1. Part 2: Functional Groups
Organic Chemistry
Part 2:
Functional Groups

2. Functional Groups Added to a H-C chain
in place of a H
at terminal C
in between carbons
Determine unique chemical & physical properties
Examples of functional groups
alkyls & halogens
hydroxyl group
alcohols
aldehyde group
carboxyl group
Organic acids
Ketones
Ether / Esters
Amine / Amide

4. Alcohols
Functional group simply replaces one or more H in the H-C chain
R - OH
hydroxyl group
not bases
not hydroxide polyatomic ion
Hydroxyl group forms a covalent bond with a carbon atom
a.k.a. non-electrolyte
In bases the OH- forms an ionic bond with a + cation and will ionize
a.k.a. electrolyte

5. Monohydroxy Alcohols Only one OH group Primary alcohols
-OH group is bonded to a C that is bonded to 1 other C.
Secondary alcohols
-OH group is bonded to a C that is bonded to 2 other Cs
Tertiary alcohols
-OH group is bonded to a C that is bonded to 3 other Cs

6. Structural formula, name and molecular formula?
CH3OH
CH3CH2OH
CH3CHOHCH3
COHCH3CH3CH3

7. Dihydroxy alcohols Alcohols that contain 2 hydroxyl groups CH2OHCH2OH
structural formula?
molecular formula?
name?
1, 2 - ethanediol
Common name - ethylene glycol
antifreeze

8. Trihydroxy alcohols 3 hydroxyl groups per molecule CH2OHCHOHCH2OH
structural formula?
molecular formula?
Name?
1, 2, 3 - propanetriol
common name = glycerol / glycerine
Alcohols with 3 OH
groups end in triol

9. Structural formula, name and molecular formula?
CH2OHCHOHCH3
CH2OHCH2CH2COHOHCH3
Structural formula & name?
CHBrOHCHCH3CHBrOH

10. Aldehydes Aldehyde group is found at end of H-C chain H C O
no number is needed to designate the aldehyde it is ALWAYS the #1 Carbon
R - CHO
aldehyde name ends in -al
Ex.
Formaldehyde
Methanal H C O

11. You can add alkyl groups and halogens to an aldehyde, but remember the C=O is always the number one carbon.
CH3CHCH3CH2CH2CHO
Always #1

12. Structural Formulas & Names
HCHO
CH3CH2CHO
CH3CH3CH3CCHO
CHBrBrCHO

13. Molecular Formula of Aldehydes
When writing the molecular formula count all C’s & H’s together and keep the functional group separate
They will all end in CHO
Ex. c.s.f. = CH3CH2CH2CHO
molec. f. = C3H7CHO

14. Ketones O C Functional group found in middle of H-C chain R - CO - R’
ketone names end in - one
Ex.
Acetone
Propanone
Used as solvents O C

15. Ketones Methanone Ethanone Propanone 2- Butanone 2- Pentanone
Don’t exist
Ethanone
Propanone
2- Butanone
2- Pentanone

16. Naming ketones O C Designate where the functional group
and side chains
are located with
lowest
possible number given to the functional group O C

17. Practice 2-methyl-3-pentanone 3,3-dimethyl-2-butanone
4-methyl-3-hexanone
5,5-dibromo-4-methyl-3-hexanone

18. Ethers O naming ethers name R groups in alphabetical order
ALKYL groups
Ethers
Functional group found inside H-C chain
R - O - R’ O
naming ethers
name R groups in alphabetical order
put spaces between alkyl groups and add “ether” as your ending

19. Structural formula & name?
diethyl ether
a.k.a. Ether
CH3OCH3
CH3CH2OCH2CH3
Molecular formula? C2H5OC2H5
CH3OCH2CH3
Molecular formula? CH3OC2H5
CH3CH2CH2OCH2CH2CH2CH3
Molecular formula? C3H7OC4H9

20. Carboxylic Acids O C O H naming
Functional group found at end of H-C chain
R - COOH
carboxyl group O C
O H
naming
drop “e” of alkane name and add - oic acid

21. Structural formula & name
CHOOH
methanoic acid
A.k.a. formic acid
CH3COOH
ethanoic acid
A.k.a. acetic acid
CH3CH2COOH

22. 6,6,7-trichloro-4-methylheptanoic acid
More complex naming
If the H-C chain contains halogen substitutions and methyl side chains number your carbons from the functional group
H - C - C - C - C - C - C - C
Cl Cl H C H H O
H Cl H H H H OH
| | | | | |
H H H 1

23. Properties of Carboxylic Acids
Weak ionization in water
H C
H O C
H OH
H C
H O C
H O-
water +
H2O +
H3O+
hydronium ion
ethanoic acid
acetic acid
acetate ion
Organic acids are weak electrolytes

24. Properties . . . . #2 Solubility of R-COOH if R = C1 - C3
As carboxylic acid
H-C chains increase
solubility decreases. #2
Properties
Solubility of R-COOH
if R = C1 - C3
completely miscible (soluble)
if R = C4 - C5
somewhat miscible (3.7g in 100g H2O)
if R > C5
completely immiscible (insoluble)
fatty acids

25. Properties . . . . #3 H C H O C H OH + + NaOH HOH NaCH3COO water
Organic acids react with bases to produce salts
neutralization
H C
H O C
H OH
water +
NaOH
HOH +
NaCH3COO
sodium hydroxide
sodium acetate
(salt)
ethanoic acid
acetic acid

26. Esters & Esterification
Slow, reversible dehydration process
organic acid reacts with an alcohol
Products are an ester and water
ester
water
alcohol
acid

27. Esters have sweet fruity odors
Functional Group
R - COO - R’
R groups are
alkyl groups
Esters have sweet fruity odors

28. ACID Naming Esters Alcohol 1. Name the R group bonded to the -O
2. Name the R group bonded to the = O drop the e (of the alkane name)
add -oate
ACID

29. Organic Reactions X + O2  CO2 + H2O
Combustion
Burning
H-Cs in the presence of O2 (g) will burn to produce CO2 and H2O
X + O2  CO2 + H2O

30. Law of Conservation of Matter
Substitution
When one or more hydrogen atoms of a H-C chain is replaced by a halogen.
C2H6 + Cl2  C2H5Cl + HCl
C2H6 + Cl2  C2H4Cl2 + H2

31. Addition Involves breaking a multiple bond
Unsaturated compounds become more saturated
Alkyne becomes an alkene
Alkene becomes an alkane
C2H2 + Br2  C2H2Br2
C2H4 + Br2  C2H4Br2

32. Polymerization
The process of bonding many small molecules (monomers) together to make a very long chain (polymer)
Water must be a product
Examples of polymers
starches
Proteins
nylon

33. Esterification Reaction
ethyl ethanoate
Ethanoic acid
ethanol
water

34. Structural formula & Naming
CHOOCH3
What were the alcohol and the acid?
CH3COOCH3
What were the alcohol and the acid?
CH3COOCH2CH3
alcohol and acid?
CH3CH2COOCH2CH2CH2CH3

35. Esterification must be done in the presence of a catalyst to make
the reaction go faster
Because Esterification deals
with organic MOLECULES the reaction is slow

36. Esterification resembles Neutralization
Double Replacement Reactions
Esterification resembles Neutralization
Reactants
Alcohol
Carboxylic acid
Products
Ester
Water
Ions not involved
Slow reaction
needs a catalyst
Reactants
Acid (Org or inOrg)
Base
Products
Salt
Water
Ions
Fast reaction
No catalyst

37. Amines First functional group to contain Nitrogen
N can only make 3 bonds
It has a total of 5 valence electrons
3 are unpaired

38. Naming Amines Drop the e from the parent chain name and add amine
You must number your carbons to show where the amine group is located
methanamine

39. Amides
Functional group containing a Nitrogen AND a carbonyl group (C=O) at the end of the chain
Carbonyl is always the #1 carbon
Drop the e from the parent chain name and add - amide
butanamide

40. Looooong carboxylic acid
Soap
Metallic salt of a higher carboxylic acid
Contains Na+ or K+
Looooong carboxylic acid
~ C12 - C 18
Most common soap
sodium salt of stearic acid
CH3(CH)16COONa

41. Saponification soap Reactants fat or oil Products trihydroxy alcohol
ester
strong base
NaOH
KOH
Products
trihydroxy alcohol
1,2,3-propanetriol
a.k.a. glycerol
soap
sodium stearate

42. Saponification Reaction
(C17H35COO)3C3H5 + 3NaOH 
C3H5(OH)3 + 3C17H35COONa
Sodium soap = bar soap
Potassium soap = liquid

43. Hard water ex. Ca2+ Mg2+ Fe2+ Hard water contains metallic ions
When soap is used in hard water the stearate ion combines with these ions and forms a greasy precipitate
soap scum

44. How do soaps clean? Soaps are ionic compounds and will ionize
Na+ and CH3(CH2)16COO-
Charged end is
hydrophillic
“water loving”
Non-polar end is
hydrophobic
“water hating”

45. Greece Grease H2O H2O H2O H2O H2O H2O H2O H2O H2O H2O H2O H2O H2O H2O

46. Animated Soap micelle

47. Advanced Isomers Isomers Same molecular composition
Same number of C, H, and/or O
Different structural formula
Different chemical properties
reactivity
Different physical properties
Melting point, boiling point, vapor pressure, evaporation rate, solubility

48. The End