will ChemDoodle Y Jn [F 4Draw the structure(s) of the major organic product(s) of the following reaction. 1. KH / THF 20° C 2. 1 eq. H₂C=CH-Br You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)₂ derived from N(i-Pr)₂- If no reaction occurs, draw the organic starting material. If substantial starting material is present at the end of the reaction, include it in the products. 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. 90-85[Review Topics] [References] Draw the structure(s) of the major organic product(s) of the following reaction. 1. Ithium diisopropylamide /hexane Br 2.1 eq. • You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e g. HN(-Pr)) derived from N(-Pr),. If no reaction occurs, draw the organic starting material. •If substantial starting material is present at the end of the reaction, include it in the products. 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 P.
- 3. (Sections 19.6 and 19.7) Draw the mechanism for the Wolff-Kishner reaction in a., being sure to show all relevant lone pairs, charges, arrows, etc. Draw the major product formed in reactions b. and c. For all reactions, pay attention to stereochemistry and regiochemistry! jose H 1) H2N-NH2, acetic acid, H₂O/diethylene glycol 2) NaOH, 200 °C CH3 a. b. C=N H₂O H2SO4 CEN H₂O NaOH4. Explain the stereochemistry of the following reactions shown below of the products B & C (OR). 1. SO2CI /pyridine HO H 1.SOCI/ether 2. CH30 Na/CH,OH 2. CH;O Na/CH,OH (R)- (S)- (S)- A B 5. Provide a detailed mechanism for the following reaction. Draw the structures of the products. Explain your answer S). HI A B 6. Methylcyclopentanol on treatment with HBr gives 1-bromo-1-methylcyclopentane as a major product. Show a detailed mechanism to explain your answer . S). CH3 H3C Br HBr но- -H2O 2-methylcyclopentanol 1-bromo-1-methylcyclopentane CS Scanned with CamScanner4) Propanoic acid is a carboxylic acid. List four other propionic acid derivatives, and rank them in order of their expected reactivity toward nucleophilic acyl substitution. [self-study not grade: Which one is most likely used in Friedel-Crafts acylation? Which one is most likely used in alkylation reaction involving base (to deprotonate a-hydrogen) and alkyl halide? Why? What would an amide be synthetically useful for? ]
- Provide a 3-5 step synthetic route the target molecule from starting material A. Be sure to account for relative stereochemistry and suggest reagents/conditions for each step.Carboxylic acids are lowest in reactivity towards nucleophilic substitution. Why? (Consider the reaction between acetic acid and sodium methoxide).1) Give the MAJOR organic product(s) of the reaction, and include all stereochemistry as appropriate. Identify any meso compounds if they are made. 2) Indicate whether a solution of the product(s) would be optically active OR not active and provide a simple reasoning to support your choice. A. B. C. D. E. 1. BH3. THF 2. NaOH/H₂O2 H₂ Pd/C HBr ROOR Br₂ hv H₂ Pd/C