10. Consider the two Wittig reactions below. The first Wittig reaction goes well. The second doesn't go at all. 1) Draw the structure of the ylide needed for this reaction. 2) Explain briefly why the second reaction fails. (Hint: The Wittig reagent, in addition to being a good nucleophile, is a very strong base.) Facile reaction CH2 No Reaction CH2
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- 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OHAn SN2 mechanism takes place when 3-(bromomethyl)pentane is added to each nucleophile listed below. Which nucleophile will also require an acid-base step after the substitution step in order to produce a neutral (not charged) product? A. LiN(CH3)2 B. NaI C. KN3 D. HSCH3 (Please type answer no write by hend)Circle the electrophilic and nucleophilic atoms in each substitution reaction below. Provide the neutral organic product; where a stereocenter is created, use a wavy bond to indicate a mixture of configurations or wedges/dashes for stereospecific reactions. Also, provide the dominant reaction mechanism (SN2 or SN1) somewhere in each box. E. 文 HCI HO. OH F. NANHTS H3C, DMF
- C. Draw a structural formula for the substitution product of the reaction shown below. CH;OH D. In both examples below the reactants shown are combined to bring about a nucleophilie substitution (S1, S,2) and/or elimination (E1, E2) reaction. What is the major reaction that takes place in each case? CH, CH,CH,CCH, NaOCH,CH, CH,CH,OH Nal -Br acetone3. Draw all products for the following reactions. For your products, write whether the nucleophile added to the Re face or Si face of the starting material. a. HO b. 1) LIAIH 2) H™ 1) CH3CH2Li 2) H+ c) Determine whether the nucleophile added to the Re face or Si face of benzaldehyde.10. Explain the reaction shown below. Include the following pieces in your explanation. Identify the electrophile and the nucleophile. Draw a curved arrow mechanism for this reaction. (Assume an acidic work-up). Explain the electron flow. Indicate any regiochemical or stereochemical preferences. one b. c. d. LIAIH4 OH one
- Polar aprotic solvents enhance the rate of an SN2 reaction by stabilizing the cations and the anions. changing the polarizibility of the nucleophile. raising the energy of the nucleophile. O lowering the energy of the nucleophile. Save for Later5. Predict the major product of the following reactions. A. + HBr В. HBr C. + H Br 6. Use curved arrows to show to show the mechanism of the reaction C above. Nucleophiles and Electrophiles 7. Label the electrophile and nucleophile in each step of the mechanism for question 6.Identify the reagents needed to come up with the given compounds. Pls Separate the reagents with a comma and a space. (ex. HNO3, H2SO4). For a multi-step reaction, separate the reagents with a semi-colon. (ex. HNO3, H2SO4; CH3Cl, AlCl3) There should be 9 reagents
- 3. Reactions. Suggest reagents for steps a-d in the following synthetic sequence CH3 CH3 CH3 b. a. HO CH3 CH3 но, LDA or strong base CH3 CH3 CH .CN с. но. CN d. CH3 H3C CN H3C CN Draw the major product of the following reactions H3C. 120 °C CN (no need to show stereochemistry) H2 (gas) cat. Pd (show relative stereochemistry)Choose the reagent(s) that would be most likely to complete this reaction. T OH A B C D E 1. OsO4 (catalytic) 2. NMO Br2 H₂O 1. Hg(OAc)2, H₂O 2. NaBH4, NaOH RCO3H 1. BH3-THF 2. H2O2, NaOH Ⓒ DoneIdentify the sequence of reactions that successfully completes the following transformation. Ph A. 1. BH3 2. H₂O₂ / NaOH _3. P, l₂ B. HI, ROOR, hv C. 1. HBr, ROOR, hv 2. Nal, acetone D. Choices A and C Ph