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- In which compound is the halogen substituted most rapidly by aq hydroxide ions? a. CH3CH2CH2CH2Cl b. (CH3)3CI c. (CH3)3CCl d. CH3CH2CH2CH2I4. Predict the major organic product(s) of the following reactions. Be sure to clearly identify stereochemistry as appropriate. a. b. C. d. 1. BH3, THF 2. H₂O₂, NaOH Br CH₂12 1. Mg, THF 2. D₂0 Zn-Cu CH₂Cl2 Na DMFselect reagents: cyclopentanone Reagents a. C6H5CHO b. NaOH, ethanol c. Pyrrolidine, cat. Hj. d. H₂C=CHCN e. H3O+ f. LDA g. A) bg EtOC(=O)CO₂Et h. i. B) ka k. I. m. O: BrCH₂CH=CH₂ NatOEt, ethanol Br₂, H+ K+ t-BUO™ CH2(CO2Et)z heat C) jh CO₂Et D) Im
- For Nos. 63-70 Choose: A -if the indicated property/behavior in item I is greater than in item II B-if the indicated property/behavior in item I is less than in item II. C- if the indicated property/behavior is equal in item I and item II. D- if the indicated data is insufficient to make a comparison.6. Predict the product for the following reaction. "NH₂ Br H₂N NO₂ D. H₂O* A. Fe/HCI IV OH OH Br 11 NH₂ "NH₂ H₂N A. IB. II C. III D. IV E. V 7. Provide the reagents necessary to carry out the following reaction. NH₂ V 1. LIAIH4 2. H₂O NH₂ B. H₂CCOCI C. Br₂/FeBr3 E. dil. Na₂CO3 III7. Reaction Scheme. NH₂ NH2 or two differnet methods (no same steps/reagents) C5H12N2 1. xs Mel, xs K2CO3 2. Ag2O, H₂O 3. heat Br2, xs NaOH, xs H₂O OHC 1.03 2. DMS CHO
- 4. Provide the missing reagent(s) and major product(s) for the following reactions. a. a.ii. b. НО. A + B a.i. H₂SO4 (conc.), A pyridine a.iii. HO a.iv. CI OH A B6. 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 pyridine4. Draw the organic products formed in each of the following reactions. il b. C. 1₂ (excess) -OH CE .CO₂Et [1] LDA CHz(CO,Et)2 [2] CH₂CH₂Br [3] H₂O+, A [1] NaOEt [2] CH₂CH₂Br [1] NaOEt [2] CHSCH₂Cl (3) H₂O*, A d. 'OEI [1] NaOE1 [2] CH₂CH₂CH₂CH₂Br [3] H₂O*, A [1] LDA [2] CH₂CH₂Br
- 3 Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or name of the reaction as shown in the example. Starting Materials Ex. b. C. d. dj f. 09 ỌCH3 CH3 CH3 NO₂ Reagents H₂O H* (cat.) C1₂ AICI3 HNO3 H₂SO4 SO3 H₂SO4 Br₂ FeBr3 AICI3 Major Product(s) O= OH3. Stereochemistry. Predict the stereochemistry of the major product formed for each of the following reactions. Give an explanation for your choice. а. ÇHO SiMe3 A `OPMB MgBr2 • Et20 95% (20:1) b. a. MegAI, Cp2ZrCl2 (cat.) CICH2CH2CI B b. 70% Br, ZnCl2 (1 eq) Pd(0) (cat.) с. 1. CBr4, Ph3P, Zn 2а. п-BuLi (2.1 eq), hexane, THF 2b. H20 workup CHO 3. 56% BH, THE 4. Pd(PPH3)4 (cat.) NaOEt, toluene, 80 °C Br d. Me 2. TSOH• H20 (1.2 ec) TBSO. 1а. Ме2CuLi, Elyо D2 (bicyclic) 94% D1 1b. NC-CO2ME, HMPA 91% 1c. aq NH,CI workup toluene, refluxProvide the reagents. Но + enantiomer A 1. KOt-Bu, heat 2. mCPBA 3. MeMgBr 4. H2O B. 1. conc. H,SO4, heat 2. MCPBA 3. MeBr С. 1. РBгз 2. KOt-Bu 3. mCPBA 4. MeMgBr 5. H2O D. 1. Br2, hv 2. KOt-Bu 3. mCPBA 4. MeMgBr 5. H2O E. 1. Br2, hv 2. KOt-Bu 3. MCPBA 4. MeBr 5. H2O F. 1. Br2, FeBr3 2. KOt-Bu 3. mCPBA 4. MeMgBr 5. H2O G. 1. Br2, FeBr3 2. KOt-Bu 3. mCPBA 4. MeBr 5. H20