1. B. Supply the missing arrows to complete the reaction mechanisms below. For each of the reactions, BOX the electrophile and ENCIRCLE the nucleophile. H3C H. H. H3C H. CH3 CH3 H3C H. CHa 2. H2C HgC CH2 H. :0: :-H + H3C 3. + :Br: H.
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- Can you match best nucleophile / conditions that will give a successful hydrolysis reaction for each electrophile? 1. Acid chloride 2. Acetic anhydride 3. Ester 4. Amide a. LiAlH4; hydronium work-up b. PCC c. NaH d. CrO3 e. HOEt f. H3O+ or OH- g. H2O h. NaBH4;hydronium work-up5. Predict the major product, which will be formed under the depicted reaction conditions. Be sure to indicate stereocher clearly when relevant. d. HN, pyr е. Nao (cat.) OEt НО f. HCI, H20 HCI, H20 Ph heat HCI, NH3 H. then NaCNEACTIVE Circle the better nucleophile in polar protic solvent. Below each answer, BRIEFLY explain your choice. a. Cl- and -I b. CH3SH and CH3OH DIVSO page 14 of 17
- 2. Но ... H-O Draw the major product of this reaction. Explain your reasoning. Br₂, H₂O EtOH 1. Me₂ BuSi-CI, imidazole 2.9-BBN-H (like BH3) 3. H₂O₂, NaOH OTMS excess HBrIn this reaction, which species acts as the electrophile? Click on a letter A through D to answer. CH3 H3C CH3 H3C OH H3C-N-B-H H B. HH CI4 CH3 CC4 H3C CH3 H3C eH H3C-N-B-H H3C H B HH А. В. C. D.Which of the following nucleophiles would add to an alpha, beta- unsaturated ketone via direct addition? a. KCN b. LICH; с. КОН d. NH.CH.CH,СH. e. HOCH;CH:CH: ABC DE O O O O O
- - 1. Which of the following compounds would NOT produce the same major product as the others when treated with HCI? LIV b. C. II || IV III II d. e. III 2. Which of the following, when treated with HBr, would result in the formation of the same major product at both low and high temperatures? ||| v IV e. I V IV V*4. 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. A. Br NaSEt DMF В. ELOH C. .SO2NHNA Cl + D. NaH Br- HO, DMFRank the nucleophiles in each group in order of increasing nucleophilicity.a. -OH, -NH2, H2Ob. -OH, Br-, F- (polar aprotic solvent)c. H2O, -OH, CH3CO2-
- 1. Identify each move below as attack, leave, protonate (or deprotonate), or rearrang e. A. B. н- но- O-H н.8н н,о° +] D.[ E. F.Choose the most correct set of reagents for the following reactions. 1. ? a O b O C O 으으 OH 2. ? OMe a. 1. MsCl, pyridine; 2. NaOCH3, CH3OH b. 1. HCI, pyridine; 2. NaOCH3, CH3OH c. 1. PCI 3, SOCI2; 2. NaOCH3, CH3OH d. 1. TsCl, pyridine; 2. NaOCH3, CH3OH e. 1. CH3O-, pyridine; 2. H* f. 1. Pl3, pyridine; 2. -OCH36. Provide the structure for the major product in the following reactions. b. P f. OH g. Lia * Oia ملی CI 1. SOCI₂, pyr. 2. to Br 2 1. LIAIH4 (xs) 2. H₂O 1. LIAI(OR) 3H 2. H₂O 2. NH₂ Et₂CuLi 1. EtMgBr (xs) 2. H₂O 1. Mg 2. CO₂ 3. H* 4. SOCI₂, pyr 1. [H], NaBH3CN, EtNH₂ CI pyridine