1. Hydrocarbon Derivatives
Aldehydes, Ketones, Carboxylic Acids, & Esters

2. Functional Group #4
Aldehydes

3. Carbonyl Group >CO
Oxygen attached to a carbon by a double covalent bond.
Strong dipole

4. Aldehydes O General formula: RCH or RCHO
Carbonyl group is always at the end of the aldehyde (C on one side, H on the other).
Find the name of the alkane with the same # of carbons. Change the final e to -al.
Never need #’s for aldehydes – always at end. 

5. O H =
HCO H 
HCH H
Aldehyde comes from
Alcohol Dehydrogenated

6. HCH O 
Methanal
Common name = formaldehyde O H
HCCH 
Ethanal
= acetaldehyde
1 metabolic product of ethanol on its route to acetic acid.

7. Acetaldehyde Evidence that it is carcinogenic.
Natural component of many ripe fruits.
Contributes to odors of rosemary, daffodil, bitter orange, camphor, angelica, fennel, mustard, & peppermint.
A component of cigarette smoke.

8. Ends in CHO so it’s an aldehyde.
CH3CH2CH2CHO
4 Carbons so base name is butane.
Drop final -e and add –al  butanal.

9. Properties of Aldehydes- O R
H H R - -   +
C=O
C=O   + + H H
Aldehydes are polar! Bumps up the boiling point.
1-way Hydrogen bonding in H2O. Bumps up solubility.

10. Functional Group #5
Ketones

11. Ketones
Carbonyl group , >C=O, located within a C chain instead of at the end.
General Format:
R and R' may or may not be the same. O =
RCR'

12. Naming Ketones Nearly always have a number.
Take the corresponding alkane name.
Drop final –e.
Add –one.
Number in front gives location of >C=O. (Lowest possible #.)

13. H O H HCCCH H H 2-propanone Common name = acetone O =
CH3CH2CH2CCH3
2-pentanone

14. Aldehydes & Ketones Known for appealing tastes & smells.
Used as flavorings in food & candy.
Used as fragrances in perfumes.
Vanilla & cinnamon = aldehydes

15. Properties of Aldehydes & Ketones
Aldehydes & ketones contain C=O group, which makes the molecules polar.
Boiling point: Higher than alkanes, lower than alcohols.
In pure aldehydes & ketones, hydrogen bonding does NOT occur. No H bonded to O.
Can have 1-way Hydrogen bonding in water, so they are pretty soluble in H2O.

16. Functional Group #6
Carboxylic Acids

17. Carboxylic Acids Carboxylic Acids are electrolytes! O Acidic H+
General Formula = RCOH
Contains a carbonyl group & a hydroxyl group bonded to same C.
The H is acidic. It ionizes in water!
Carboxylic Acids are electrolytes! =

18. Ionization of Acetic Acid
CH3COOH + H2O  CH3COO- + H3O+

19. Table R O =
General Format: R-C-OH or R-COOH

20. Which of the following is an electrolyte?
CH3OH
CH3COOH
CH2O
C3H6O
alcohol
aldehyde
ketone
Correct answer is B, the carboxylic acid.

21. Which of the following is a nonelectrolyte?
HCl
CH3COOH
NaOH
CH3OH
Correct answer is D, an alcohol.

22. Naming Carboxylic Acids
Never need a number – functional group always at end.
Find name of corresponding hydrocarbon.
Drop final –e.
Add the ending –oic + the word acid.

23. O =
HCOH
1 C  methane.
Methanoic acid
Sting in red ants, bees O H
HCCOH =
Ethanoic Acid or
Acetic acid
2 C  ethane

24. CH3CH2CH2CH2COOH
5 C’s  pentane so the name is pentanoic acid.

25. Common carboxylic acids
Acetic acid – vinegar. Also produced in doughs leavened with a specific yeast  sourdough bread
Citric acid
Tannic acid
Ascorbic acid
Lactic acid
Poly(lactic acid) – biodegradable polymers used as sutures in internal surgery.

26. Properties of Carboxylic Acids
Contain –COOH group.
H is bonded to O. Hydrogen bonding occurs. Leads to increases in boiling point over corresponding alkane.
Also can form hydrogen bonds with water so the smaller acids are pretty soluble.

27. Functional Group #7
Esters

28. Esters O = General format: RCOR‘
R and R‘ = hydrocarbon branches. Can be the same or different.
Esters contain a carbonyl group and a bridge O, both in the middle of the chain.
Esters are POLAR, but NO H bonded to O however.

29. Esters O = RCOR‘ or RCOOR’
Combination of a carboxylic acid & an alcohol.
The carbonyl group and “R” come from the carboxylic acid.
The bridging O and the R’ come from the alcohol.

30. Esters Responsible for many distinctive odors Pineapple Banana Orange
Wintergreen

31. Naming Esters
Name the hydrocarbon branch bonded to the bridge O first. Branches end in –yl.
The base name is derived from the branch containing the carbonyl group. Count up all the C atoms in this branch, including the C in the carbonyl.
Find the hydrocarbon base name. Drop the final –e and add –oate.

32. O
So you name this branch 1st. =
CH3CH2COCH3
Carbonyl Group
Bridge O
Methyl Propanoate

33. Bridge O O =
CH3CH2CH2COCH2CH3
Name this branch 1st.
Ethyl Butanoate
Pineapple

34. Bridge O O =
CH3COCH2CH2CH2CH2CH3
Name this branch 1st.
Pentyl Ethanoate
Banana

35. O =
CH3OCCH2CH2CH3
Bridge O
Name this branch 1st.
4 C’s on the other side = but
Methyl butanoate - apple

36. O =
CH3CH2CH2CH2CH2CH2CH2CH2-O-C-CH3
Bridge O
Name this branch 1st.
2 C’s on the other side: ethane
Octyl Ethanoate orange