Organic Chemistry 1. The Chemistry of carbon compounds. 2.

Organic Chemistry

The Chemistry of carbon compounds.

Organic Chemistry

We will look at: (1) Naming of simple compounds.

Organic Chemistry

We will look at: (1) Naming of simple compounds. (2) Some simple reactions.

Organic Chemistry

We will look at: (1) Naming of simple compounds. (2) Some simple reactions. (3) Some simple properties.

Organic Chemistry

We will look at: (1) Naming of simple compounds. (2) Some simple reactions. (3) Some simple properties. (4) Some applications will be discussed.

Naming simple organic compounds

Organic compounds are organized in different families, and each family has a root name.

Naming simple organic compounds

Organic compounds are organized in different families, and each family has a root name. Compounds derived from the starting members in the family have their name based on the parent compound from which they are derived.

The key compounds for naming are the hydrocarbons.

The key compounds for naming are the hydrocarbons. There are three basic classifications and some important secondary classifications.

(1) Alkanes

(1) Alkanes (2) Alkenes

(1) Alkanes (2) Alkenes (3) Alkynes

Prefix systemused to name inorganic compounds. This is also used for organic compounds to name the number of substituents. The base names for the alkanes with five or more C atoms are derived directly from these names.

number prefix

1 mon*2 di3 tri4 tetra5 penta6 hexa7 hepta8 octa9 nona10 deca

*Often not employed.

Prefix systemused to name the number of carbon atoms in the longest chain of organic compounds. Note that the ones in blue do not follow from the first four prefixes in the previous table. These entries are sometimes termed the roots for the number of C atoms.

number prefix

1 meth2 eth3 prop4 but5 pent6 hex7 hept8 oct9 non10 dec

Names for organic compounds break up into two groups:

Non-systematic (trivial)

Non-systematic (trivial) Systematic (This will be our focus, though

some of the common names will be mentioned.)

Non-systematic (trivial) Systematic (This will be our focus, though

some of the common names will be mentioned.)

Example: H2O

The non-systematic name is water. The systematic name is dihydrogen oxide.

Number of bonds For the following atoms the typical number of

bonds from each atom is as follows:

Atom Number of bonds H 1 C 4

Atom Number of bonds H 1 C 4 O 2 N 3

Atom Number of bonds H 1 C 4 O 2 N 3 (Note: there are exceptions)

The Alkanes

As far as naming is concerned, the alkanes are the top priority family.

The Alkanes

As far as naming is concerned, the alkanes are the top priority family. Many other names are based on the names used for this group of compounds.

The Alkanes

As far as naming is concerned, the alkanes are the top priority family. Many other names are based on the names used for this group of compounds.

The alkanes have the general formula CnH2n+2

where n = 1, 2, 3, ….

Formula NameCH4 methane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH2CH2CH2CH3 pentane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH2CH2CH2CH2CH3 hexane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH2CH2CH2CH2CH2CH3 heptane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH2CH2CH2CH2CH2CH2CH3 octane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH2CH2CH3 butane

CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane

CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 decane

CH3CH3 ethane

CH3CH2CH3 propane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3(CH2)3CH3 pentane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3(CH2)4CH3 hexane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3(CH2)4CH3 hexane

CH3(CH2)5CH3 heptane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3(CH2)4CH3 hexane

CH3(CH2)6CH3 octane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3(CH2)4CH3 hexane

CH3(CH2)6CH3 octane

CH3(CH2)7CH3 nonane

CH3CH3 ethane

CH3CH2CH3 propane

CH3(CH2)2CH3 butane

CH3(CH2)4CH3 hexane

CH3(CH2)6CH3 octane

CH3(CH2)7CH3 nonane

CH3(CH2)8CH3 decane

Alkyl groups

Alkyl groupsFormula Name

Alkyl groupsFormula NameCH3 methyl

CH3CH2 ethyl

CH3CH2CH2 n-propyl

CH3CH2 ethyl

CH3CH2CH2 n-propyl

CH3(CH2)2CH2 n-butyl

CH3CH2 ethyl

CH3CH2CH2 n-propyl

CH3(CH2)3CH2 n-pentyl

CH3CH2 ethyl

CH3CH2CH2 n-propyl

CH3(CH2)3CH2 n-pentyl

Ending change: ane yl (or add yl to the root names)

In the previous list “n” stands for normal. In this case the bond is from the first carbon of the longest chain.

In the previous list “n” stands for normal. In this case the bond is from the first carbon of the longest chain. Three other prefixes that occur commonly are:

sec- short for secondary

sec- short for secondary tert- short for tertiary

sec- short for secondary tert- short for tertiary iso (no hyphen is used)

sec- short for secondary tert- short for tertiary iso (no hyphen is used) Examples:

HHHHHH CCCC

Hsec-butyl

HHHHHH CCCC

CCC HH

sec-butyl

tert-butyl

HHHHHH CCCC

CCC HH HH

Hsec-butyl

tert-butyl isobutyl

The term isoalkane is used to denote a branched chain alkane with a methyl group attached to the penultimate carbon atom of the main chain.

As the number of carbon atoms increase, the prefixes become less useful, because an increasingly large number of prefixes would be needed. In this case, the standard numbering scheme (described about nine slides later) is used.

Structures of some alkanes

HHH C CC

HHHHHH CCCC

These are straight chain examples.

HHHHHH CCCC

These are straight chain examples. Note that the alkanes have only single bonds.

HHHHHH CCCC

Branched alkanes

HHHHHH CCCC

Branched alkanes

4 3 2 1

HHHHHH CCCC

Branched alkanes

4 3 2 1 2-methylbutane

(the 2 is a bit redundant)

HHHHHH CCCC

Branched alkanes

4 3 2 1 2-methylbutane

(the 2 is a bit redundant)

Number the longest chain so as to give the lowest number to the substituent (in this case a methyl group) off the main chain.

HHHHHH CCCC

HHHH HH CCCC H

3CH 3CH

5 4 3 2 1

HHHH HH CCCC H

3CH 3CH

5 4 3 2 1 2,3-dimethylpentane

HHHH HH CCCC H

3CH 3CH

HHHHH HH CCCC H

3CH 2CH

C C CH

Note: there is a methyl and an ethyl group off the main chain.

HHHHH HH CCCC H

3CH 2CH

C C CH

1 2 3 4 5 6 7 8

HHHHH HH CCCC H

3CH 2CH

C C CH

8 7 6 5 4 3 2 1 5 and 6 bigger than 3 and 4 – so this is wrong numbering

HHHHH HH CCCC H

3CH 2CH

C C CH

1 2 3 4 5 6 7 8

HHHHH HH CCCC H

3CH 2CH

C C CH

3-methyl-4-ethyloctane (complexity order)

1 2 3 4 5 6 7 8

HHHHH HH CCCC H

3CH 2CH

C C CH

3-methyl-4-ethyloctane (complexity order) 4-ethyl-3-methyloctane (alphabetical order)

1 2 3 4 5 6 7 8

HHHHH HH CCCC H

3CH 2CH

C C CH

Summary of the simple rules to name an alkane. Prefix + root + suffix

Ways of depicting an alkane (p. 578)

The impact of free rotation about carbon – carbon single bonds.

Exercise: Draw the structures of (1) 2,2,3-trimethylbutane (2) 4-ethyl-2-methylnonane (2-methyl-4-ethylnonane) (3) 2,4-dimethyloctane

Physical properties of the alkanes

The series of straight-chain alkanes shows a very smooth gradation of physical properties. As the series is ascended, each additional CH2 group contributes a fairly constant increment to the boiling point and to the density – and to a lesser extent to the melting point.

This makes it possible to estimate the properties of an unknown member of the series from those of its neighbors.

Alkenes

Alkenes These are hydrocarbons with at least one or

more double bonds.

The parent alkanes are used to name the alkene family of compounds.

more double bonds.

The parent alkanes are used to name the alkene family of compounds.

The name ending change is: ane ene

alkane alkene structure ethane ethene

propane propene

alkane alkene structure butane butene

alkane alkene structure butane butene In this case there are three possible compounds.

alkane alkene structure butane butene In this case there are three possible compounds. 1-butene

3CH2CH

alkane alkene structure butane butene In this case there are three possible compounds. 1-butene The number 1 indicates on which carbon the double bond starts.

3CH2CH

alkane alkene structure butane butene In this case there are three possible compounds. 1-butene The number 1 indicates on which carbon the double bond starts. 2- butene

3CH3CHCC

alkane alkene structure butane butene In this case there are three possible compounds. 1-butene The number 1 indicates on which carbon the double bond starts. 2- butene

3CH3CH

alkane alkene structure butane butene In this case there are three possible compounds. 1-butene The number 1 indicates on which carbon the double bond starts. 2- butene cis-2-butene

trans-2-butene

3CH3CH

Z and E isomers

Some cases arise in which it is very difficult to name a compound unambiguously, e.g.

Z and E isomers

Is this a cis or trans compound?

Z and E isomers

A way to sort out this problem is to use the symbols

Z and E isomers

A way to sort out this problem is to use the symbols Z (zusammen = together)

Z and E isomers

A way to sort out this problem is to use the symbols Z (zusammen = together) E(entgegen = opposite)

Rules1. Compare the two groups on one carbon atom of

the carbon-carbon double bond.

the carbon-carbon double bond.2. Assign the two groups priorities using the Cahn-

Ingold-Prelog rules for R and S configurations.

Ingold-Prelog rules for R and S configurations.3. Repeat steps 1 and 2 for the second carbon of the

carbon-carbon double bond.

Ingold-Prelog rules for R and S configurations.3. Repeat steps 1 and 2 for the second carbon of the

carbon-carbon double bond.4. If the two groups of highest priority are on the

same side of the double bond, we have the Z isomer. If the two groups are on opposite sides we have the E isomer.

Arrange the atoms in decreasing order of atomic number, e.g. I, Br, Cl, S, P, F, O, N, C, H

Z-2-butene

3CH3CHCC

Z-2-butene

E-2-butene

3CH3CHCC

Z-2-butene

E-2-butene

E-2-bromo-1-chloro-1-iodopropene

3CH3CHCC

Z-2-butene

E-2-butene

E-2-bromo-1-chloro-1-iodopropene The group of highest priority on each C atom is

circled.

3CH3CHCC

Z-2-butene

E-2-butene

E-2-bromo-1-chloro-1-iodopropene The group of highest priority on each C atom is

circled.

3CH3CHCC

alkene condensed formula ethene CH2CH2

propene CH2CHCH3

1-butene CH2CHCH2CH3

propene CH2CHCH3

2-butene CH3CHCHCH3

propene CH2CHCH3

2-butene CH3CHCHCH3

Note: it would not be clear from the formula for 2-butene whether this is the cis or trans compound.

propene CH2CHCH3

2-butene CH3CHCHCH3

Note: it would not be clear from the formula for 2-butene whether this is the cis or trans compound. This is a reason why structures are very useful!

It is possible to have more than one double bond present. For example:

1,3-butadiene

CCCC H

Alkynes

Alkynes The alkynes have one or more triple bonds.

Alkynes The alkynes have one or more triple bonds. The ending change is: ane yne

Alkynes The alkynes have one or more triple bonds. The ending change is: ane yne The alkenes and the alkynes are referred to as

unsaturated hydrocarbons.

Alkynes The alkynes have one or more triple bonds. The ending change is: ane yne The alkenes and the alkynes are referred to as

unsaturated hydrocarbons.

Unsaturated hydrocarbon: A hydrocarbon having one or more double or triple bonds.

alkane alkyne structure ethane ethyne

propane propyne

H 3CHCC

propane propyne

butane 1-butyne

H 3CHCC

H CC 2CH 3CH

propane propyne

butane 1-butyne 2-butyne

H 3CHCC

H CC 2CH 3CHCC3CH 3CH

alkyne condensed formula ethyne C2H2

propyne CHCCH3

1-butyne CHCCH2CH3

propyne CHCCH3

1-butyne CHCCH2CH3

2-butyne CH3CCCH3

propyne CHCCH3

(Writing C3H4 would not be useful.)

1-butyne CHCCH2CH3

2-butyne CH3CCCH3

propyne CHCCH3

(Writing C3H4 would not be useful. Why?)

1-butyne CHCCH2CH3

2-butyne CH3CCCH3

Explanation of why C3H4 would not be useful.

Clearly, this could be propyne.

CCH 3CH

But it could also be

1,2-propadiene

1,2-propadiene (The numbering would be a bit redundant in this

example.)

Cycloalkanes

The cyclo compounds have a ring of carbon atoms present in the compound.

alkane cycloalkane structure propane cyclopropane

butane cyclobutane

HHH HH

Conformational possibilities for cyclohexane

Some substituents

Substituent Name F fluoro

Some substituents

Substituent Name F fluoro Cl chloro

Some substituents

Substituent Name F fluoro Cl chloro Br bromo

Some substituents

Substituent Name F fluoro Cl chloro Br bromo I iodo

Some substituents

Substituent Name F fluoro Cl chloro Br bromo I iodo

Note: the ending change ide o as in chloride to chloro

Name the following

Name the following1.

HBrHHHH CCCC

Name the following1. fluoromethane

HBrHHHH CCCC

2. 1,1-difluoroethane

HBrHHHH CCCC

3. 1-chloro-1,2-difluoropropane

HBrHHHH CCCC

3. 1-chloro-1,2-difluoropropane

4. 1,2,3-tribromobutane

HBrHHHH CCCC

3. 1-chloro-1,2-difluoropropane*

4. 1,2,3-tribromobutane* *(there is more than one form of this compound)

HBrHHHH CCCC

Some simple reactions of alkanes, alkenes, and alkynes

Combustion: CH4 + 2 O2 CO2 + 2 H2O

When the products are CO2 and H2O it is termed a complete combustion.

With insufficient O2, CO will be formed. E. g.

2 CH4 + 3 O2 2 CO + 4 H2O

With insufficient O2, CO will be formed. E. g.

2 CH4 + 3 O2 2 CO + 4 H2O

This is called an incomplete combustion.

Organic Chemistry 1. The Chemistry of carbon compounds. 2.

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