Based on this retrosynthetic analysis, propose a synthesis of the anticoagulant (a substance that inhibits blood clotting) diphenadione. OEt OEt Diphenadione Diethyl phthalate Because of its anticoagulant activity for blood, this compound is used as a rodenticide.
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- Amobarbital is a sedative marketed under the trade name Amytal. Propose a synthesis of amobarbital, using diethyl malonate and urea as two of the starting materials.The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Show how this same synthetic strategy can be used to prepare ethosuximide and methsuximide.Show how to synthesize the following amines from the indicated starting materials byreductive amination.(a) benzylmethylamine from benzaldehyde
- Show how you would use appropriate acyl chlorides and amines to synthesize thefollowing amides.(a) N,N-dimethylacetamide (b) acetanilide (PhNHCOCH3)(c) cyclohexanecarboxamide (d)The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides.Show how these techniques can be used to accomplish the following syntheses.(a) benzoic acid S benzylamine (b) benzaldehyde S benzylamine(c) pyrrolidine S N@ethylpyrrolidine (d) cyclohexanone S N@cyclohexylpyrrolidine(e) HOOC¬(CH2)3 ¬COOH S pentane@1,5@diamine (cadaverine)Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions.(a) allyl bromide S allylamine (b) ethylbenzene S p@ethylaniline
- Show how Gabriel syntheses are used to prepare the following amines.(a) benzylamineWhich combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?Primary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the synthesis of a primaryamine using an alkyl halide and ammonia?
- When acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?+ ELOČOET H2N EtO + ELOH Reactions of a primary or secondary amine with diethyl carbonate under controlled conditions gives a carbamic ester. Write a detailed mechanism for this reaction (shown above) which proceeds in 4 steps, including proton transfer steps. Then draw Intermediate 3 in the window provided. The mechanism is detailed as follows: Step 1: Nucleophilic attack to yield zwitterion intermediate 1. Step 2: Protonation/deprotonation (i.e. "proton transfer") of zwitterion 1 to yield intermediate 2. Step 3: Intramolecular collapse of tetrahedral center in intermediate 2 to yield charged intermediate 3. Step 4: Deprotonation of intermediate 3 to yield neutral product. You do not have to consider stereochemistry. In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na",I', in your answer. Do not draw organic or inorganic by-products. PSynthesis of amides from acid chlorides is an effective tool for creating many different compounds. One such compound is DEET, a.k.a. (N,N)-Diethyl-m-toluamide, a powerful insect repellent. Propose a chemical synthesis of DEET from m-toluic acid and any other necessary reagents. Provide a literature reference for any reaction that is not common knowledge.