N,N-Diethyl-m-toluamide (DEET) is the active ingredient in several common insect repellents. Propose a synthesis for DEET from 3-methylbenzoic acid. H3C. H3C, HO `NE12 3-Methylbenzoic acid (m-Toluic acid) N,N-Diethyl-m-toluamide (DEET)
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- Starting with benzene, what is a possible product of this series of reactions?: 1) HNO3 & H2SO4 2) Fe, HCl 3) (CH3)2CH-Br, FeBr3 4) NaNO2, HCl, 0-10 oC 5) HBF4 2-fluoro-3-isopropylaniline m-fluoro-benzenesulfonic acid o-fluoro-isopropylbenzene 2-amino-benzenesulfonic acidWhen certain aromatic compounds are treated with formaldehyde (CH2O), and HCl, the CH2Cl group is introduced onto the ring. This reaction is known as chloromethylation. (a) Propose a mechanism for this example of chloromethylation. (b) The product of this chloromethylation can be converted to piperonal, which is used in perfumery and in artificial cherry and vanilla flavors. How might the CH2Cl group of the chloromethylation product be converted to a CHO group?Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390–3400):
- A carboxylic acid is formed when an a-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for thefollowing Favorskii reaction. (Hint: In the first step, HO- removes a proton from the a-carbon that is not bonded to Br; a three-membered ring is formedin the second step; and HO- is a nucleophile in the third step.)Phenol plus 1) 1/2 I2, HNO3; 2) Br2 + AlCl3; 3) HNO3/H2SO4; can yield ___________. 2-bromo-6-iodo-4-nitrophenol 1-bromo-3-iodo-4-amino-phenol 3-bromo-5-iodo-4-nitrobenzene 2-bromo-3-iodo-4-hydroxy-aniline 2-bromo-3-iodo-4-nitrophenolScheme 1: Reagents: (a) acetic anhydride, sulfamic acid, 60°C,30min,91%; (b) Et3SiH,I2,0-5°C,30min,82%. 1) Draw the FULL, ARROW-PUSHING MECHANISM 2) Provide a verbalization of the mechanism for your reaction mechanism 3) What is happening at each step? What atom is nucleophilic? Which atom is electrophilic? Which bonds are made? Which bonds are broken? 4) Imagine you are trying to describe the reaction mechanism and I can't see your display - how would you describe the mechanism in a way that I know, that you know, what you are talking about.
- i) 3-methyloctane-2,3-diol 11) 3-chloro-4-ethoxy-2-methylcyclopentanamine iii) N, N, 3,3-tetramethylbutan-2-amine iv) 1-ethoxy-2,5-difluorohexan-3-ol 6) 5-isopropoxy-3-isopropyl-6-propoxy-4-propylcyclohexane -1, 2-diol draw of the following names in skeletal formsgas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagent.(b) Bleach (sodium hypochlorite, NaOCl, a strong oxidizing agent) neutralizes and inactivates mustard gas. Bleach is also effective on organic stains because it oxidizes coloredcompounds to colorless compounds. Propose products that might be formed by thereaction of mustard gas with bleach.A carboxylic acid is formed when an a-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction. (Hint: In the first step, HO- removes a proton from the a-carbon that is not bonded to Br; a three-membered ring is formed in the second step; and HO- is a nucleophile in the third step.)
- The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)Which of the following reactions will not produce a carboxylic acid? Benzaldehyde + hot, conc'd KMnO4 1) Ph-N2+ + KI 2) BrMgCH=CH2 in ether, followed by H3O+ sec-butylBenzene + hot, conc'd KMnO4 1) Benzene, HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2; 4) CuCN; 5) dilute acid and heat 1) Benzene and acetyl chloride & AlCl3; 2) HCl & Ni Thank you!From 10 to 14. can i get an explanation on how to choose the appropriate products for these reactions? thank you
