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- A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.In the workup of the grignard reaction of turning bromobenzene to benzoic acid, we start by mixing the grignard with HCl and diethyl ether. We discard the aqueous layer and wash the organic layer with water. Then, the organic layer is extracted with NaOH. Then, the extracts are heated to remove ether. Then, it is precipitated with HCl. Precipitate collected. Let it dry and finally, purified with toluene and hexanes. Please make a flowchart of the process of this workup indicating what products and byproducts are forming. And what compounds are in the aqueous layer and organic layer in the steps.Propose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.
- For the reaction shown below, 582 mg of 4-chlorophenol, 798 mg of benzyl bromide, and excess sodium hydroxide are used to obtain 847 mg of 4-chlorophenyl benzyl ether. What is the percent yield of 4-chlorophenyl benzyl ether? 4-chlorophenol MW = 129 g/mol; benzyl bromide MW = 171 g/mol; sodium hydroxide MW = 40.0 g/mol; 4-chlorophenyl benzyl ether MW = 219 g/molReactions of Carboxylic Acids - Fisher esterification: Acid-catalyzed ester formation from carboxylic acid and alcohol OH H₂SO4 OH - Carboxylic acid: conversion to acyl halides: SOCI₂ RCO₂H + SOCI₂ (w/ pyridine) → RCOCI SOCI₂ CH3OH CH3COH Reactions of Amide NH₂ 1. LiAlH4 2. H₂OWhat is the theoretical yield of 4-(hydroxylmethyl)-2-methoxyphenol, if there is 2.6 mmol of vanillian acetate, 3.0 ml of 95% ethanol and 7.8 mmol of sodium borohydride used?
- Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.If ethanol was added to each of the following, which would be ineffective in preparing ethyl benzoate? Benzoyl chloride. Benzoic anhydride. Benzoic acid with catalytic sulfuric acid. Benzamide. What is the stereochemistry of this compound? 2E, 5E 2Z, 5Z 2Z, 5E 2E, 5ZThe base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
- Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each haloalkane with triphenylphosphine, (2) the phosphonium ylide formed by treatment of each phosphonium salt with butyllithium, and (3) the alkene formed by treatment of each phosphonium ylide with acetone.Write the Ky reactions for pyridine, for sodium 2-mercaptoethanol, and for cyanide. H+ binds to S in sodium 2-mercaptoethanol and to C in cyanide. (Hint: Spectator ions, which do not react in solution, appear on both sides of the reaction and can be removed.) N: HOCH.CHS: Na+ CN Pyridine Sodium 2-mercaptoethanol Cyanide Refer to the Ka values below for their conjugate acids. Which of the three bases shown above is the strongest? NH HOCH.CH.SH HCN Pyridinium ion K. = 6.3 x 10-6 2-Mercaptoethanol K. = 1.9 X 10-10 Hydrogen cyanide K = 6.2 x 10-10In the reaction of the phenol nitration, a mixture of o-nitrophenol and p-nitrophenol is formed. The melting point of nitrophenol is 45, the melting point of p-nitrophenol is 112 ° C. How would you interpret this difference depending on their molecular structure?