Download CH. 18 ACID -

ORGANIC CHEMISTRY
Alkanes
Alkenes
Cyclic
Structures
Alkynes
Ring Structures
Chain Structures
Branches –
Substituents
Functional
Groups
TERMS
ORGANIC CHEMISTRY
carbon containing molecules
HYDROCARBONS
carbon & hydrogen molecules
BONDING PATTERNS/REQUIREMENTS
Hydrogen (1)
Nitrogen (3)
Oxygen (2)
Halogens (1)
X = F, Cl, Br, I
carbon (4)
..
N
H
O
..
X
..
:
C
..
N
:
O
C
N
C
+
Nitrogen Ion, N+, (4)
N
C
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
# C’s
1
- ane
Methane
2
3
4
Ethane
Propane
Butane
Ethene
Propene
Butene
- yne
---Ethyne
Propyne
Butyne
5
Pentane
Pentene
Pentyne
6
Hexane
Hexene
Hexyne
7
Heptane
Heptene
Heptyne
8
Octane
Octene
Octyne
9
Nonane
Nonene
Nonyne
10
Decane
Decene
- ene
----
If structure is a substituent (branch)
“yl” ending: methyl; butyl; hexyl
Decyne
DRAWINGS
Condensed
Line
CH3
CH3CHCH3
Structural
Skeletal
H H H
H C C C H
C
H H H
C C C
BASIC NAME PATTERN
Chain molecules
PREFIX --- PARENT -- SUFFIX
substituent
# of
carbons
Family
-- ane
-- ene
-- yne
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
1
methane
2
ethane
ethene
ethyne
3
propane
propene
propyne
4
butane
butene
butyne
5 & more, use prefix for number (5, pent-; 6, hex-; 7, hept-; etc)
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
4
CH3
1CH
3
3
CH
2
CH2
CH2
5CH3
branch
methyl
off of C#4
5
3
2
CH3
CH
CH2
4
CH3
CH2
1
CH3
branch
methyl
off of C#2
2-Methylpentane
Parent: 5 C’s, pent
Family: single bonds,
Suffix; -ane
Prefix: branch, C#2
1C: methyl
1C
C7
C
C
C
2
3
C
C
C
4
6
5
Name:
C
C
1
C
2
C
3
C
4
C5
=: double bond, functional group, needs to be named & identified where
Name:
CH3
CH3
H2C
CH CH2
CH2
CH3
H2C
CH2
CH2
CH2
C
CH3
CH2
CH3
Name:
Name:
CH2
CH
CH3
If same branch occurs more than once in same molecule;
use 2-di, 3-tri, 4-tetra, etc.
CH3
H3C
CH
CH2
CH2
CH
CH3
name:
CH3
CH2
If same branch occurs more than once in same molecule;
use 2-di, 3-tri, 4-tetra, etc.
CH3
H3C
CH
CH2
CH2
CH
CH32
|
CH3
name:
CH3
CH2
CH3
O
H3C
H
CH
CH2
CH2
CH
CH32
|
CH3
Name:
CH3
CH2
H3C
CH2
O
CH3
CH2
CH
CH
CH23
|
CH3
Name:
CH3
CH2
CH3
O
H3C
HO
CH
CH2
CH2
CH
CH3
Name:
CH3
CH2
Name:
CH3
H3C
CH
CH2
CH2
Name:
CH
CH3
CH2
CH3
Name:
H3C
CH
CH2
CH2
CH3
CH
CH3
CH3
CH2
FUNCTIONAL GROUPS
-ane
-ene
-yne
Arene
Alcohol
..
R CH2 ..
O H
ending:
-ol
Aldehyde
..O ..
Aromatic
Benzene Ring: 6 carbon ring w/ alt. dbl. bonds
Ether
Amine
..
R CH2 O
.. CH2 R
ether
CARBONYL; C=O
Ester
..O..
..
R CH2 N
-amine
Amide
..O..
..
R C H
..
R C C O
.. C R
R C C NH2
-al
-oate
-amide
ending:
Ketone
..O..
R CH2 C CH2 R
ending: -one
Carboxcylic Acid
..O..
..
R C C OH
..
-oic acid
RINGS
single bonds
Name: cyclo-parent
cyclopentane
Multiple bonds
cyclopentene
cyclopentyne
FUNCTIONAL GROUP
SERIES
- OH
Ethers
-O-
Esters
H-C=O
Ketones
C=O
Carboxcyclic
Acids
- COOH
Alcohols
- COO Aldehydes
Identify functional group present in each molecule displayed
1: Carboxcyclic Acid
4: Carbonyl - Ketone
A
2: Ester
3: Alcohol
5: Carbonyl - Aldehyde
H H
H C C=O
H
B
C
O
C C O C
O
C C C
1: Carboxcyclic Acid
4: Carbonyl - Ketone
2: Ester
3: Alcohol
5: Carbonyl - Aldehyde
D CH CH CH
3
3
E
OH
F
O
C C C H
O
C C C OH
1: Carboxcyclic Acid
4: Carbonyl - Ketone
G
O
CH3 C CH2 CH3
2: Ester
3: Alcohol
5: Carbonyl - Aldehyde
H
O
C C C O C OH
FTIR -- InfraRed
IR
1. Bet vis & microwave
2. Organic chemists
use 4000 - 400 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
Stretching Frequencies ()
C-C C-O C-N
C=C C=O C=N N=O
C C CN
C-H O-H N-H
1300 - 1500 cm-1
1900 - 1500
2300 - 2000
3800 - 2700
2 imprt areas for prelim exam of spectra
4000 - 1300
900 - 650
1300 - 900
fct group region
fingerprint complex
Imprt for -OH
NH
C=O
strong bands 1600 - 1310 aromatics (benzene ring)
900 - 650 strong out-of-plane bending & ring bending
C - H Stretch
Alkanes 3000 - 2840(s)
other: near 1375 & 1450
Cycloalkanes 3100 - 2990(m)
other: near 1450(m)
Alkenes above 3000(s)
other: near 1416(m); 1000-650(w); near 850(s)
Alkynes 3333 - 3267(n,s) stronger-narrower than OH & NH
other: 700-610(b,s); 1370-1220(w,o)
Aromatics 3100 - 3000 & 2000 - 1650(w,o)
other: 900-675(s); 1300-1000(m)
Aldehydes 2830 - 2695(2:s) w/ near 1390
other: near 2720(m)
C to C
Alkanes below 500; 1200 - 800(w) are of little value
best is C-H
CH3 2962 & 2872
CH2 near 2926 & near 2853 (+/-10)
CH near 1375 & near 1450
Alkenes 1667 - 1640(m)
Alkynes 2260 - 2100(w)
ALCOHOLS -- PHENOLS
Alkenes - Phenols -OH & C-O
OH 3650 - 3584(b,s); 1420 - 1330(m)
CO 1260 - 1000(s)
Ethers C-O-C
similar to C-C-C but more intense 1150 - 1085(s)
ETHERS
Ethers C-O-C
similar to C-C-C but more intense 1150 - 1085(s)
CARBONYL
C=O containing
Carbonyls (ketones, aldehydes, carboxylic acids, esters, anhydrides, amides)
C=O 1870 - 1540(s)
Ketones 1300 - 1100(m)
Aldehydes 1740 - 1720
C-H 2830-2695(2:m) & near 2720(m)
Carboxylic Acids
O-H 3300 - 2500(b,s)
C=O near 1766(s)
C-O & O-H near 1320-1210(m) & near 1440-1395(m)
Esters
C=O 1750 - 1715(s) higher freq than ketones
C-O 1210- 1163(2:s)
NITROGEN CONTAINING
Amides
NH2 or NH 1650 - 1515
other: near 3520(m) & near 3400(m)
C=O 1694 & 1650(s)
C-N near 1400(m)
Amine
NH near 3500(w) & near 3400(w)
other: NH 1650-1580(m)
C-N 1250 - 1020(m)
aromatic C-N 1342-1266(s)
Nitriles
CN 2260 - 2222(m)
Alkanes, alkyl groups
C-H
2850 – 2960
Alkenes
=C-H
C=C
3020 – 3100
1640 – 1680
m
m
Alkynes
C-H
-CC-
3300
2100 – 2260
s
m
Alcohols
O-H
C-O
3400 – 3650
1050 – 1150
s,b
s
Aromatics
=C-H
3030
ring
1600, 1500
Amines
N-H
C-N
SUMMARY
m
s
3300 – 3500 m
1030, 1230
m
Carbonyl Cmpds C=O 1680 – 1750 s,b
Carboxylic Acids O-H 2500 – 3100 s,b
Nitriles
CN
2210 – 2260
m
Nitro
NO2
1540
s
m–s
% Transmittance
N-H
4000
C=O
Fingerprint
CN
O-H
C=N
Region
CC
C-H
3000
C=C
(cm-1)
2000
1600
1200 1000 800 600
% Transmittance
ALKENE
4000
3000
(cm-1)
2000
1600
1200 1000 800 600
% Transmittance
ALKYNE
4000
3000
(cm-1)
2000
1600
1200 1000 800 600
% Transmittance
ALCOHOL
4000
3000
(cm-1)
2000
1600
1200 1000 800 600
Website for spectral information of molecules
http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng