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1
Organic Chemistry: the study of carbon containing compounds.
Prior to 1828, organic compounds can only be obtained from living organism until Fredrick Wohler prepared urea - chemical in urine (an organic compound)
NH4Cl + AgNCO → NH2-CO-NH2 + Ag
Now - the bulk of organic compounds are manufactured in the lab.
Clothes perfumes shoes athletic products foods
Makeup furniture computers televisions cars
Plastics CD dishes cups carpets linoleum etc
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EXCEPTIONS EXCEPTIONS
Inorganic compounds: containing carbon atoms
Oxides / like CO and CO2 are inorganic examples
Cyanides / like NaCN Mg(CN)2 are inorganic compounds
Carbonates /like Na2CO3 MgCO3 are inorganic compounds
Carbides / like SiC Al4C3 are inorganic compounds
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BOND CAPACITY OF ATOMSBOND CAPACITY OF ATOMS
H C O N F Cl Br I
C O N F Cl Br H
HYDROCARBONSGROUPS OF ORGANIC COMPOUNDS CONTAINING HYDROGEN AND CARBON
ALIPHATICS AROMATICS
Alkanes Alkenes Alkynes
Cyclic compounds
Have distinct cyclic carbon ring
Are not named for their Aroma
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HYDROCARBONSHYDROCARBONS
ALIPHATICS
C C
ALKANES ALKENES ALKYNES
SINGLEBONDS
DOUBLEBONDS
TRIPLEBONDS
CNH2N+2CNH2N
CNH2N-2
N – REPRESENTS C ATOMS
C C
AROMATICS
CONTAIN BENZENE RING
CYCLIC COMPOUNDS
C C
COLORLESS,FLAMMABLE LIQUID
SWEET AROMA
CARCINOGENIC EFFECT
AROMATICS MEAN THAT
- CONJUGATED RINGS OF CARBON
- UNSATURATED BONDS OF C
- RESONANT BONDS OF CARBON
I. Classes of Organic Compounds
Hydrocarbons (C & H only) Heteroatomic compounds
Aliphatic Aromatic *
Alkanes *
Alkenes *
Alkynes *
Cyclic compounds *
Alcohols *
ethers
aldehydes
ketones
Carboxylic acids *
Esters *
amines
amides
C C
C C
R OH
R O R'
R C
O
H
R C
O
R'
R C
O
OH
R C
O
OR'
R C
O
NH2
R NH2
benzene ring
C C
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What is the general formula of alkanes? (CnH2n + 2)
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BRANCHES - OFF PARENT CHAINBRANCHES - OFF PARENT CHAIN
ALL WILL APPEAR TO HAVE C AND H
THE BRANCHES WILL HAVE ONE LESS HYDROGEN AND ARE CALLED ALKYLS
METH - 1 ETH - 2 PROP - 3BUT - 4PENT - 5HEX - 6HEPT - 7OCT - 8NON - 9DEC - 10
METHYL - CH3
ETHYL - C2H5
PROPYL - C3H7
BUTYL - C4H9
PENTYL - C5H11
HEXYL - C6H13
HEPTYL - C7H15
AND SO ON !!
CH3 CH3-CH2
CH3-CH2-CH2
CH3-CH2-CH2-CH2
CH3-CH2-CH2-CH2-CH2
CH3-CH2-CH2-CH2-CH2-CH2
CH3-CH2-CH2-CH2-CH2-CH2-CH2
AND SO ON !!!!
PREFIX - C ALKYL FORMULA CONDENSED STRUCTURAL
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H
H C CH3 methyl H H H
H C C CH3-CH2 ethyl H H
Branches off parent chain Not part of the parent chain in a sequence
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Ways of presenting organic Ways of presenting organic compoundscompounds
Structure formula - shows connectivity of atoms in a compound
Molecular formula - indicate type and number of atoms C3H8
Condensed structural formula - shows connecting group of atoms in a compound
CH3 - CH2 - CH3
Line structural - shows hydrocarbons as lines with bends for carbon
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CH3
CH3-CH-CH3
methyl groups
CH3 CH3
CH3-CH-CH-CH3
CH2CH3
CH3-CH2-CH2-CH-CH2-CH3
Ethyl group
BRANCHES ARE NOT PART OF THE PARENT CHAIN !
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1. Find the longest continuous chain of carbon atoms. Assign this chain as the parent name .(# of carbon atoms)
2. Determine the groups attached to the parent chain
3. Assign attachment position of group to main chain by starting at end which gives lowest position number.
4. Identical groups attached to the main chain are designated with prefixes.
2-di, 3-tri, 4-tetra, 5-penta
5. Different groups attached to main chain are written in alphabetical order.
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CH3 (branch)
CH3-CH2-CH2-CH-CH2-CH3 (parent chain)
6 5 4 3 2 1
3-methylhexane
on third C CH3 six carbons (hex)
NUMBER FROM RIGHT TOLEFT – BRANCH CLOSEST TO THE RIGHT SIDE !!
CARBON NUMBER BRANCH PARENT CHAIN
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NOMENCLATURE OF ALKANESNOMENCLATURE OF ALKANES
1. CARBON NUMBER OF BRANCH IS FIRST
2. THERE MAY BE SIMILAR BRANCHES – PLACE ALL CARBON NUMBERS IN ORDER. Eg 2,2,3 - 3,4,5 - separated by commas followed by a hyphen
3. THE NAME OF THE BRANCHES MUST FOLLOW – IF THERE ARE MULTIPLE
BRANCHES YOU MUST ADD PRFIXES TO INDICATE HOW MANY… 2-DI 3 -TRI 4 -TETRA 5 - PENTA 6 - HEXA
4. THERE MAY BE DIFFERENT BRANCHES SO YOU MAY HAVE DIFFERENT ALKYL GROUPS AND CARBON NUMBERS…
3,3-diethyl-2,5,5-trimethyl (write down groups alphabetically – ignore prefix)
5. THE NAME OF THE PARENT CHAIN COMES LAST – ONE WORD
3,3- diethyl-2,5,5- trimethyloctane EASY !!
14
A. CH3 CH3
CH3CHCH2CHCH3
B. CH3 CH3
CH3CH2CHCH2CCH2CH3
CH3
2,4-dimethylpentane
3,3,5-trimethylheptane
15
Write a condensed structure for
A. 3,4-dimethylheptane
B. 2,2-dimethyloctane
16
A. 3,4-dimethylheptane CH3
CH3CH2CHCHCH2CH2CH3
CH3
2,2-dimethyloctane CH3
CH3CCH2CH2CH2CH2CH2CH3
CH3
SolutionSolution
Quiz
17
An alkane in which one or more H atoms is replaced with a halogen (F, Cl, Br, or I)
CH3Br 1-bromomethane
Br
CH3CH2CHCH3 2-bromobutane
Cl
chlorocyclobutane
18
List other attached atoms or group in alphabetical order.
Br = bromo, Cl = chloro
Cl Br
CH3CHCH2CHCH2CH2CH3
4-bromo-2-chloroheptane
19
The name of this compound is:
Cl CH3
CH3CH2CHCH2CHCH3
1) 2,4-dimethylhexane
2) 3-chloro-5-methylhexane
3) 4-chloro-2-methylhexane
20
CH2Cl2
CHI3
CBr4
CCl2F2
dichloromethane
triodomethane
tetrabromomethane
dichlorodifluoromethane
21
CH3Br
Cl
I
Br
bromomethane
2-chloropropane
iodocyclohexane
2-bromo-2,4-dimethylpentane
22
• Saturated compounds (alkanes) have the maximum number of hydrogen atoms attached to each carbon atom.
• Unsaturated compounds have fewer hydrogen atoms attached to the carbon chain than alkanes.
• Unsaturated compounds contain double or triple bonds
23
Alkene (CnH2n) 1. - ene suffix for alkenes 2. Main chain must include the double bond.3. position of double bond indicated by prefix numbering location.4. For multiple double bonds :
di = 2 double bondstri = 3 double bonds
Alkyne (CnH2n-2) 1. - yne suffix for alkynes2. Nomenclature rules are similar to that of alkenes
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When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the double or triple bond.
CH2=CHCH2CH3 1-butene
CH3CH=CHCH3 2-butene
CH3CCCH3 2-butyne
25
Write the IUPAC name for each of the following unsaturated compounds:
A. CH3CH2CCCH3
CH3
B. CH3C=CHCH3
2-pentyne
2-methyl-2-butene
26
• same general formula as alkenes
• structural isomers of alkenes
27
Name the following:
Br
Cl
Cl
bromocyclopentane
1,3-dichlorocyclohexane
28
Br
F
CH3
CH3
Cl
Cl
Cl
5-bromo-2-methylheptane
4-fluoro-1,2-dimethylcyclohexane
1,2,6-trichloro-4-ethyl-2-methylheptane
29
Same molecular formula
Same number and types of atoms
Different arrangement of atoms
30
The formula C4H10 has two different structures
CH3
CH3CH2CH2CH3 CH3CHCH3
butane 2-methylpropane
When a CH3 is used to form a branch, it makes a
new isomer of C4H10.
31
CH3CH2CH2CH2CH3 pentane
CH3
CH3CHCH2CH3 2-methylbutane
CH3
CH3CCH3 2,2-dimethylpropane
CH3
Write 3 isomers of C5H12 and name each.
32
Draw all of the constitutional isomers for the following. C4H9Cl
Cl
Cl
Cl
Cl
1-chlorobutane 2-chlorobutane 1-chloro-2-methylpropane
2-chloro-2-methylpropane
• unsaturated cyclic hydrocarbons
34
1. Monosubstituteda. group benzene
chlorobenzeneethylbenzene
b. special names:
phenol
2. Benzene as a group- phenyl
Cl CH2CH3
OH
35
A carbon compound that contain -OH (hydroxyl) group
CH4 methane
CH3OH methanol
CH3CH3 ethane
CH3CH2OH ethanol
36
IUPAC names for longer chains number the chain from the end nearest the -OH group.
CH3CH2CH2OH 1-propanol
OH CH3CHCH3 2-propanol
CH3 OH CH3CHCH2CH2CHCH3 5-methyl-2-hexanol
37
• Part of an organic molecule where chemical reactions take place.
• Composed of an atom or group of atoms.
• Replace a H in the corresponding alkane.
• Provide a way to classify organic compounds.
38
Name Suffix Group Example
Aliphatic ane,ene,yne C - C C4H10
Alcohol -ol R - OH CH3-OH
Ether -ether R - O - R´ CH3-O-CH3
Aldehydes -al R – C = O
H
Ketones -one R - C - R´
O
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Name Suffix Group Example
Carboxylic acid -oic acid R - C - OH
O
CH3COOH
Ester -ate R - C - O - R´
O
CH3COOCH3
Amine
Amide
-amine
-amide
R - N - R´
R´
R - C - N – R´
O R´
CH3NH2
CH3CONH2
40
Contain an -O- between two carbon groups
CH3-O-CH3 dimethyl ether
CH3-O-CH2CH3 ethyl methyl ether
41
Classify each as an alcohol (1), phenol (2), or an ether (3):
A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH
B. _____
OH
CH3
Learning CheckLearning Check
3
2
1
42
Functional Groups
CH3CH2CH2CO
H
aldehyde
CH3CH2CCH2CH3
O
ketone
43
In an aldehyde, an H atom is attached to a carbonyl group
O carbonyl group CH3-C-H
In a ketone, two carbon groups are attached to a carbonyl group
O carbonyl group CH3-C-CH3
Aldehydes and KetonesAldehydes and Ketones
44
O O
CH3 -C-CH3 CH3-C-CH2-CH3
propanone 2-butanone
Cyclohexanone
O
Naming KetonesNaming Ketones
45
Classify each as an aldehyde (1), ketone (2) or neither(3).
O
A. CH3CH2CCH3 B. CH3-O-CH3
CH3 O
C. CH3-C-CH2CH D.
CH3
O
Learning CheckLearning Check
2 3
21
46
Functional Groups
carboxylic acid
ester
CH3CHCH2CO
OH
CH3
CH3CH2CO
OCH2CH3
47
Functional groups
CCH
C
OCH
OH
O
C
C
O
OHO
alcohol alkene
ester
carboxylic acid
ketone
48
carboxylic acid
etherester
amine
aldehyde
CHCH2
CO OH
OCH
CH2C
N
NH2
C
O
OCH2
CO
H
49