Your Turn Which Mechanism is it? 5. In each of the problems below, consider the E1...
5. In each of the problems below, consider the E1 or E2 reaction occurs then show the mechanism and product or products. Label major and minor products where applicable. a. Reaction of 1,1-bromomethylcyclohexane and sodium ethoxide in ethanol Br CH, OH b. Reaction of (1R 2R) 1-bromo-2-methylcyclohexane and sodium ethoxide in ethanol. HINT: You should draw the ring in a chair conformation first. CHE + 0 *lller Сн, CH,CH-OH C. Reaction of (15,2R) 1-bromo-2-methylcyclohexane and sodium ethoxide in ethanol. HINT:...
Regioselectivity of E1 and E2 Reactions 3. The reaction between a 1,2-dimethylcyclohexanol and concentrated strong acid results in an E1 reaction. Show the first step in this reaction (consider that the acid catalyst can protonate the OH group which eventually can form H2O that can act as a good leaving group). а. сн, OH conc.H2SO4 CH3 b. What is the geometry at the reaction center of the intermediate? Show the final step and all possible alkene products с. State the...
4. The reaction between cis-1-bromo-2-methylcyclohexane and ethoxide (a very strong base) results in an E2 reaction. (refer to Mechanism 9.8 in your textbook) a. Show the transition state for this reaction. CHE + CH, CH, CH, OH b. Show the formation of the product(s) from the transition state. c. Use the rule from part 3d, to determine the major and minor alkene products.
For each of the following reactions, determine which ELIMINATION mechanism (E1 or E2) will occur. Alkyl Halide Substitution: Methyl 1° 2° 3° Base Strength: Strong Weak Mechanism Type: E1 E2 Draw the mechanism that leads to ALL products for the reaction. Finally, underline the major product of the elimination reaction: H3C OH H2C H2C1 Br CHE
For each of the following reactions, determine which ELIMINATION mechanism (E1 or 2) will occur. Alkyl Halide Substitution: Base Strength: Mechanism Type: 2° 3° Methyl Strong E1 1° Weak E2 Draw the mechanism that leads to ALL products for the reaction. Finally, underline the major product of the elimination reaction: NaOCH Challenge Problems: Synthesis: Predicted Ability: Good Average Poor Actual Ability: Good Average Poor Propose a synthesis from the starting material to obtain the indicated goal molecule. Note that any...
predict the mechanism (Sn1, Sn2, E1, E2) and major products for each reaction 8) NaOCHy CH,CHE CH,OH CH CH heat H,PO heat KOB HOIBU CHO CH, NaN. Br. H NaOCH CH3CH2OH heat dapted from Ruehl
1. Determine whether the following reactions will go through SN1, SN2, E1, or E2 mechanism a. 1-bromobutane + sodium hydroxide b. 2-chloro-2-methylpentane + sodium hydroxide + heat C. 2,3-dimethyl-3-bromopentane + water d. 2-bromobutane + methanol 2. Draw the major product for the following reactions (draw both products if racemic): NaSH DMSO TsO CHA Nal CH, acetone CH,CH,ONa+ ethanol CH,OH/H-0 Solite Nal (1 equiv.) acetone F CH2CH OH 25°C
25. Which two reactions will never go through an E1 or Se 1 mechanism? Why not? NaOCH V ICH,CH, OH CH,OH X Hyo 26. Substitution and elimination reactions always compete with each other. For each reaction below draw the probable substitution and elimination products, considering if a 1" or 2" order mechanism is likely. Then identify the major product 27. Draw the major organic product, then the curved arrow mechanism for each reaction, considering whether the major pathway should be...
the problems below tabel they had a marc ar.o . mechanism and product or products indicate stereacherywhere Reaction of bromopropane and sodium methode in methane CHO b Reaction of 2-bromopropane in ethanol -Br + CH CH OH Reaction of (R) 3-chloro-3-methylheptane in acetic acid ---CHE CH,COOH d. Reaction of the molecule shown with sodium methoxide in aprotic solvent CH H + OO. Na 0-CHE acetone
5. 10points. Determine which of substitution or elimination mechanism works best in order to form the major product of the following reaction? (hint: draw chair conformation for the molecule) CH3 NaOCHCH, CH,CH,OH "CH3 Hac CH3