1. Chemistry 121 Winter 17
Introduction to Organic Chemistry and Biochemistry
Instructor Dr. Upali Siriwardane (Ph.D. Ohio State)
Office: 311 Carson Taylor Hall ; Phone: ;
Contact me trough if you have questions
December 16, 2016: Test 1 (Chapters 12-13)
January 23, 2017 : Test 2 (Chapters 14-16)
February 10, 2017 : Test 3 (Chapters 17-19)
February 22, 2017 : Test 4 (Chapters 20-22)
February 23, 2017: Make Up Exam: Chapters 12-22)

2. Chapter 16 and GHW#6 Questions
Carboxylic Acids, Esters, and Other Acid Derivatives

3. Chapter 16: Carboxylic Acids, Esters, and Other Acid Derivatives
16-1Structure of Carboxylic Acids and Their Derivatives Carbonyl Compounds and Acyl Compounds
16-2IUPAC Nomenclature for Carboxylic Acids
16-3Common Names for Carboxylic Acids Monocarboxylic Acids
16-4Polyfunctional Carboxylic Acids
16-5Physical Properties of Carboxylic Acids
16-6Preparation of Carboxylic Acids
16-7Acidity of Carboxylic Acids
16-8Carboxylic Acid Salts Uses for Carboxylic Acid Salts
16-9Carboxylic Acid Decarboxylation Reaction
16-10Structure of Esters
16-11Preparation of Esters Cyclic Esters (Lactones)
16-12Nomenclature for Esters
16-13Selected Common Esters
16-14Isomerism for Carboxylic Acids and Esters
16-15Physical Properties of Esters
16-16Chemical Reactions of Esters
16-17Sulfur Analogs of Esters
16-18Polyesters
16-19Acid Chlorides and Acid Anhydrides
16-20Esters and Anhydrides of Inorganic Acids

4. Bonding Characteristics of Carboxylic Acids
A carboxylic acid has functional a carboxyl group. A carboxyl group is a carbonyl group (C=O) with a hydroxo group (—OH) bonded to the carboxyl carbon atom.

5. Physical Properties of Carboxylic Acids
Both polar molecules and hydrogen bonding makes:
BP and MP are higher than alcohols ,
hydrocarbons and ether with comparable carbon numbers

6. Acidity

7. Physical Properties of carboxylic acids derivatives
Esters, amides, acid chlorides and acid anhydride have lower boiling and melting points than parent acid, Except Carboxylic Acid Salts

8. IUPAC Nomenclature of Carboxylic Acid and Esters
The IUPAC system deals with functional groups two different ways.
Modification of the hydrocarbon name to indicate the presence of a functional group.
Acid – R-COOH use -oic ending.
Esters –R-COOR’ use -oate ending.

9. Common Names of Carboxylic Acids

10. IUPAC Nomenclature of Carboxylic Acid and Esters

11. Carboxylic Acids

12. Esters as Flavors

13. Common/IUPAC Nomenclature of Esters

14. Nomenclature of Carboxylate salts
Metal alkanoate (-oate suffix for anion)
E.g. sodium salt of proponoic acid is
named as sodium proponate

15. Nomenclature of Acid Anhydrides
Alkanoic anhydride (-oic anhydride suffix)
E.g. anhydride of proponoic acid is named as proponoic anhydride
Mixed acid anhydride are name butanoic proponoic anhydirdes

16. 1. Identify the carboxylic acids, esters, amides and acid from the following and give their common and/or IUPAC names. Carboxylic Acids, Esters, and Other Acid Derivatives
a)Type:___________
Name:____________
b) Type:_________________
Name:__________________
c)Type:_________________
d)Type:___________
e)Type:_________________
f)Type:_________________

17. 1. Identify the carboxylic acids, esters, amides and acid from the following and give their common and/or IUPAC names. Carboxylic Acids, Esters, and Other Acid Derivatives g)
Type:________________
Name:__________________ h)
Type:___________________ i)

18. 2. Draw the condensed formula of following
carboxylic acid and their derivatives.
a) methyl propanoate
b) ethyl pentanoate
c) propanoyl chloride
d) N-methyl propanamide
e) N,N-dimethyl ethanamide
f) 2-methyl pentanamide
g) 2(a)-aminopropanoic
h) butanoic ethanoic anhydride

19. Polyfunctional Carboxylic Acids
Dicarboxylic acids
Oh my, such great apple pie!“
(oxalic, malonic, succinic, glutaric, adipic, pimelic)
"Metabolic" Acids
Propionic acid, (C3 mono acids): lactic, glyceric, and
pyruvic acids
Succinic acid (C4 diacid): fumaric, oxaloacetic, and malic acids
Glutaric acid (C5 diacid): a-ketoglutaric and citric acids

20. 3. Identify type and give name of each of the following poly functional carboxylic acids.
Type:______________Name:_____________ c)
Type:_______________
Name:______________ d)
Type:________________Nmee:_______________
e) Type:__________Name:__________ f)
Type:____________Name:___________

21. IUPAC:_______________ e) Common:___________
3. Give common/IUPAC names of following dicarboxylic acids. Use "Oh my, such great apple pie!" (oxalic, malonic, succinic, glutaric, adipic, pimelic).
a) Common:___________
IUPAC:_______________ b)
Common:___________ c)
Common:____________ d)
IUPAC:_____________
e) Common:___________

22. 3. Give common/IUPAC names of following dicarboxylic acids.
f) Name:______________
g) Name:__________
h)Common:__________
IUPAC:______________

23. Saturated Fatty Acids
Long chain even carbon atoms C >10

24. Unsaturated Fatty Acids
Long chain even carbon atoms with C=C bonds

25. 5. Give type/name of following fatty acids, and their derivatives.
CH3(CH2)10CO2H
Type:_______________
Name:______________
b) CH3(CH2)14CO2H
Type:________________
Name:_______________
c) CH3(CH2)16CO2H

26. d) CH3(CH2)7CH=CH(CH2)7CO2H
5. Give type/name of following fatty acids, and their derivatives.
d) CH3(CH2)7CH=CH(CH2)7CO2H
Type:________________
Name:_______________
e) f)
Type:________________ Name:________________
Type:_______________
Name:___________
d) H3(CH2)7CH=CH(CH2)7CO2H e)
Type:________________
Name:_______________ f)

27. Triglycerides: Triesters of glycerol

28. Preparation of Carboxylic Acids
Oxidation of primary alcohol to carboxylic acid (described in reactions of alcohols)
Tollen’s Oxidation using  basic Ag(NH3)2+ or
Bendict’s CuSO4/Na2CO2/Citrate
(described in reactions of aldehydes)
Oxidation of alkyl side chain of substituted aromatic hydrocarbons (reactions of aromatic alkyl compounds)
Hydrolysis of esters. (Described in this chaper)
Hydrolysis of acid, amides and cholrides etc.. )

29. Oxidation of Alcohols to Carboxylic Acids
Non-aromatic carboxylic acids: Oxidation of primary alcohols or aldehydes, using an oxidizing agent such as K2Cr2O7
Aromatic carboxylic acids: Oxidation of a carbon side chain (alkyl group) on a benzene derivative
Examples:

30. Oxidation of primary alcohols

31. Oxidation of Aldehydes
Tollen’s and Benedict’s
Oxidation of alkyl side chain substituted on a benzene ring

32. Chemical Reactions of Carboxylic Acids
Reduction to alcohols with reducing agents
(LiAlH4, NaBH4 etc.)
Reaction with halogen compounds to form acid chlorides(described below in preparation of acid chloride preparations)
Reaction with strong bases to form acid salts (described below in preparation of acid salts)
Reaction with strong alcohols to form esters (described below in preparation of esters)
Reaction with ammonia and amine compounds to form amides (described in amides chapter 17)

33. Carboxylic Acid Reduction: To alcohols

34. Acid chloride Formation

35. Preparation of esters. Esterification
acid alcohol > ester H2O

36. Amide Formation
(Cl)

37. 6) Name and complete following reactions1) 2) 3) 4)

38. 6) Name and complete following reactions5) 6)

39. Polyesters Polymers are formed by reacting difunctional monomers
Examples: dicarboxylic acids and dialcohols are used for the formation of polyesters
Two important polymers:
Poly(ethylene terephthalate) (PET)
Lactomer

40. Poly(ethylene terephthalate)
Poly(ethylene terephthalate) (PET): Prepared by reacting terephthalic acid (a diacid) and ethylene glycol (a dialcohol)
Used for making textiles and other plastic applications

41. Biodgradable Polymers
Lactomer: Used in surgical staples because of its biodgradable nature
It simply dissolves after several weeks and the by-products formed are lactic acid and glycolic acid both of which are part of human body

42. 7) Name and complete following reactions.
Condensation Polymerization
2) Aspirin synthesis

43. Cyclic Esters (Lactones)
Hydroxy acids contain both a hydroxyl and a carboxyl group and such compounds have the capacity to undergo intermolecular esterification to form cyclic esters
Takes place in situations where a five- or six-membered ring can be formed
Cyclic esters are called lactones 43

44. 7) Name and complete following reactions.
3) Cyclic ester formation
4) Decarboxylation of b- ketoacids

45. Fatty acids and Glycerides

46. 7) Name and complete following reactions.
5) Base hydrolysis of esters
6) Base hydrolysis of triglycerides

47. Base hydrolysis of triglycerides Saponification-Soap formation