Alkanes and their Stereochemistry

Functional Groups

●​ Structural features that make it possible to

classify compounds into different families
●​ Group of atoms within a molecule that has a
characteristic chemical behavior
●​ Every functional group behaves almost the
same way in every molecu
●​ Functional groups with carbon singly
bonded to an electronegative atom
●​ Alkyl halides (halogen bonded to C),
alcohols (-OH), ethers (C-O-C), alkyl
phosphates (-PO,*), amines (-NH,), thiols
(-SH), sulfides (C-S-C), disulfides
(C-S-S-C)

●​ Functional groups with carbon-oxygen

●​ Carbon-Carbon Multiple Bonds double bond (carbonyl group)
●​ Alkenes (double bonds), alkynes (triple ●​ Aldehydes (-СОН), ketones (-CO-C),
bonds), and arenes (alternating double and carboxylic acids (-CO-ОН), esters
single bonds in a six-membered ring) (-CO-O-), thioesters (-CO-S-), amide
(-CO-NH2), acid chloride (-CO-Cl)

●​ Functional groups with carbon singly

bonded to an electronegative atom
●​ Alkyl halides (halogen bonded to C),
alcohols (-OH), ethers (C-O-C), alkyl
phosphates (-PO,*), amines (-NH,), thiols
(-SH), sulfides (C-S-C), disulfides
(C-S-S-C)
Alkanes and Isomers

Alkanes

●​ All alkanes are simple chain of carbon

atoms covalently bonded together.
●​ They are also known as saturated
hydrocarbons
●​ Hydro for hydrogen and carbons for the
atom
●​ General formula of alkanes: CnH2n+2
●​ Occasionally known as aliphatic compounds

Alkanes

●​ Alkanes can be arranged in different ways.

The more carbons, the more ways they can
be arranged
●​ Linear chains: straight-chain (normal)
alkanes
●​ Non-linear: branched-chain alkanes
●​ Compounds that have the same number of
atoms but are arranged differently from
each other are called constitutional
isomers.
Alkyl Groups

●​ If you remove a hydrogen from an alkane,

what is left is called an alkyl group.
●​ Alkyl groups are unstable compounds; they
are parts of larger compounds.
●​ Named by replacing the -ane of the alkane
by -yl.

●​ Suffix iso- is given to 2-methyl groups; if a

methyl group is found on the second carbon
of carbon chain, iso- is used.
●​ Sec-(secondary) and tert- (tertiary) in C4
alkyl groups refer to the number of carbon
atoms attached to the branching carbon
atom.

Four possibilities:

●​ Hydrogens are also categorized as primary,

secondary, and tertiary atoms
 ●​ If two or more substituents are present,
arrange them alphabetically regardless of
their location on the chain
●​ If two or more substituents are identical, use
the suffixes di-, tri-, tetra-, and so forth.

Step 5: Name a complex substituent as though

it is a compound

●​ Only for complex compounds, especially if

Naming Alkanes the substituent has a sub-branching
●​ Substituent is treated as a whole and is
●​ According to the International Union of Pure alphabetized according to its first letter. A
and Applied Chemistry (IUPAC), a chemical parenthesis is used to set it off from the rest
name has four parts of the name.

For historical reasons, some simpler

branched-chain alkyl groups also have
nonsystematic, common names.

When used, iso- is included in alphabetizing, but

●​ Locant are numbers that refer to the sec-and tert- are not.
position at which the substituent is
connected to the carbon chain; prefix
determine what substituents are present;
parent refers to the number of carbon(s);
suffix determines the primary functional
group.

Step 1: Find the parent hydrocarbon. Usually,

the longest carbon chain

●​ You may have to turn corners.

●​ If the chain has even number of carbons,
start counting at the end with the most
number of branches.

Step 2: Number the atoms of the longest chain

●​ Beginning at the end nearer the first branch,

number the carbon atoms.

Step 3: Identify and number the substituents

●​ Assign the a number on the substituent to

determine its location in the chain.
●​ If there are two substituents on the same
carbon, give both the same number.

Step 4: Write the name as a single word

●​ Use hyphens to separate the different

prefixes
●​ Use commas to separate locants
Properties of Alkanes

●​ Alkanes are sometimes referred to as

paraffins: parum affinis, meaning little
affinity
●​ Alkanes are generally stable, which gives
them little affinity for other substances. They
are chemically inert to most lab reagents.
●​ However, they react with oxygen, halogens
(Family VII), and few other substances
under appropriate conditions.
●​ Alkanes are used as fuel for combustion to
yield CO, and H,0.
●​ Reaction with chlorine gas (Cl,) occurs
when both are irradiated (exposed) with UV
light.
●​ Depending on the concentration of both,
sequential substitution reaction occurs,
leading to a mixture of chlorinated products.
●​ As molecular weight of an alkane increases
(longer chains), their relative boiling point
and melting point also increases.
●​ Increased branching lowers the boiling.
●​ Branched-chain have lower boiling points
because they are more spherical, have
smaller surface area, and have smaller
dispersion forces.