C. 21.50 Rank the following compounds in terms of increasing acidity: Alpha Carbon Chemistry: Enols and Enolates OH 21.51 Draw the enol of each of the following compounds and identify whether the enol exhibits a significant presence at equilibrium. Explain. a. b. 요요 వి C.
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- Many common pharmaceuticals contain aromatic rings and complex structures; they are readily synthesized through the common reactions that you have beem studying From the following table of available reagents, choose how you would convert OH OH (Enter the letter of the chosen reagent; only a single reagent is necessary for this step.) Reagents available a. epichlorohydrin, base f.H, A b. (CH,),CNH; g. PhMgBr then H,0 c. (CH, ), CHNH, h. BnMgBr then H,0* d. BnCl, pyridune LH. (CH,)2C=0 (Previous Ac,0 j.H, H,CO17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen23. (30) Predict the major organic product of each reaction or provide the reagents needed to complete each transformation. AICI3 HO, CI (a) FeCla , Cl2 (b) Br2 (c) CH3 FeBr3 1. Cl2 , FeCl3 (d) 2. HNO3, H2SO4 1. HNO3, H2SO4 (e) 2. Br2, FeBr3 1. Cl2 , FeCl3 (f) 1. 2. Mg , ether 2. H20, H* (g) Hg, Zn, HCI -C-CH CI AICI3 H2 Pd 1000 psi (h-i) CI CI 1 equivalent (1) O,N. CH3S K* SO3 (k-I) C-CH3 AICI3 H2SO4 2. excess NH2NH2 КОн Na CH3CH2 CH2CH3 (m-n) KMNO4 NH3 excess CH2CH3 Page 6 of 6
- Q 16.23: The following reaction will produce a(n) H RCO₂H A ether. B carboxylic acid. C ester. D lactone. A B C D Give detailed Solution with explanation needed of all options..don't give Handwritten answersynthesize each from benzene and sketch the following: H-NMR; C-NMR; MS, and IR for the compounds: 1. ortho form of aminophenol 2. meta form of salicylic acidOEt 17.6 Give the product. 1. CH3MgBr (2 eq) 2. H3O*
- 28. The following compounds undergo electrophilic aromatic substitution EXCEPT A. I and II B. III and IV C. II and III D. III I. II. 29. Which alkene is the most stable? A. I B. II C. III D. IV III. II. III. IV. IV. 30. In the hydrohalogenation reaction of 1-phenylpropene, only 1-chloro-1-phenylpropane is obtained because A. a more stable carbonium ion is generated from this product. B. a more stable radical intermediate is generated from this product. C. a more stable benzene ring is generated from this product. D. a less stable transition state is generated from this product.32. (14) Predict the major organic product of the following reactions or provide the reagents needed to complete each transformation. Clearly show stereochemistry where appropriate. (a-b) (c-d) (e-f) (g-h) KOH heat LDA heat CH3 1. Br₂, light 2. CH3O+K, heat CH3 NaBH4 CH3OH Br S Na+ CN H₂O cold KMnO4 1. CH3MgBr 2. H₂O, H+22:43 10. Provide the following: the resonance structure of the intermediate that can resonate into the other intermediate that is given the product that results from the given resonance structure Specify which product is the kinetic product and which is the thermodynamic product . OH 50% H₂SO4 H~
- (13) A B C OD What is not an elementary step in the mechanism for the following reaction? H₂O НО. (A) loss of iodide to generate a carbocation (B) 1,2-methyl shift/rearrangement (C) nucleophilic attack by water (D) proton transfer D. You selected this answer.Write balanced chemical equations for the following reactions with proper chemical formulae and IUPAC names of the reactant and products and the conditions of the reaction for; i. ii. iii. iv. V. Hydrolysis of methyl propionate. Aldol condensation of ethanal. Oxidation of methyl ethyl ketone by copper ions. Synthesis of Ethylene glycol from ethylene. Dehydration of butanol.32. (14) Predict the major organic product of the following reactions or provide the reagents needed to complete each transformation. Clearly show stereochemistry where appropriate. (a-b) (c-d) (e-f) (g-h) (i-j) (m-n) KOH heat NBS hv 1. Br₂, light 2. CH3O+K, heat LDA heat CH3 NaBH4 CH3OH CH3 CH₂l2, Cu Zn H₂O „H Br Na+ CN H₂O cold KMnO4 1. CH3MgBr 2. H₂O, H+ CH3OH, heat CH3S- +Na acetone mCPBA