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- Which reaction sequence will most successfully generate the product shown below (1) HNO 3/H2SO4 (A) (2) KMNO4, H* , H20 (3) SnCl2/HCI (1) KMNO4, H* , H2O (B) (2) HNO-/H,SO, (3) SnCh/HC [?] HOOC. NH2 (1) HNO3/H2SO4 (C) (2) SnCl/HCI (3) KMNO4, H*, H2O (1) SnCh/HCI (D) (2) KMnO H. HO (3) HNO/H,SO4 4+ Sequence B Sequence D Sequence C Sequence AB) Please draw the mechanism of formation for ONE of the functional groups. excess C6H₂O₂ IR = 1720 cm-1 ¹H-NMR 2.65 (s. 8H) HO _OH H* catalyst C10H1604 ¹H-NMR 3.8 (s, 8H) 1.75 (s, 8H)How many acid-base steps occur in this mechanism? :OH fö OH ₂ H CI: -H₂O (C5H12O) (CsH3O*) :CI: :CI:- yox (C5H1*) (C5H₁1CI)
- 2. Draw the complete reaction mechanism for the following transformation and explain the observed results. EDCI DMAP G=& CHCI 3, 65 °C 78% yield HO₂C TBSO,,, HO₂C HO EDCI DMAP CHCI3, 65 °C N=C=N EDCI Et TBSO... no reaction(A) moose the correct product. 1. NaGE, Ero 2. H₂0, A 食。 CO₂ Et -CO₂E7 (B) Coret 31. Choose the best reagents. & 4 (A) 1. LAH; H₂0 2. CHz | 3. H₂0/H+ (B) 1. NaOH, -78% 2. CH31 3. H₂0/H (C) 1. LDA, -78%℃ 2. CH31 3. H₂₂0/H+ 1. Nah, 0°C 2. CH31 3. H₂2₂0/H+* (<) Colt (D)a. b. C. d. E. 3) Give the mechanism но O LOH 0 1.) Brz, H₂0 2) NaOH 1.) NaH 2) Br HOS xs HIS 0 2 •SH N₂UH, Brz H ₂0 |
- .2 Indicate if the following is likely to go through a S1 or SN2 mechanism. a) NaCI, H20 H3C-I H,C-CI 9) OCH, OCH, b) NaCN ČN h) Br Br Nal c) KBr to Br NaBr, DMSO Br LiBr, DMSO Br j) OH-, H,0 он e) Nal, CH3OH Br k) Br OH f) H20 HBr Br H20(iii) Explain why nucleophilicity in SN2 reactions varies in the following order: MeO > Pho™ > MeCOO.Which reagent(s) would be applied to carry out the following synthesis with minimum side products? 1) Br2, hv 2) xs NANH,, NH3, H,O 3) CH,(CH,),Br AICI, B) A) C) 1) AICI, D) 1) Raney Nickle 2) Br 2) Zn (Hg), HCI, heat
- (a) Provide a detailed mechanism for the reaction below. Explain any selectivity issues that arise. Ms = ---S -Me OMS CI + PhMgBr .CI19 Ⓒ) (Care.) 50.3 /H₂ SO4( Oxer) .... ? ← defeck 1₂.0+ / heat B 1 which of the following hatides will not work as electrophile in a Friedel - crafts altylation reaction ? Br Br (1) 1 # Br Jor T TE NWhich conditions will produce the target product in the highest yield? O A) 1. BH3; 2. H₂O₂, NaOH, H₂O B) 1. OsO; 2. S(CH3)2 C) 1. Hg(OAc)₂, H₂O; 2. NaBH4 D) H₂SO4, H₂O A ? B OH racemic mixture