1. Rank the alanes below in order of increasing relative Lewis acidity (1 is most acidic, 4 is least acidic). Provide a brief explanation for your ordering. AlCl3 Al(Et)3 Rank: AICI(Et)2 AlCl2(Et)

Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.

(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?

Treatment of indene with NaNH2 forms its conjugate base in a Brønsted–Lowry acid–base reaction. Draw all reasonable resonance structures forindene's conjugate base, and explain why the pKa of indene is lower thanthe pKa of most hydrocarbons.

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?

The pKa, of the conjugate acid of morpholine is 8.33. (a) Calculate the ratio of morpholine to morpholinium ion in aqueous solution at pH 7.0. (b) At what pH are the concentrations of morpholine and morpholinium ion equal?

The gas-phase basicity of triphenylamine (876.4 kJ mol-1) is less thanthat of triphenylphosphine (940.4 kJ mol-1). Write an equation torepresent each reaction. Do you expect electronic or steric factors tocontribute more to this difference? Explain

Rank the molecules in decreasing (strongest to weakest) acidity. Include resonance structures if necessary and explain reasoning for rank.

Rank the following in order of decreasing basicity and explain why (based on their structures). hydroxide ion, ethoxide ion, phenoxide ion, and carboxylate ion

26. Rank the following compounds in order of increasing water solubility. The first compound in should have the lowest water solubility. OH 3 (a) 1<3<2 (b) 3 <2<1 (c) 2<1<3 (d) 3 <1<2