Chapter 38, Problem 2ASA

How would you prepare each of the following compounds using either an acetoacetic ester synthesis or a alonic ester synthesis? Show all intermediate structures and all reagents.[Three only] A. B. COOH OH C. D. 0 H2C CHCH2CH2CCH3

Fats and greases have mostly aliphatic regions which are hydrophobic. Provide a schematic of howsoaps/detergents remove fats and grease from the soiled material. * see image

What chemical has the common name "lye"? Pick one of the 3 esters and show the hydrolysis mechanism to make a carboxylic acid. The organic “R” should be used to limit the redrawing time of the entire molecule. * see image

Provide the products for each reaction. There are two and they are not related. *see image

d. a phenylal Give the major organic product(s) of each of the following reactions or sequences of reactions. Show all levant stereochemistry. [three only] 0 A. B. CH3 Bra CH3COOH OH 1. Br₂, PBrz 2 H₂O 12

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