1. State all the products formed from Hofmann elimination of the following amine. Choose the major product. Show the mechanism to obtain the major product. а. b. с. NH, CH,CHCH3 NH2 NH2
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- Give the major organic product(s) for each step of the following reactions: H2 NaCN В HCI/H20 SOCI2 ►E HBr A a) Lindlar 1. NaOH, д -D 2. H* CH3CH2OH 1, 2 eq CH3CH2M9B A- В H30* 2. Hзо* LDA - C b) 1. ВНз/THF HBr 1. C 2. H30* A Mg В Et,0 D 2. H2O2, OH", H20 c)An acetal produces the following three compounds upon hydrolysis. Of acetals A-E which could it be? H3CO OCH3 П A B U D Acetal A H2O H₂SO4(cat.) замен поста "OCH3 В + HO. H₂CO ОН D + OCH3 CH3OH E OCH3 "OCH3Predict the major product of the reaction. starting material O А. B. D. Е. OH OH 1. BH3 2. NaOH, H. H2O ОН OH H OH enol intermediate product
- Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr MeO B. H₂SO4, H₂O, HgSO4 E. Na2Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR I. TsCl, py Meo I₁, N Me Galanthamine OH3. Provide mechanisms for the following reactions. OH a. 18OH b. C. HO H₂180 cat. H H₂O -C=N: cat. H* 180 →EtOH + CH3CH₂CH₂CO₂H cat. CH3SO3H NHH₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br за
- What is the major organic product obtained from the following sequence of reactions? A. HNO3, H₂SO4 CEN NO₂ B. H₂, Pd/C CN NO₂ Na₂Cr₂O7 H₂SO4 CN D COOH CN 1. NaNO₂, HCI 2. CUCN E CN NO₂3B Complete the reactions below. OH NaBr/H₂SO4 D Mg Et₂O E (2 ισοδ) 1. HCOOEt Et₂O 2. H₂O/H* FBelow is a structure of Levonorgestrel (Plan B®), used in prevention of pregancy. но HH H. Levonorgestrel Plan B® Below is one of the reactions used in the synthesis. What type of reaction is it? он :CEC-H Lc=c-H THF as solvent Levonorgestrel H,CO H,CO O A grignard reaction. Nucleophilic acyl substitution. O Nucleophilic addition. O An SN2 reaction. O O
- Propose a synthesis of the topical anesthetic cyclomethycaine from 4-hydroxybenzoic acid, 2-methylpiperidine, and any other necessary reagents. HN' + HO. НО Cyclomethycaine 4-Hydroxybenzoic acid 2-MethylpiperidineWhat is the best set of reagents to achieve deoxygenation of 2-pentanone to pentane? A. NaClO2/NaH2PO4 B. LiAlH4, Et2O C. DIBAL-H, THF D. NH2NH2/t-BuOK, DMSOAn unsaturated ketone is converted to the 3-cyano derivative shown below. Which reagent could be used to accomplish this? CEN O 1. HCN (hydrogen cyanide) O 2. Methylmagnesium bromide followed by ammonia. O 3. Dimethylcopper lithium followed by sodium amide. O 4. Methylamine followed by a dehydrating agent like P205-