1 organic chemistry: the study of carbon containing compounds. prior to 1828, organic compounds can...

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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 !!

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A. CH3 CH3

CH3CHCH2CHCH3

B. CH3 CH3

CH3CH2CHCH2CCH2CH3

CH3

2,4-dimethylpentane

3,3,5-trimethylheptane

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Write a condensed structure for

A. 3,4-dimethylheptane

B. 2,2-dimethyloctane

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A. 3,4-dimethylheptane CH3

CH3CH2CHCHCH2CH2CH3

CH3

2,2-dimethyloctane CH3

CH3CCH2CH2CH2CH2CH2CH3

CH3

SolutionSolution

Quiz

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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

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List other attached atoms or group in alphabetical order.

Br = bromo, Cl = chloro

Cl Br

CH3CHCH2CHCH2CH2CH3

4-bromo-2-chloroheptane

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The name of this compound is:

Cl CH3

CH3CH2CHCH2CHCH3

1) 2,4-dimethylhexane

2) 3-chloro-5-methylhexane

3) 4-chloro-2-methylhexane

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CH2Cl2

CHI3

CBr4

CCl2F2

dichloromethane

triodomethane

tetrabromomethane

dichlorodifluoromethane

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CH3Br

Cl

I

Br

bromomethane

2-chloropropane

iodocyclohexane

2-bromo-2,4-dimethylpentane

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• 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

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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

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Write the IUPAC name for each of the following unsaturated compounds:

A. CH3CH2CCCH3

CH3

B. CH3C=CHCH3

2-pentyne

2-methyl-2-butene

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• same general formula as alkenes

• structural isomers of alkenes

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Name the following:

Br

Cl

Cl

bromocyclopentane

1,3-dichlorocyclohexane

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Br

F

CH3

CH3

Cl

Cl

Cl

5-bromo-2-methylheptane

4-fluoro-1,2-dimethylcyclohexane

1,2,6-trichloro-4-ethyl-2-methylheptane

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Same molecular formula

Same number and types of atoms

Different arrangement of atoms

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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.

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CH3CH2CH2CH2CH3 pentane

CH3

CH3CHCH2CH3 2-methylbutane

CH3

CH3CCH3 2,2-dimethylpropane

CH3

Write 3 isomers of C5H12 and name each.

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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

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1. Monosubstituteda. group benzene

chlorobenzeneethylbenzene

b. special names:

phenol

2. Benzene as a group- phenyl

Cl CH2CH3

OH

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A carbon compound that contain -OH (hydroxyl) group

CH4 methane

CH3OH methanol

CH3CH3 ethane

CH3CH2OH ethanol

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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

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• 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.

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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

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Contain an -O- between two carbon groups

CH3-O-CH3 dimethyl ether

CH3-O-CH2CH3 ethyl methyl ether

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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

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Functional Groups

CH3CH2CH2CO

H

aldehyde

CH3CH2CCH2CH3

O

ketone

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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

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O O

CH3 -C-CH3 CH3-C-CH2-CH3

propanone 2-butanone

Cyclohexanone

O

Naming KetonesNaming Ketones

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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

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Functional Groups

carboxylic acid

ester

CH3CHCH2CO

OH

CH3

CH3CH2CO

OCH2CH3

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Functional groups

CCH

C

OCH

OH

O

C

C

O

OHO

alcohol alkene

ester

carboxylic acid

ketone

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carboxylic acid

etherester

amine

aldehyde

CHCH2

CO OH

OCH

CH2C

N

NH2

C

O

OCH2

CO

H

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