1. Name and draw structural formulas for the four carboxylic acids with the molecular formula C5H10O2. Which of these carboxylic acids are chiral?
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1 CHEM 122: Introduction to rganic Chemistry Chapter 10: Carboxylic Acids. 1. ame and draw structural formulas for the four carboxylic acids with the molecular formula C5H102. Which of these carboxylic acids are chiral? 2. Write the IUPAC name for each carboxylic acid. H CH HC CH H c) CCl3CH 3. Draw a structural formula for each carboxylic acid. 2-Aminopropanoic acid 3,5-Dinitrobenzoic acid c) Dichloroacetic acid d) o-aminobenzoic acid 4. Draw a structural formula for each salt. Sodium benzoate Lithium acetate c) Ammonium acetate d) Disodium adipate e) Sodium salicylate f) Calcium butanoate 5. Propanedioic (malonic) acid forms an intramolecular hydrogen bond in which the H of one CH group forms a hydrogen bond with an of the other CH group. Draw a structural formula to show this internal hydrogen bonding. (There are two possible answers.) 6. The following compounds have approximately the same molecular weight: propanoic acid, 1-butanol, and diethyl ether. Arrange them in order of increasing boiling point. 7. Arrange these compounds in order of increasing solubility in water: acetic acid, pentanoic acid, decanoic acid.
2 8. Complete the equations for these acid-base reactions. H ah C-a c) H CH HCl C C H d) CH ahc 3 9. Formic acid is one of the components responsible for the stinging of biting ants and is injected under the skin by bee and wasp stings. The pain can be relieved by rubbing the area of the sting with a paste of baking soda (ahc3) and water, which neutralizes the acid. Write an equation for this reaction. 10. The normal ph range for blood plasma is 7.35 to Under these conditions, would you expect the carboxyl group of lactic acid (pka 4.07) to exist primarily as a carboxyl group or as a carboxylate anion? Explain. 11. The pka of ascorbic acid is Would you expect ascorbic acid dissolved in blood plasma, ph , to exist primarily as ascorbic acid or as ascorbate anion? Explain. 12. Complete the equations for the following acid-base reactions. Assume one mole of HCl per mole of amino acid. CH3CHC - a H2 HCl (aq) CH3CHC - a H3 HCl (aq)
3 13. Complete these examples of Fischer esterification. In each case, assume an excess of the alcohol. CH H H CH H H CH C H H c) CH 14. From what carboxylic acid and alcohol is each ester derived? c) CH3CCH2CH2CCH3 d) 15. Methyl 2-hydroxybenzoate (methyl salicylate) has the odor of wintergreen. This compound is prepared by Fischer esterification of 2-hydroxybenzoic acid (salicylic acid) with methanol. Draw a structural formula for methyl 2- hydroxybenzoate.
4 16. Show how you could convert cinnamic acid to each compound. H H H trans-3-phenyl-2-propenoic acid (Cinnamic acid) C 17. Give the expected organic product formed with phenylacetic acid, C6H5CH2CH, is treated with each of the following reagents: ahc3, H2 ah, H2 c) H3, H2 d) LiAlH4 then H2 e) abh4 then H2 f) CH3H H2S4 (catalyst) g) H2/i 18. Procaine (its hydrochloride salt is marketed as ovocaine) was one of the first local anesthetics developed for infiltration and regional anesthesia. It is synthesized by the following Fischer esterification: H H Fischer esterification Procaine 4-Aminobenzoic acid 2-Diethylaminoethanol Draw the structural formula of Procaine. Which of the two nitrogen atoms in Procaine is the stronger base? c) Draw the structural formula of ovocaine (the hycrochloride salt of Procaine). d) Would you predict Procaine or ovocaine to be more soluble in blood?
5 19. Methylparaben and propylparaben are used as preservatives in foods, beverages, and cosmetics. Show how each of these preservatives can be prepared from 4- aminobenzoic acid. Methyl-4-Aminobenzoate (Methylparaben) H 4-Aminobenzoic acid Propyl-4-Aminobenzoate (Propylparaben) 20. When 5-hydroxypentanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw a structural formula for this lactone.
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Unit 2: Quantities in Chemistry
Mass, Moles, & Molar Mass Relative quantities of isotopes in a natural occurring element (%) E.g. Carbon has 2 isotopes C-12 and C-13. Of Carbon s two isotopes, there is 98.9% C-12 and 11.1% C-13. Find