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- 4. Using arrows to show electron movements, write the stepwise mechanism for the formation of the main reaction product in the following reactions: (a) 1) CH₂MgBr, Et₂0 2) H3O+ HCI ? ? (b) O Br (Ph)3PCH₂CH₂Ph Li THF, -70 deg C to r.t. ? (c) O 1) LiAlH4, Et₂0 2) H3O+ 3) NaOH 4) CH₂ Br ?2. For the following amines A and B, show all of the Hoffman elimination products. If one product is favored, please indicate it as the major product. 8. IZ: A.Provide a name for the following molecules. i. i. -N O i. = 3-oxo-N,N-dimethylamine ii. = 1-methylbutanamine O i. = 4-(N,N-dimethylamino)butan-2-one ii. = 1-methylbutanamine Expand O i. = 4-(N,N-dimethylamino)butan-2-one ii. = N-methylbutanamine O i. = 3-oxo-N,N-dimethylamine ii. = N-methylbutanamine %3D ZI
- Draw structures 1 and 2. CI Zn(Hg) H 2 HCI 1. Compound 2 is an isomer of 1. 2. 'H-NMR 7.16 (m, 4H), 3.16 (1H), 2.84 (2H), 1.95 (2H), 1.26 (d, 3H). Create OscerSketch Answer 1 Provide the products of the first and second reaction. H3C Na/NH3/ELOH O3/(CH3)2S Create OscerSketch Answer 21. Given the following 'H NMR spectra. А. Draw structure of compound. В. Label peaks (Ha, Hb, He, etc.) and indicate multiplicity Acetamide 11 10 7 6 5 4 3 1 ppm HSP-04-989 N. 005. a. Propose a method for how you would resolve (+)-2-chloropropanoic acid [(+)-RCOOH] using (-)-amphetamine [(-)-RHN₂] as the resolving agent. b. Do the same for N CH3 CH3
- 11) In electrophilic aromatic substitution reactions the nitro group is: A) a m-director since it destabilizes the meta sigma complex more than the ortho, para. B) a m-director since it destabilizes the meta sigma complex less than the ortho, para. C) an o,p-director since it stabilizes the ortho, para sigma complex more than the meta. D) an o,p-director since it stabilizes the ortho, para sigma complex less than the meta. E) none of the above.Why does the melting point (70-71) above match neither the enantiomers’ nor the racemate’s? Does it mean that the substance is impure, or perhaps isn’t even ibuprofen at all? (Racemic mixture:75-77C, Enantiomer:52-53C)2. Which of the following complexes cannot perform B-elimination? Explain your answer. CH,CH, CHs H,CH,C CH,CH, H,CH,C HCH,C CHCH CH,CH, HyCH;C CHCH CH;CH, CHCH, A B
- 1. Why does H2 not give an IR spectrum? 2. Explain why primary amines and unsubstituted amides have two NH stretching absorptions. 3. Why do anhydrides show two carbonyl peaks? 4. HCl is known to give addition reactions to carbon-carbon double bonds. Why is this behavior not observed in this reaction? 5. Predict the structure of the product expected from addition of molecular bromine to maleic acid.For the following reaction, what significant changes would be expected by IR absorptions, (ignoring C-H absorption): " a. NaNH2 b. CH;CHI a peak around 1710/cm would disappear a peak around 2150/cm would disappear a peak around 1710/cm would appear No change observed.7. Answer all parts of this question. The synthesis of the drug minoxidil is shown below. Minoxidil is a K+ channel opener and vasodilator used in the treatment of hair loss. CI NH2 POCI3 NH3 HN NH [6] CI CI [7] CI NH2 (13) (14) [8] MCPBA NH2 NH NH2 No N. NH2 [9] CI NH2 (15) Minoxidil (a) The synthesis of compound (13) is achieved using three molar equivalents of phosphoryl chloride. This reaction [6] proceeds via a mechanism similar to that seen in the Vilsmeier reaction. Provide a complete mechanism for the substitutions of all three oxygens. What is the driving force for this reaction [6]? NN 8.