1. ORGANIC CHEMISTRY Alkanes Alkenes Alkynes Ring Structures Cyclic
Functional
Groups
Chain Structures
Branches –
Substituents

2. TERMS ORGANIC CHEMISTRY carbon containing molecules HYDROCARBONS
carbon & hydrogen molecules

3. BONDING PATTERNS/REQUIREMENTS
Hydrogen (1) Nitrogen (3) Oxygen (2) Halogens (1) carbon (4)
X = F, Cl, Br, I N .. : O .. C H X .. : N +
Nitrogen Ion, N+, (4)

4. ORGANIC NOMENCLATURE “Carbon to Carbon” -- bond identification alkANE
Single bond between all carbon atoms pg 131
Fromula: CnH2n+2
alkENE
Double bond (at least 1) between carbon atoms
Formula: CnH2n
alkYNE
Triple bond (at least 1) between carbon atoms
Formula: CnH2n-2

5. # C’s
- ane
- ene
- yne 1
Methane
---- 2
Ethane
Ethene
Ethyne 3
Propane
Propene
Propyne 4
Butane
Butene
Butyne 5
Pentane
Pentene
Pentyne 6
Hexane
Hexene
Hexyne 7
Heptane
Heptene
Heptyne 8
Octane
Octene
Octyne 9
Nonane
Nonene
Nonyne 10
Decane
Decene
Decyne
If structure is a substituent (branch)
“yl” ending: methyl; butyl; hexyl

6. DRAWINGS Skeletal Condensed Line CH3 CH3CHCH3 Structural C H C C C H
H H H C
C C C

7. BASIC NAME PATTERN PREFIX --- PARENT -- SUFFIX # of substituent
Chain molecules
PREFIX --- PARENT -- SUFFIX
substituent
# of
carbons
Family
- ane
- ene
- yne

8. ORGANIC CHEMISTRY name ending single bond: -ane
double bond: -ene
triple bond: -yne
branch (substituent): -yl
R, R group: carbon chain
# C single bond double bond triple bond
methane
ethane ethene ethyne
propane propene propyne
butane butene butyne
5 & more, use prefix for number (5, pent-; 6, hex-; 7, hept-; etc)

9. NAMING HYDROCARBONS
1. Find longest continuous carbon chain -- Parent
2. Count from end closest to 1st branch -- Prefix
3. Family, base bond type -- Suffix
Prefix - Parent - Suffix
“-” dashes bet. # & name
“,” comma bet. numbers & name

10. 1 2 3 4 5
branch
methyl 1 2 3 4 5
branch
methyl
off of C#4
Parent: 5 C’s, pent
Family: single bonds,
Suffix; -ane
off of C#2
Prefix: branch, C#2
1C: methyl
2-Methylpentane

11. 1 2 3 4 5 6 7
Name: 5 1 2 3 4
=: double bond, functional group, needs to be named & identified where
Name:

12. Name:
Name:

13. If same branch occurs more than once in same molecule;
use 2-di, 3-tri, 4-tetra, etc.
name:

14. If same branch occurs more than once in same molecule;
use 2-di, 3-tri, 4-tetra, etc. 2 |
CH3
name:

15. O H 2 |
CH3
Name:

16. O 2 |
CH3
Name:

17. O HO
Name:

18. Name: OH
Name:
Name: OH

19. .. .. .. . . . . .. .. FUNCTIONAL GROUPS -ane -ene -yne Aromatic
Benzene Ring:
Arene
6 carbon ring w/ alt. dbl. bonds
Alcohol Ether Amine
CARBONYL; C=O
Aldehyde Ester Amide
R CH2 N .. ..
R CH2 O H
R CH2 O CH2 R ..
ending:
-ol ether amine
-al oate amide
R C H O
. .
R C C O C R O ..
. .
R C C NH2 .. O
. .

20. Ketone Carboxcylic Acid
R C C OH .. O
. .
R CH2 C CH2 R O
. .
ending:
-one oic acid
RINGS
single bonds
Multiple bonds
Name: cyclo-parent
cyclopentane
cyclopentene cyclopentyne

21. FUNCTIONAL GROUP SERIES
- OH
- O -
H - C = O
C = O
- COOH
- COO -
Ethers
Esters
Ketones
Carboxcyclic
Acids
Alcohols
Aldehydes

22. A B C Identify functional group present in each molecule displayed
1: Carboxcyclic Acid : Ester : Alcohol
4: Carbonyl - Ketone : Carbonyl - Aldehyde A
H H
H C C = O H B O
C C C C O
C C O C

23. D E F 1: Carboxcyclic Acid 2: Ester 3: Alcohol
4: Carbonyl - Ketone : Carbonyl - Aldehyde D
CH3 CH CH3 OH E O
C C C OH F O
C C C H

24. G H 1: Carboxcyclic Acid 2: Ester 3: Alcohol
4: Carbonyl - Ketone : Carbonyl - Aldehyde G O
CH3 C CH2 CH3 H O
C C C O C OH

25. FTIR -- InfraRed IR 1. Bet vis & microwave 2. Organic chemists
use cm-1
3. cm-1  E of vibration
No 2 cmpds give exact sample IR (enantimoers)
2 types of molecular vibration
stretching bending
3 vibrations
symmetrical asymmetrical scrissoring

26. Stretching Frequencies ()
C-C C-O C-N cm-1
C=C C=O C=N N=O
C C C N
C-H O-H N-H
2 imprt areas for prelim exam of spectra
fct group region fingerprint complex
Imprt for -OH NH C=O
strong bands aromatics (benzene ring)
strong out-of-plane bending & ring bending

27. C - H Stretch Alkanes 3000 - 2840(s) other: near 1375 & 1450
Cycloalkanes (m)
other: near 1450(m)
Alkenes above 3000(s)
other: near 1416(m); (w); near 850(s)
Alkynes (n,s) stronger-narrower than OH & NH
other: (b,s); (w,o)
Aromatics & (w,o)
other: (s); (m)
Aldehydes (2:s) w/ near 1390
other: near 2720(m)

28. C to C Alkanes below 500; 1200 - 800(w) are of little value
best is C-H
CH & 2872
CH2 near 2926 & near 2853 (+/-10)
CH near 1375 & near 1450
Alkenes (m)
Alkynes (w)

29. ALCOHOLS -- PHENOLS ETHERS Alkenes - Phenols -OH & C-O
OH (b,s); (m)
CO (s)
Ethers C-O-C
similar to C-C-C but more intense (s)
ETHERS
Ethers C-O-C
similar to C-C-C but more intense (s)

30. CARBONYL C=O containing
Carbonyls (ketones, aldehydes, carboxylic acids, esters, anhydrides, amides)
C=O (s)
Ketones (m)
Aldehydes
C-H (2:m) & near 2720(m)
Carboxylic Acids
O-H (b,s)
C=O near 1766(s)
C-O & O-H near (m) & near (m)
Esters
C=O (s) higher freq than ketones
C-O (2:s)

31. NITROGEN CONTAINING Amides NH2 or NH 1650 - 1515
other: near 3520(m) & near 3400(m)
C=O & 1650(s)
C-N near 1400(m)
Amine
NH near 3500(w) & near 3400(w)
other: NH (m)
C-N (m)
aromatic C-N (s)
Nitriles
CN (m)
Discuss Galvani & Volta 31

32. SUMMARY Alkanes, alkyl groups C-H 2850 – 2960 m – s
Alkenes =C-H – m
C=C – m
Alkynes C-H s
-CC – m
Alcohols O-H – s,b
C-O – s
Aromatics =C-H m
ring , s
Amines N-H – m
C-N , m
Carbonyl Cmpds C=O – s,b
Carboxylic Acids O-H – s,b
Nitriles CN – m
Nitro NO s
SUMMARY
spontaneous rxn = -G
this is a mathematic eqn
have discussed conditions that make G +/-
-G(exo) when -H(exo) & +S 32

33. N-H O-H C-H CN CC C=O C=N C=C Fingerprint Region % Transmittance
(cm-1)
% Transmittance
N-H
O-H
C-H
CN
CC
C=O
C=N
C=C
Fingerprint
Region

34. ALKENE % Transmittance 4000 3000 2000 1600 1200 1000 800 600 (cm-1)
(cm-1)
% Transmittance
Discuss Galvani & Volta 34

35. ALKYNE % Transmittance 4000 3000 2000 1600 1200 1000 800 600 (cm-1)
(cm-1)
% Transmittance
Discuss Galvani & Volta 35

36. ALCOHOL % Transmittance 4000 3000 2000 1600 1200 1000 800 600 (cm-1)
(cm-1)
% Transmittance
Discuss Galvani & Volta 36

37. Website for spectral information of molecules