organic chemistry
DESCRIPTION
ORGANIC CHEMISTRY. Alkanes. Alkenes. Alkynes. Ring Structures. Functional Groups. Cyclic Structures. Chain Structures. Branches – Substituents. TERMS. ORGANIC CHEMISTRY. carbon containing molecules. HYDROCARBONS. carbon & hydrogen molecules. N. H. .. :. O. X. N. C. - PowerPoint PPT PresentationTRANSCRIPT
ORGANIC CHEMISTRY
Alkanes
Alkenes Alkynes
CyclicStructures
Functional Groups
Ring Structures
Branches –Substituents
Chain Structures
TERMS
HYDROCARBONS
ORGANIC CHEMISTRY
carbon containing molecules
carbon & hydrogen molecules
BONDING PATTERNS/REQUIREMENTSBONDING PATTERNS/REQUIREMENTS
Hydrogen (1) Nitrogen (3) Oxygen (2) Halogens (1) carbon (4) X = F, Cl, Br, I
H N..
N..
N:
O.. ..
O..
..
X ..: ..
C
C
C
C
Nitrogen Ion, N+, (4) N+
ORGANIC NOMENCLATURE
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
“Carbon to Carbon” -- bond identification
Formula: CnH2n-2
# C’s - ane - ene - yne
If structure is a substituent (branch)“yl” ending: methyl; butyl; hexyl
DRAWINGS
Line
Structural
Condensed
Skeletal
PREFIX --- PARENT -- SUFFIX
substituent # ofcarbons Family
-- ane-- ene-- yne
BASIC NAME PATTERNChain molecules
ORGANIC CHEMISTRY
name endingname endingsingle bond: -anedouble bond: -enetriple bond: -ynebranch (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 -- Parent2. Count from end closest to 1st branch -- Prefix3. Family, base bond type -- Suffix
Prefix - Parent - Suffix
“-” dashes bet. # & name
“,” comma bet. numbers & name
CH3
CHCH3 CH2 CH2
CH31
234
5
1
2 3 4
5
branchmethyl
off of C#4 CH3
CHCH3 CH2 CH2
CH3branchmethyl
off of C#2
Parent: 5 C’s, pent
Family: single bonds, Suffix; -anePrefix: branch, C#2 1C: methyl
2-Methylpentane
C
C C C C C
CC1
2 3 4 5 6
7
Name:
C C
C
C CC1 2 3 4 5
=: double bond, functional group, needs to be named & identified where
Name:
CH3
C CH2
CH
H2
CH2 CH3
CH2CH2
CH3
Name:
H2C
CH3
CH2
CH2CH2
CH3
C CH CH3
Name:
If same branch occurs more than once in same molecule; use 2-di, 3-tri, 4-tetra, etc.
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3
name:
If same branch occurs more than once in same molecule; use 2-di, 3-tri, 4-tetra, etc.
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3|CH3
name:
2
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3|CH3
Name:
H
O
2
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3|CH3
Name:
O
2
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3
Name:
O
HO
Name:
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3
OH
Name:
CH2
H3C CH2CH
CHCH2
CH3
CH3
CH3
OH
Name:
FUNCTIONAL GROUPS-ane -ene -yne
AromaticBenzene Ring:
Arene6 carbon ring w/ alt. dbl. bonds
Alcohol Ether Amine
CARBONYL; C=OAldehyde Ester Amide
ending:
ending:
-ol ether -amine
-al -oate -amide
..R CH2 O H.. R CH2 O CH2 R
..
..R CH2 N
..
R C H
O. .. .
R C C O C R
O
..
... .. .
R C C NH2
..O. .. .
Ketone Carboxcylic Acid
ending: -one -oic acid
R CH2 C CH2 R
O. .. .R C C OH
..
..
O. .. .
RINGS
single bonds
Name: cyclo-parent cyclopentane
Multiple bonds
cyclopentene cyclopentyne
FUNCTIONAL GROUP SERIES
- OH
- O -
H - C = O
C = O
- COOH
- COO -
Ethers
Esters
Ketones
Carboxcyclic Acids
Alcohols
Aldehydes
Identify functional group present in each molecule displayed
1: Carboxcyclic Acid 2: Ester 3: Alcohol 4: Carbonyl - Ketone 5: Carbonyl - Aldehyde
B OC C C
C OC C O C
A H H H C C = O H
1: Carboxcyclic Acid 2: Ester 3: Alcohol 4: Carbonyl - Ketone 5: Carbonyl - Aldehyde
E OC C C OH
F OC C C H
D CH3 CH CH3
OH
1: Carboxcyclic Acid 2: Ester 3: Alcohol 4: Carbonyl - Ketone 5: Carbonyl - Aldehyde
G OCH3 C CH2 CH3
H OC C C O C OH
FTIR -- InfraRed
IR1. Bet vis & microwave2. 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 1300 - 1500 cm-1
C=C C=O C=N N=O 1900 - 1500C C C N 2300 - 2000C-H O-H N-H 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=Ostrong 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 & 1450Cycloalkanes 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)
SUMMARY
Alkanes, alkyl groups C-H 2850 – 2960 m – s
Alkenes =C-H 3020 – 3100 m C=C 1640 – 1680 m
Alkynes C-H 3300 s -CC- 2100 – 2260 m
Alcohols O-H 3400 – 3650 s,b C-O 1050 – 1150 s
Aromatics =C-H 3030 m ring 1600, 1500 s
Amines N-H 3300 – 3500 m C-N 1030, 1230 m
Carbonyl Cmpds C=O 1680 – 1750 s,bCarboxylic Acids O-H 2500 – 3100 s,bNitriles CN 2210 – 2260 mNitro NO2 1540 s
N-H
O-H
C-H
CN
CC
C=O
C=N
C=C
Fingerprint
Region
4000 3000 2000 1600 1200 1000 800 600
(cm-1)
% T
rans
mitt
ance
ALKENE
4000 3000 2000 1600 1200 1000 800 600
(cm-1)
% T
rans
mitt
ance
ALKYNE
4000 3000 2000 1600 1200 1000 800 600
(cm-1)
% T
rans
mitt
ance
ALCOHOL
Website for spectral information of molecules
http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng