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- (c) Reaction of acetanilide with bromine Br: CH3 (d) Hydrolysis of 4-bromo-2-chloroacetanilide with HCl and ethanol HCI CH,CH,OHWhat is the major organic product obtained from the following reaction? H HC A) 1 B) 2 HO H₂SO4 C) 3 OH 2 سل، ز. مل D) 4 OHAs far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?
- By reacting the following compound with one equivalent of HBr in acetonitrile at 40 ° C, the main organic products are:Hydrolysis of amides is an important reaction, because it represents the first step in the digestion of dietary protein. Which of the following compounds is formed as a result of the hydrolysis of N,N-diethylpropanamide as shown below? CH3CH2 N-CH2CH3 + H₂O CH2CH3 HCI OA) B) CH3CH2 NH2 HO N-CH2CH3 CH2CH3 H CH3CH2 NHCH2CH3 D)51. Which is NOT a valid resonance structure for the conjugate base of this molecule? (A) (C) S (A) OEt O :O: : OEt HBr ROOR OCH 3 (B) 52. What is the major product of this reaction sequence? O PPh3 (D) 11 Mg ether (B) de OEt :0 aom Сосно LOCH 3 53. Which reagent is necessary for this transformation? (D) H OEt H OEt CH31 PPh3 ACS 56.
- PQ-19. Which phosphorus reagent is required for this reaction? (A) PPh3 (B) PPh3 (C) H PPh3 (D) PPh3Rank the reactivity of the compounds below toward nucleophilic acyl substitution by writing the compounds' letters in the proper blanks in the box below. `NH CI Br CH3 CH3 A В C E rank compounds for acyl substitution reactivity most least reactive reactivePQ-20. This type of reaction, typical of carboxylic acids, esters, acid halides, anhydrides and amines, is called: (A) a bimolecular nucleophilic substitution. (C) an electrophilic substitution. (A) (A) H3C-C-OCH₂CH3 OH R CI PQ-21 What would be hydrolyzed most slowly with aqueous NaOH? lo (B) OH₂ (C) H3C-C-OCH₂CH3 H3C-C- H CI + H₂O (B) a nucleophilic addition. (D) a nucleophilic acyl substitution. (C) PQ-22. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of ethyl acetate, shown, in dilute aqueous acid? RiOH OH (D) H3C- (D) OH (B) H3C-C-OCH₂CH3 OH₂ + HCI si in
- Answer the following questions based on the information provided. (b) 1. SOCI2 OH 2. NaN3, heat 3. ELOH draw the products after the first and second step after 1st step after 2rd step ii) why does not the reaction afford the amine as final product? Explain it by drawing the mechanism of final step IZH₂C 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 заFollowing are structural formulas for amphetamine and methamphetamine. H NH, CH3 (a) (b) Amphetamine (racemic) Methamphetamine (racemic) The major central nervous system effects of amphetamine and amphetamine-like drugs are locomotor stimulation, euphoria and excitement, stereotyped behavior, and anorexia. Show how each drug can be synthesized by reductive amination of an ap- propriate aldehyde or ketone and amine.