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- Like acid chlorides, acid anhydrides react with alcohols in the presence of pyridine to form esters. For the following reaction : (a) Draw a circle around the nucleophile ; (b) Draw a square around the electrophile; (c) Put a star next to the base; (d) Draw the structure of the tetrahedral intermediate in the box below. Then draw a reasonable 3-step arrow pushing mechanism for the reaction.Why does the carbomethoxy group directs the reaction to positions that are meta to it ?b) Why the formation of dinitrobenzaote is substantially disfavored ?c) Would you expect small amounts of the ortho and para substituted product ? How would you remove them if they are formed ?d) Why does water have a retarding effect on the nitration ?e) Explain why Benzene has lower reactivity in electrophilic addition reactions than cyclohexene?In the reaction of a nitrile with a Grignard reagent, there are two steps: a) nucleophilic addition of the Grignard to form an imine ion and b) hydrolysis of the imine to form a ketone. Draw the intermediate and the final product in this reaction. Ignore inorganic byproducts. 1. CH₂MgBr 2. H3O* Draw Imine Ion Intermediate 1. H30¹ 2. Neutralizing work-up a
- 2. Like acid chlorides, acid anhydrides react with alcohols in the presence of pyridine to form esters. For the following reaction: (a) Draw a circle around the nucleophile; (b) Draw a square around the electrophile; (c) Put a star next to the base; (d) Draw the structure of the tetrahedral intermediate in the box below. Then draw a reasonable 3-step arrow pushing mechanism for the reaction. pyridine + но Structure of tetrahedral intermediate Mechanism:4. In the following compound: (a). Circle the good leaving group. (b). Explain why it is a good leaving group. HO,In a William Ether Synthesis of Phenacetin experiment, the organic layer is washed twice with 5% aq. NaOH. The purpose of this step was to remove any unreacted acetaminophen from the organic layer by extracting it into the aqueous layer. 2. a) What reaction is occurring between acetaminophen and NaOH? Draw the reaction, mechanism, and product of this reaction step.
- a) Put these three common types of carbonyl compound in order of decreasing reactivity ester amide acid chloride b) For the least reactive, show the interconversion to its other resonance form: How does this electron delocalisation make it stable? c) For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?20:24 1 : 10. Draw the full cleavage of 2-ethoxypropane by HCI scheme on your paper, and then draw in the curved arrows for each step of the mechanism. HICI co OⓇ ← H₂O 11. What reagent can be used to convert 2-methylbutan-1-ol into 2-methylbutanal? A) Bleach B) LIAIH4 C) DMSO, (COCI)2, TEA D) Na₂Cr₂O7, H₂SO4 E) 03 12. Fill in the box with the major organic product of the first step of the reaction shown? H-Cl Send a chat O4. Draw the proper products for the following acid/base reaction, with diisopropylamide (1) acting as a base, and cyclohexanone (II) acting as an acid in the forward direction. II
- Draw the structure of the product obtained when this amine is treated with excess iodomethane and then heated with Ag0 (Hoffman elimination) ball & stick labels • Consider EZ stereochemistry of alkenes. • Draw only the elimination product, do not the leaving group. • In cases where there is more than one answer, just draw one. ChemDoodleDesign a synthetic pathway for the following transformation. Provide the reagents and products for each step. More than one step is required. OH ОН .... НОNitroalkanes are about as acidic as ketones and aldehydes. Nitroalkanes can also be utilized in reactions similar to the Aldol reaction (a reaction termed a Henry reaction). a) Rationalize why nitroalkanes are more acidic than alkanes. b) Provide a mechanism for both steps of the following Aldol-like (Henry) reaction. base conjugate base base less stable conjugate base NO2 (b) NO2 но NO2 - H20 H. H. кон O=Z