Organic chemistry
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Organic Chemistry. 1 2 3 4 bonds. Topic 10.1.1 – 10.1.8. H O N C. What is organic chemistry?. study of carbon, the compounds it makes, and the reactions it undergoes over 16 million carbon-containing compounds are known

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Organic Chemistry

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Organic chemistry

Organic Chemistry

1234 bonds

Topic 10.1.1 – 10.1.8

HONC


What is organic chemistry

What is organic chemistry?

  • study of carbon, the compounds it makes, and the reactions it undergoes

  • over 16 million carbon-containing compounds are known

  • because the C-C single bond (348 kJ mol-1) and the C-H bond (412 kJ mol-1) are strong, carbon compounds are stable

  • carbon can form chains and rings


Homologous series compounds 10 1 1

Homologous series/compounds (10.1.1)

  • related compounds that have the same functional group (groups of atoms found within molecules that are involved in the chemical reactions characteristic of those molecules)


Organic chemistry

  • differ from each other by a CH2 unit

  • can be represented by a general formula

    • examples:

      • CnH2n+2 (alkanes) or CnH2n (alkenes) or…


Organic chemistry

  • have similar chemical properties

  • have physical properties that vary in a regular manner as the number of carbon atoms present increases

    • Example: the alkanes


Trends in boiling points of members of a homologous series 10 1 2

Trends in boiling points of members of a homologous series (10.1.2)

  • melting point and boiling point increase with more carbon atoms

  • Why?

    • intermolecular forces increase

    • adding a CH2 adds more electrons

      • this increases the Van der Waal’s forces


Organic chemistry

Empirical, molecular & structural formulas (10.1.3)


Organic chemistry

  • empirical formula

    • simplest ratio of atoms in a molecule

  • molecular formula

    • actual numbers of atoms in a molecule


Organic chemistry

structural formula

  • unambiguously shows how the atoms are bonded together

  • can use condensedstructural formulas

    • bonds are omitted, repeated groups put together, side chains put in brackets

      • CH3CH2CH2CH2CH2CH3

        • or even CH3(CH2)4CH3

      • CH3CH(CH3)CH3(this is not the molecule above)


Organic chemistry

condensed


Organic chemistry

skeletal formula

  • not accepted in the IB for answers but often used

  • every “corner” represents a carbon

  • hydrogens are implied


Isomers 10 1 4

Isomers (10.1.4)

  • (structural) isomers: compounds with the same molecular formula but different structure (arrangement of atoms)


Organic chemistry

  • different isomers are completely different compounds

  • have different physical properties such as melting point and boiling point


Organic chemistry

Structural Formulas for C4H10O Isomers


Structural formulas for the isomers of non cyclic alkanes up to c 6 10 1 5

Structural formulas for the isomers of non-cyclic alkanesup to C6(10.1.5)

Alkanes

  • hydrocarbon chains where all the bonds between carbons are SINGLE bonds

  • CnH2n+2

  • draw out and write the structural formulas for all isomers that can be formed by:

    • CH4

    • C2H6

    • C3H8

    • C4H10

    • C5H12

    • C6H14

Richard Thornley 10.1.5

2:54


Naming the isomers iupac of non cyclic alkanes up to c 6 10 1 6

  • Monkeys

  • Eat

  • Peeled

  • Bananas

Naming the isomers (IUPAC) of non-cyclic alkanes up to C6(10.1.6)

  • Richard Thornley 3:35

  • Determine the longest carbon chain

    • Use the prefix to denote the number carbons


Organic chemistry

  • use the suffix “-ane” to indicate that the substance is an alkane

  • number the carbons in the chain consecutively, starting at the end closest to a substituent (groups attached to the main chain/most busy end)


Organic chemistry

  • name and number the location of each substituent

    • the name of the substituent will be written before the main chain and will end with “–yl” (or just memorize the below)

      • CH3 is methyl

      • C2H5 is ethyl

      • C3H7 is propyl

        And with 2 or more side chains:

  • use prefixes di-, tri-, tetra-, to indicate when there are multiple side chains of the same type

  • use commas to separate numbers and hyphens to separate numbers or letters.

  • name the side chains in alphabetical order


Organic chemistry

  • How about C5H12? The isomers are:

    Pentane 2-methyl-butane dimethyl-propane


Structural formulas for the isomers of the straight chain alk enes up to c 6 10 1 7

Alkenes

Structural formulas for the isomers of the straight chain alkenesup to C6(10.1.7)

  • alkenes have a double bond between two or more of the carbons

  • CnH2n

  • draw out and write the structural formulas for all isomers that can be formed by each

    • C2H4

    • C3H6

    • C4H8

    • C5H10

    • C6H12

Richard Thornley 10.1.7 (1:37)


Nomenclature practice

Nomenclature Practice

Name this compound

Step #1: For a branched hydrocarbon, the longest continuous chain of carbon atoms gives the root name for the hydrocarbon

1

9 carbons = nonane

2

4

3

5

6

7

8

9


Nomenclature practice1

Nomenclature Practice

Name this compound

9 carbons = nonane

1

2

4

3

5

6

CH3 = methyl

7

chlorine = chloro

8

9

Step #2: When alkane groups appear as substituents, they are named by dropping the -ane and adding -yl.


Nomenclature practice2

Nomenclature Practice

Name this compound

Step #3: The positions of substituent groups are specified by numbering the longest chain of carbon atoms sequentially, starting at the end closest to the branching.

9 carbons = nonane

1

2

4

3

5

6

CH3 = methyl

7

chlorine = chloro

8

9

1

9

NOT

9

1


Nomenclature practice3

Nomenclature Practice

Name this compound

Step #4: The location and name of each substituent are followed by the root alkane name. The substituents are listed in alphabetical order (irrespective of any prefix), and the prefixes di-, tri-, etc. are used to indicate multiple identical substituents.

9 carbons = nonane

1

2

4

3

5

6

CH3 = methyl

7

chlorine = chloro

8

9

2-chloro-3,6-dimethylnonane


Organic chemistry

Naming the isomers (IUPAC) of straight chain alkenes up to C6(10.1.8)

  • suffix changes to “-ene”

  • when there are 4 or more carbon atoms in a chain, the location of the double bond is indicated by a number

  • begin counting the carbons closest to the end with the C=C bond

    • numbering the location of the double bond(s) takes precedence over the location of any substituents

1-butene 2-butene

but-1-ene but-2-ene


Naming practice

Naming Practice!!!

choose the correct ending

ene


Organic chemistry

determine the longest carbon chain

ene


Organic chemistry

assign numbers to each carbon

ene


Organic chemistry

assign numbers to each carbon

ene


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attach prefix (according to # of carbons)

ene

1-hexene


Organic chemistry

ethyl

methyl

methyl

determine name for side chains

1-hexene

1-hexene


Organic chemistry

ethyl

methyl

methyl

attach name of branches alphabetically

2-ethyl-4-methyl-4-methyl-1-hexene

1-hexene


Organic chemistry

ethyl

methyl

methyl

group similar branches

2-ethyl-4-methyl-4-methyl-1-hexene

1-hexene


Organic chemistry

ethyl

methyl

methyl

group similar branches

2-ethyl-4,4-dimethyl-1-hexene

or 2-ethyl-4,4-dimethy hex-1-ene


Organic chemistry

propene

2,4-dimethyl-2-pentene

2,4-dimethyl pent-2-tene

2-butene


Organic chemistry

a) 3,3-dimethyl-1-pentene

b) same

C

H

3

C

H

C

C

C

H

C

H

C

H

3

3

C

H

3

c) 4,5 dimethyl-2-hexene


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