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- 2. Provide a mechanism for the following transformation: OH H3O + CO2H₂C 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 за2. Provide a mechanism for the following transformation: OH O ملی OH H3O Δ لا + CO2
- 5A Explain which of the following statements are true and which are false. i. N,N'-dicyclohexylurea (DCU) is the dehydrating reagent that converts a carboxylic acid to the corresponding anhydride. ii. The fact that carbonyl compounds have a lower boiling point than alcohols with the same C atoms is because the molecular dipole moment of carbonyl compounds is less than that of alcohols. iii. 3-Methylbut-2-en-2-ol is the only tautomeric structure of 3- methylbutan-2-one.Q1/ Arrange and give reason the following sets of compounds in order of: 1) Increasing acidity H₂C CH₂ Ph OCH₂CH3 OCH₂CH OCH₂CH3 пазон наззакон показзають иззати 46 WASAAmantadine is effective in preventing infections caused by the influenza A virus and in treating established illnesses. It is thought to block a late stage in the assembly of the virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in sulfuric acid to give N-adamantylacetamide, which is then converted to amantadine. CH,C=N in H,SO, Br NHCCH3 NH2 1-Bromoadamantane Amantadine (a) Propose a mechanism for the transformation in Step 1. (b) Describe experimental conditions to bring about Step 2.
- N Ph :0: CH3 Primary amines add to aldehydes and ketones to give imines. Imines are formed in a reversible, acid-catalyzed process that begins with nucleophilic addition of the primary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolamine. Protonation of the hydroxyl group converts it into a good leaving group and an E1-like loss of water yields an iminium ion. Deprotonation yields the product imine and regenerates the acid catalyst. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 NH₂OH NH₂OH Ph- :0: OH CH3 CH3 361. There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppmThe reaction of methylpropene with HBr, under radical conditions, gives two intermediates. Propose a mechanism for the formation of the two products. Propose a mechanism for the following reaction and use electronic factors to account for the formation of a major product: CH2 CH2Br N-Bromosuccinimide (NBS) ho, CCI4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures o account for its stability.
- 5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.There are several isomeric alcohols and ethers of molecular formula C5H12O. Propose a structure for the isomer. Isomer B: δ = 0.92 (t, 7.8 Hz, 3 H), 1.20 (s, 6H), 1.49 (q, 7.8 Hz, 2H), 1.85 (s, 1H) ppmWhich of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4