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Organic chemistry. Organic Compounds. Organic Compounds - any covalently bonded compound containing carbon except carbonates CO 3 - , carbon monoxide CO, carbon dioxide CO 2 and acetates C 2 H 3 O 2 -. A. Organic Nomenclature. General Characteristics of Organic Molecules.

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organic compounds
Organic Compounds
  • Organic Compounds - any covalently bonded compound containing carbon
  • except carbonates CO3-, carbon monoxide CO, carbon dioxide CO2 andacetates C2H3O2-
general characteristics of organic molecules
General Characteristics of Organic Molecules
      • Carbon always forms 4 covalent bonds
  • due to its hybridization of its s and p
  • orbitals
stabilities of organic molecules
Stabilities of Organic Molecules
  • Carbon forms very strong bonds between H, O, N, and halogens.
  • Carbon also forms strong bonds with itself.
    • Therefore, C can form stable long chain or ring
  • structures.
  • Bond strength increases from single to double to
    • triple bond.
  • Bond length decreases in the same direction.
hydrocarbons
Hydrocarbons
  • Hydrocarbons- Organic compounds that contain only carbon & hydrogen
  • Alkanes- contain only single covalent bonds
  • Alkenes- contain one or more carbon - carbon
  • double bond
  • Alkynes- contain one or more carbon-carbon triple
  • bond
saturated unsaturated hydrocarbons
Saturated & Unsaturated Hydrocarbons
  • Saturated hydrocarbons – contain only single carbon-carbon bonds (alkanes)
  • Unsaturated hydrocarbons – contain double
  • carbon-carbon bonds (alkenes)
  • or triple carbon-carbon (alkynes) bonds
formulas
Formulas
  • Alkanes = CnH2n+2
  • Alkenes = CnH2n
  • Alkynes = CnH2n-2
nomenclature
Nomenclature
  • Must memorize prefixes
  • To name, look at the formula for the hydrocarbon
  • Determine if it is an alkane, alkene, or alkyne
  • Use the prefix for the number of carbons
  • Add ending (ane, ene, yne)
structural formulas
Structural Formulas
  • “Lazy” way to write the Hydrogens
  • Instead of drawing the bonds, just state how many hydrogens are attached
  • NOTE: The bonds are between CARBONS in a parent chain, and not hydrogens!

Structural Formula

Lewis Structure

slide12
B. the first ten alkanes
  • CH4 - methane
  • C2H6 - ethane
  • C3H8 - propane
  • C4Hl0 - butane
  • C5H12- pentane
slide13
C6H14 - hexane
      • C7H16 - heptane
      • C8H18 - octane
  • C9H20 - nonane

C10H22 - decane

slide14
C. the general formula is CnH 2n +2

1. where n stands for the number of carbons

D. Branched chain saturated hydrocarbons

1. must name the longest straight chain

2. number the straight chain so the branches

have the lowest number

slide15
3 list the branches in alphabetical order

e.g. 3-ethyl 2 methyl hexane

slide16
e.g. 3-ethyl 2 methyl hexane

Draw back bone for compound = in this case it is hexane

C

C-C-C-C-C-C

1

2

3

4

5

6

C

C

Number the carbons

Attach branch group

Make sure all C have 4 bonds

designate the location
Designate the Location

Designate the location (number of the carbon on

the parent chain) for each attached group

2-methyl

1 2 3 4 5

2 - methyl pentane

some simple alkanes
Some Simple Alkanes

2-methylpentane

  • 2,2-dimethylbutane

3-ethylhexane

  • 2,3-dimethylbutane
slide20
II. Types of formulas

Structural formulas - shows the

structure of a molecule

B. Condensed structural formulas

slide21
III. cyclic hydrocarbon
      • A. named with the prefix cyclo
  • e.g. cyclohexane
drawing and naming cycloalkanes
Drawing and Naming Cycloalkanes

Cycloalkanes are represented by polygons. A triangle represents cyclopropane, a square represents cyclobutane, a pentagon represents cyclopentane, and so on.

alkenes and alkynes
Alkenes and Alkynes
  • Unsaturated
    • contain carbon-carbon double and triple bond to which more hydrogen atoms can be added.
  • Alkenes: carbon-carbon double bonds
  • Alkynes: carbon-carbon triple bonds.
slide24
IV. alkenes - doubled bonded hydrocarbons considered

to be unsaturated

a. the double bond is located between two C

i. ethene

      • H- C = C - H
      • I I
  • H H

b. change the ane ending to ene

slide25
c. in very large molecules you must give a number

where the double bond begins

e.g. 2- butene

d. If there are more than one double bond the ene

is preceded by number of double bonds

1.3 pentadiene

V. Alkynes - triple bonded hydrocarbons - also unsaturated

A. the triple bond is located between the two C

1. ethyne

H-C=C-H

slide26
B. change the ane ending to yne

C. must also indicate where the triple bond starts

e.g. 2-pentyne

naming alkenes and alkynes
Naming Alkenes and Alkynes

When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the double or triple bond.

1 2 3 4

CH2=CHCH2CH3 1-butene

CH3CH=CHCH3 2-butene CH3CCCH3 2-butyne

endings
Endings
  • Alkanes (all C-C single bonded parent chain) end in –ane
    • MethaneCH4
    • EthaneC2H6
    • PropaneC3H8
  • Attached carbon groups (substituents) end in –yl
    • Methyl CH3 -
    • EthylCH3CH2-
    • Propyl CH3CH2CH2 –  

3-ethylpentane

slide29
VII alkyl halides

The attachment of a Halogen to a carbon group

(F, Cl, Br, I)

Chloro methane

dicloro, difluoro methane

2 – bromo butane

slide30
VII. alcohols - contain OH groups

A. ethanol

B. change the e to ol

C. methane to methanol

VIIIKetones - contains double bonded oxygen

located anywhere but the end

A. change to e to one

B. propane to propanone

slide31
IXaldehydes - contains double bonded oxygen only

at the end

A. change e to al

B. ethane to ethanal

X carboxylic Acid - contain a double bonded oxygen

and a hydroxylgroup

A. change to e to oic acid

B. ethane to ethanoic acid

X I ethers

A. two alkyl groups attached to an oxygen

B. dimethyl ether

aromatic compounds and benzene
Aromatic Compounds and Benzene

Aromatic compounds contain benzene.

Benzene, C6H6 , is represented as a six carbon ring with 3 double bonds.

Two possible resonance structures can be drawn to show benzene in this form.

slide33
When Benzene rings are attached to groups that have higher priorities – it is

known as a phenyl group (C6H5-)

slide37
CO2H

O

I

N

C

R

E

A

S

I

N

G

-CH

O

C

-OH

C=C

R-,C6H5-,Cl-, Br-, NO2

isomers
Isomers
  • Straight chain alkanes: An alkane that has all its carbons connected in a row.

Branched chain alkanes: An alkane that has a

branching connection of carbons.

  • Isomers:Compounds with same molecular formula
  • but different structures.
slide39
F. structural isomers

1. same molecular formula put differ in

structural formula

2. 4 carbon alkane has two possible isomers

3. C5H12 has 3 isomers

4. C6H14 has 5 isomers

5. C10H22has 75

slide40
Carbons in butane (C4H10) can be arranged in two ways; four carbons in a row (linear alkane) or a branching (branched alkane). These two structures are two isomers for butane.
slide41
Different isomers are completely different compounds. They have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.
learning check
Learning Check
  • Draw all possible structural isomers of C5H12

pentane

2-methlyl butane

2,2 – dimethyl propane

example
Example
  • Name C3H8
  • This falls under the equation CnH2n+2
  • Therefore it is an alkane
  • Since n=3 we will use the prefix prop
  • Since it is an alkane we will use the ending ane
  • propane
example1
Example
  • What is the formula for octene?
  • Since the ending is -ene we know that it is an alkene (CnH2n)
  • Since the prefix is oct we know there are 8 carbons
  • C8H16
example2
Example
  • Name C5H12
  • 5 carbons = pent
  • CnH2n+2 = alkane (ane)
  • pentane
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