Chapter 29, Problem 20P

2

Show how the following conversions might be accomplished. Show all reagents and all intermediate ructures. More than one step may be required [2 ONLY]: A. B. ° C. OH 0 OH 0

A 20.3 mL sample of 0.263 M triethylamine, (C2H5)3N, is titrated with 0.252 M hydrochloric acid. (1) At the titration midpoint, the pH is . (2) At the equivalence point, the pH is .

d. 3,4,5-trimethoxybenzoyl chloride . What is the order of decreasing reactivity towards nucleophilic acyl substitution for the arboxylic acid derivatives? (most reactive first) A. B. 0 0 O 0 0 H3C-C-O-C-CH3 H3C-C-N(CH3)2 H3C-C-OCH 3 (CH3)2CH-C-OCH3 I || ။ IV a. I, II, III, IV b. I, III, IV, II C. II, IV, III, I d. II, I, III, IV 0 0 0 0 0 R-C-O C-R R-C-NH2 R-C OR R-C-CI a. I, III, II, IV | 11 III IV b. II, III, I, IV c. III, II, I, IV d. IV, I, III, II

B. d. a hydrate 4. Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry [4 ONLY]. A. CH₂OH PCC CH2Cl2 0 H KCN HCN 2

Propose a synthesis of the anti-inflammatory drug Ibuprofen from benzene. Show all reagents and all intermediate structures. Assume that ortho and para isomers can be separated. (CH3)2CHCH2 CH3 CHCOOH 1buprofen be required

Assuming that no equilibria other than dissolution are involved, calculate the molar solubility of each of the following from its solubility product: (a) KHC4H4O6

Answer the following by equation  1. reactio of CH3MgBr with Acetone [CH3COCH3] 2. acetal formation reaction of acetaldehyde [CH3CHO] 3. preparation of ethylmethylether [C2H5OCH3]  4. the acidity of the carboxylic acid depends and affected by the substitutions on the rest of the acid molecule: draw 2 structures of acids to show the different effects on acidity by different subs

Consider the reaction sequence below to answer the following questions: 0 0 0 0 0 1. NaOEt, EtOH H3O* OEt OET 2 PhCH Br heat Ph + EtOH + CO₂ CHh B C A A. The starting material A in this reaction sequence is called a a. ẞ-keto ester b. a-carboethoxy ketone C. malonic ester d. acetoacetic ester B. Conversion of A into B is a type of reaction termed a. an acylation b. an enolation C. d. an alkylation a phenylation f reactions