instructor_supplement_20 - Instructor Supplemental...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 20 The Chemistry of Carboxylic Acids Solutions to In-Text Problems 20.1 (b) (d) (f) (h) 20.2 (b) 9-Methyldecanoic acid (common: v -methylcapric acid). Note that the term v ( omega , the last letter of the Greek alphabet) is used in common nomenclature for a branch at the end of a carbon chain. (d) 2,4-Dichlorobenzoic acid (f) Cyclopropanecarboxylic acid 20.5 The NMR data indicate a para -substituted benzoic acid derivative; given this deduction, the para substituent must be a chlorine. 20.8 Extract an ether solution of the two compounds with an aqueous solution of NaHCO 3 , Na 2 CO 3 , or NaOH. The acid will ionize and its conjugate-base anion will dissolve in the aqueous layer as the sodium salt; p -bromotoluene will remain in the ether layer. After isolating the aqueous layer, acidify it with concentrated HCl; neutral p -bromobenzoic acid will precipitate. 20.9 (a) 20.10 (a)
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 20 2 20.11 (a) Follow the reverse of the steps shown in Eqs. 20.18a–c, text pp. 966–967, with R— = Ph—. (b) To favor ester hydrolysis rather than ester formation, use a large excess of water as solvent rather than an alcohol. By Le Châtelier’s principle, this drives the carboxylic acid–ester equilibrium toward the carboxylic acid. 20.13 (b) (d) 20.15 (b) 20.16 (b) 20.18 (b) 20.19 (b) On heating, 2,3-dimethylbutanedioic acid forms a cyclic anhydride containing a five-membered ring. Because a cyclic anhydride of a -methylmalonic acid would contain a very strained four-membered ring, it is not formed on heating.
Background image of page 2
INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 20 3 20.20 (b) 1,4-Benzenedicarboxylic acid (terephthalic acid) is a compound with the formula C 8 H 6 O 4 that gives the indicated diol on treatment with LiAlH 4 followed by protonolysis. 20.21 (a) This synthesis requires the addition of one carbon. Follow the general scheme in Study Problem 20.2, text p. 975. 20.22 (b) The compound decarboxylates; it is a disubstituted malonic acid in which the two a substituents are joined within a ring. The net effect is the replacement of the carboxy group by a hydrogen. 20.23 The following b -keto acids (and their enantiomers) will decarboxylate to give 2-methylcyclohexanone:
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 20 4 Solutions to Additional Problems 20.26 (a) (b) (c) (d) 20.28 (b) First, calculate the number of millimoles of succinic acid (see Table 20.1, text p. 950) in 100 mg of succinic acid: mmol succinic acid = 100 mg succinic acid 118.10 mg succinic acid (mmol succinic acid)
Background image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/30/2011 for the course MCMP 205 taught by Professor Staff during the Spring '08 term at Purdue University-West Lafayette.

Page1 / 10

instructor_supplement_20 - Instructor Supplemental...

This preview shows document pages 1 - 5. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online