Chapter 8: Hydrocarbons and Haloalkanes

Organic Chemistry

Is the subdivision into separate compounds determined by the elements and the functional groups that are present

Hydrocarbons

• simplest group of organic compounds
• compound only containing Hydrogen and Carbon

aliphatic/acyclic and aromatic/cyclic

Hydrocarbons can be further classified into what two groups?

Aliphatic/Acyclic Hydrocarbons

open-chains of carbon to carbon bonds

Aromatic/Cyclic Hydrocarbons

ring formed chains of carbons

Aliphatic Hydrocarbons

A carbon to carbon interaction where single covalent bonds are formed

Alkanes

• Aliphatic hydrocarbons: A carbon to carbon interaction where single covalent bonds are formed
• Classified as Saturated Hydrocarbons
alk- = Aliphatic hydrocarbon
-ane = Single bonds/saturated
Reactions of alkanes are considered substitution/replacement Paraffin Series/Methane Series)

Saturated Hydrocarbons

Can not hold anymore hydrogens

the Chemical Formula for Alkanes

C_nH2_n+2

International Union of Pure and Applied Chemists (IUPAC)

Who establishes the rules for naming chemicals?

Naming Alkanes

• Name the longest chain of carbons first
• Second, name side chains from largest to smallest
• Name is always written from right to left
• Name is read from left to right
• Identified by the the number of carbons and the prefix.
• Longest chain of carbons would have a suffix of “ane”
• Side chains can be called radicals and have their own prefix then suffix “-yl”

Alkenes

• Aliphatic Hydrocarbons: One carbon to carbon bond is a double covalent bond
• Unsaturated hydrocarbons (double bonds can be broken opening the possibility of more hydrogens to bond)
• alk- aliphatic hydrocarbon
• -ene One double bond present
• Addition reaction: Has the capacity to add a hydrogen with the double bond
• Found in the Olefin Series/Ethane Series

The Chemical Formula for Alkenes

C_nH2_n

Unsaturated hydrocarbons

double bonds can be broken opening the possibility of more hydrogens to bond

Naming Alkenes

• Name the longest chain of carbons with the double bond first (carbons on either side of the double bond should be named with the chain)
• Second, give address to the double bond by using the smallest number
• Third, name the carbon side-chain from largest to smallest
• Name is always written from right to left
• Name is read from left to right
• Prefix: Longest chain of carbons
• Suffixes: -ene: double bond, -yl: carbon side chain/carbon radical

Alkynes

• Aliphatic Hydrocarbons: One carbon to carbon bond is a triple covalent bond.
• Classified as unsaturated hydrocarbons (triple bond can be broken opening the possibility of more hydrogens to bond)
• alk- aliphatic hydrocarbon
• -yne One triple bond present
• Addition reaction: Has the capacity to add a hydrogen with the triple bond
• Found in the Acetylene Series/Ethyne Series

The Chemical Formula for Alkynes

C_nH2_n-2

Naming Alkynes

• Name the longest chain of carbons with the triple bond first (carbons on either side of the double bond should be named with the chain)

• Second, give address to the triple bond by using he smallest number
• Third, name the carbon side-chain from largest to smallest
• Name is always written from right to left
• Name is read from left to right
• Prefix: Longest chain of carbons
• Suffixes: -yne: Triple bond, - yl: Carbon side chain/carbon radical

R

alkyl group

X

Halogen Group

Methyl Trichloride

Continuing to replace a hydrogen with a halogen in methyl chloride will result in…

The Formula for Alkyl Halides/Haloalkanes

Formula R-X

Methyl Trichloride

• Chloroform: Organic solvent

• CHCl₃

Simplest alkyl halide

Methyl Chloride (CH₃CL)

Methyl Tetrachloride (Carbon Tetrachloride)

replacing all the hydrogens with halogens in methyl trichloride would result in…

Methyl Tetrachloride

• Organic solvent
• Non-Flammable = fire extinguishers
• Very toxic fumes
• CCl₄

Carbocyclic Hydrocarbons

Only carbons present in their rings.

Aromatic Hydrocarbons

• Organic compounds that contain only carbon and hydrogen compounds that are arranged in a linkage format to form a ring.
• Called: Cyclic/Closed chain
• Carbocyclic hydrocarbons: Only carbons present in their rings

Cycloalkanes/Cyclanes

• Carbocyclic Hydrocarbons
• Similar to alkanes but in an ring form
• Prefix: Cyclo- ring structure; Prop- 3 carbons in chain
• Suffix: -ane Single bond found between carbons
• Prefix: Cyclo- Ring structure; But- Four carbons in chain
• Suffix: -ane Sing Bond

The Formula for Cycloalkanes/Cyclanes

C_nH2_n

Cyclopropane

Smallest of the cycloalkanes; 3 carbon ring with 2 hydrogens attached to each carbon; single bonds between the carbons; C3H6

Cyclobutane

4 carbons joined by a single bond forming a ring with 2 hydrogens attached to each carbon.

Cycloalkenes

• carbocyclic hydrocarbons
• similar to alkenes – they have a double bond between two carbons and they are found in a ring formation.

Benzene

• Most common cycloalkenes

• Ring of 6 carbons with alternation double bonds and a single hydrogen attached to the carbons

• Formula: C6H6

• Because of it’s unique formation with the double bonds and ring, it defies the rules and does not work under the addition rule but rather is classified as a resonance compound which has a replacement/substitution reaction.