Which product below would be most likely to form after treating 1-propanol with TsCI, py followed by LIAIH? O a. lithium 1-propoxide O b. 1-chloropropane O c. propane O d. propylaluminum chloride

QUESTION 2 The preparation of a Wittig salt from an alky halide and triphenylphosphine proceeds by a(n) O A. E2 O B. Sn2 OC. E1 O D. free radical O E. Sn1 mechanism. QUESTION 3 Which resonance structure is more reactive as a nucleophile? Ph Ph O A. 1 O B. 2 OC. both are equally reactive Click Save and Submit to save and submit. Click Save All Answers to save all answers. o search F10 F1 F2 F3 F4 F5 F6 23 2 3 4. 7 8 W Y UI

Which will complete the following reactions? Choices: A. HBr / ether B. PBr3 / ether C. SOCl2 / pyridine D. Br2 / NBS E. Chlorocyclopentane F. Cyclopentanol G. Iodobenzene

2. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate the proper stereochemical relationships between groups (if appropriate), and write the word "racemic" next to any compound that is formed as a racemic mixture. a. b. C. d. e. f. H3C H 2) H3O+ NaCN aq. NaOH NH NaOH H₂O, A CN 1) LiAlH4 2) H₂O HO CN H3O A g. Hic i CH₂ H3C NaCN aq. NH4Cl H3C. NH2 SOCI2 pyridine h. CN 1) PhMgBr H3C CH3 2) H3O+ i. H3C CN NaOH Ph CH3 H₂O j. 1) LiAlH4 N' Ph H 2) H₂O k. CN H3C H3O CH3 A I. OH 1) LiAlH4 Ph CN 2) H₂O m. H3C CN 1) i-Bu₂AIH CH3 Ph 2) H3O+ n. NH2 1) H3OA H3C CN 2) neutralize

Question 20

V: Convert the following from the indicated starting material and any other possible reagents: this might take more than one step. C a. b. HO. NH₂ Br شد to to to to O CN NIT OH

Which of the following provides the best description of the two products of the following ether cleavage? HBr, A a. two alcohols b. cyclic ether C. 2-propanol and 2-bromobutane d. 1-propanol and 2-bromopropane e. 1-propanol and 2-propanol f. 1-bromopropane and 2-propanol

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe? a. methyl iodide b. ethyl iodide c. 2-bromopropane d. tert-butyl chloride a O b O c O d

1. Which alkyl bromide is the best choice to use as a reagent in a Williamson ether synthesis of 2-propoxybutane? A Br A B OCH3 2. What is the product of this alkoxymercuration-demercuration reaction? B OCH₂ C H₂CO Br 1. Hg(OAc)2, CH3OH 2. NaBH4 C HyCO. D D

Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. r Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LiAlH₁ f. PBr3 b. H₂SO4 c. HCI d. HBr i. CH3 MgBr; then H3O+ e. SOC1₂ j. CH3 CH₂ MgBr; then H3O+ g. CrO3, H₂ SO4, H₂O h. NaH k. CH3 CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+t n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3