5 Ethanal, CH₂CHO, can be converted by a two-step synthesis into 2-hydroxypropanoic acid. OH O H₂C- H O H 2-hydroxypropanoic acid (1) The reagents and conditions are 1st step 2nd step NaOH(aq), heat under reflux A Na₂Cr₂O, and dilute H₂SO4 heat under reflux B Cl₂, UV light NaOH(aq), heat und reflux CLIAIH in dry ether CO₂, room temperature D HCN, in presence of KCN(aq) dilute HCl(aq), heat under reflux

2. provide appropriate reagents

a) Write out the first 3 steps only(to the tetrahedral intermediate shown) in the 6-step arrow pushing mechanism showing how ethyl propanoate is hydrolyzed in acid to form propanoic acidand ethanol. b) NaOH/H2O also serveto hydrolyze an ester; briefly explain why NaOH/H2Ois generally preferable.

Give the balanced equation of acetylene and the following reactions • Combustion  • dilute KMnO4 • Ammoniacal CuCl / Ammonical AgNO3

Benzoic acid, Ph-COOH (C6H5CO2H), is not soluble in water while it dissolves in ether (diethyl ether), (CH3CH2)2O. Yet upon treatment with sodium hydroxide, benzoic acid turns hydrophilic and dissolves in water.  Provide chemical explanation of this observation.

The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?

The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a compound. A weighed amount of the compound is heated with concentrated HI, ether cleavage occurs, and the iodomethane product is distilled off and passed into an alcohol solution of AgNO3, where it reacts to form a precipitate of silver iodide. The Agl is then collected and weighed, and the percentage of methoxyl groups in the sample is thereby determined. For example, 1.06 g of vanillin, the material responsible for the characteristic odor of vanilla, yields 1.60 g of Agl. If vanillin has a molecular weight of 152, how many methoxyl groups does it contain?

As 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?

When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.

Write the formula of reagents used in the following reactions:(i) Bromination of phenol to 2,4,6-tribromophenol(ii) Hydroboration of propene and then oxidation to propanol.(b) Arrange the following compound groups in the increasing order of their property indicated:(i) p-nitrophenol, ethanol, phenol (acidic character)(ii) Propanol, Propane, Propanal (boiling point)