Introduction to Organic Chemistry

Nomenclature
Writing form: Prefix parent locant Suffix Steps: 1. Parent hydrocarbon 2. Number the atoms in main chain 3. Identify and number substituents 4. Write the name as a single word 5. (cycloalkane chair conformation)

Number of C atoms 1 2 3 4 5 6 7 8 9 10

Word root meth Eth Prop But Pent Hex Hept Oct Non Dec

Functional Group Alkane Alkene Alkyne Carboxylic acid Alcohol

Representation C-C single bond C-C double bond C-C triple bond -COOH -OH

Nomenclature

2, 3-dimethybutane

Questions:
1-bromo-1-chlorobutane

2,2-dimethylpentane

Cyclobutane

1,1- dimethylcyclopentane

1,4-dimethylcyclohexane

Lines
Bonds to atoms above the plane of the drawing (coming out, toward the viewer) are shown with a bold wedge ( ), with the narrow end of the wedge starting at the stereogenic center. Bonds to atoms below the plane (going in, away from the viewer) are shown with hash wedges ( ).

Sawhorse representation and Newman projection

Sawhorse representation
Views C-C bond from an oblique angle
Indicated spatial relationships by showing all the C-H bonds

Newman Projection
Views C-C bond directly end-on Carbon atoms are represented by a circle

Available: http://image.wistatutor.com/content/hydrocarbons/newman-projections.gif

Staggered and eclipsed

Sawhorse projection

Newman projection

Stability

Skeletal structures
Propene

Cyclohexane

Benzene

Benzene and phenyl

The benzene ring All aromatic compounds are based on benzene, C6H6, which has a ring of six carbon atoms and has the symbol: Each corner of the hexagon has a carbon atom with a hydrogen attached.

The phenyl group A hydrogen is removed from a benzene ring, C6H6. Like a methyl or an ethyl group, a phenyl group is always attached to something else (not carbon).

Benzene-1,4-dicarboxylic acid

2-hydroxybenzoic acid

2,4,6-trichlorophenol

Functional group
A group of atoms whose bonding is the same from molecule to molecule. Imparts similar chemical and physical properties to the molecules which contain them.

Imine Functional Group

Also called Schiff Base =NH

Imine
Carbonnitrogen double bond Nitrogen attached to a hydrogen atom (H) or an organic group. The carbon has two additional single bonds

Examples of Imines

(E)-N-Benzylidenemethanamin

Rhodopsin, an imine used in vision.

Imines
Related to ketones and aldehydes by replacement of the oxygen with an NR group When R = H, the compound is a primary imine When R is hydrocarbyl, the compound is a secondary imine

R2C=NR'
When R3 is OH, the imine is called an oxime

When R3 is NH2 the imine is called a hydrazone

Aldimines and ketimines

A primary imine in which C is attached to both a hydrocarbyl and H is called a primary aldimine

A secondary imine with such group is called a secondary aldimine

 A primary imine in which C is attached to two hydrocarbyls is called a primary ketimine

A such group is called a secondary ketimine.

Naming Imines
Imines are systematically named by adding the word imine after the name of the corresponding aldehyde or ketone CH3CHNH ethanal imine (from ethanal, CH3CHO) Btw, is this a primary/secondary aldimine/ketamine?

Naming Imines
(CH3)2CNH Propanone imine Ethanal methyl imine CH3CHNCH3

Nitrile
CN

Nitriles
any organic compound that has a CN functional group Inorganic compounds containing the -CN group are not called nitriles, but cyanides

Naming Nitriles
2 ways of naming nitriles

Cyano substituent style

- The root name is based on the longest chain with the -CN as a substituent. - Chain is numbered so as to give the -CN group the lowest possible locant number - E.g. 1-cyanopropane

Nitrile Style
The nitrile suffix is used in a very similar manner to carboxylic acids Faced with same compound, CH3CH2CH2CN Functional group is a -CN, therefore suffix = nitrile Hydrocarbon structure is an alkane therefore Longest chain is C4 Butanenitrile

Naming Nitriles (nitrile style)

Benzonitrile

Cyclopentanecarbonnitrile

Naming Nitriles
Butanedinitrile

2-methyl-1-propanenitrile Bonus! How do you name this?

Nitro Functional Group

RNO2

Nitro Functional Group

O-N=O central nitrogen atom is involved in both a double bond and a single bond Highly explosive, various impurities or improper handling can easily trigger a violent exothermic decomposition (aka an explosion) An example is nitroglycerin

Nitro R-NO2
Aromatic nitro compounds. Trinitrotoluene (TNT) - A pale yellow, solid organic nitrogen compound used chiefly as an explosive, prepared by stepwise nitration of toluene

Reactions: Reduction
Nitro compounds are reduced to amines RNO2 + 3 H2 RNH2 + 2 H2O

Naming Nitro Compounds

Simply name the -NO2 as a nitro substituent

Naming Nitro Compounds

Nitromethane Guess how Nitrobenzene looks like?

Thiol Functional Group

Thiols
Organosulfur compound that contains a carbon-bonded sulfhydryl (-C-SH or R-SH) group Have a foul smell Structurally similar to an alcohol but contains a sulfur atom in place of the oxygen atom normally found in an alcohol. Among the odorous principles in the scent of skunks and of freshly chopped onions

Synthesis
Reaction of related alcohol with hydrogen sulphide CH3OH + H2S CH3SH + H2O

Naming Thiols
Sulfur analogues of alcohols Named the same way too The root name is based on the longest chain with the -SH attached. The chain is numbered so as to give the thiol unit the lowest possible number. The thiol suffix is added after the hydrocarbon suffix : e.g. -ane + -thiol = -anethiol or -ene + thiol = -enethio

Naming Thiols
CH3CH(SH)CH3 Propan-2-thiol or 2-propanethiol

1-Butanethiol

Cyclopentanethiol

Naming Thiols

4-methylpentan-2-thiol

Sulphide Functional Group

Also known as Thioether

Sulphides
S atom bonded to two C atoms via s bonds R-S-R Named the same way as oxygen cousins, ethers Like many other sulfur-containing compounds, volatile thioethers characteristically have foul odors

Naming Sulphides: "Simple" thioethers

"Simple" thioethers If both groups are simple alkyl groups, then the thioether is usually named as alkyl alkyl thioether Alkyl groups are listed in alphabetical order If the two alkyl groups are the same, then it's a dialkyl thioether CH3-S-CH3 Dimethylsulphide CH3CH2SCH3 Ethyl Methyl

Intermediate Thioethers
If one of the groups is more complex then the thioether group is usually treated as an alkylthio- (i.e. R-S-) substituent. The more complex group (i.e. longer chain, more branched, other substituents) defines the root CH3CH2CH2SCH3
1-methylthiopropane

Complex Thioethers
If both groups are complex then the ether can be named using thio E.g. CH3SCH2CH2CH3 Hydrocarbon structure is an alkane Functional group is an thioether, therefore prefix = -thio The longest continuous chain (including the S) is 5 therefore root = pent Numbering from the left as drawn to make the thio group locant 2 2-thiopentane

Examples (Simple)

Butyl ethyl sulphide

Disulphides

Disulphide bond
Covalent bond, usually derived by the coupling of two thiol groups Also known as sulphide bridge

Disulphide Bond
Play an important role in the folding and stability of proteins E.g. two-amino-acid peptide cystine Composed of two cysteine amino acids joined by a disulfide bond

Ever wondered why hair doesnt seem to decompose along with dead bodies?
Over 90% of the dry weight of hair comprises proteins called keratins from the amino acid cysteine Hair has a high disulfide content The robustness conferred in part by disulfide linkages Recovery of virtually intact hair from ancient Egyptian tombs