Organic Chemistry Chapter 2

mostly for naming

alkanes

saturated hydrocarbons containing single bonds between Carbon atoms

-ane

suffix for saturated hydrocarbons (hydrocarbons with only single bonds)

CH₄

methane

CH₃CH₃

ethane

CH₃CH₂CH₃

propane

CH₃CH₂CH₂CH₃

butane

CH₃CH₂CH₂CH₂CH₃

pentane

CH₃CH₂CH₂CH₂CH₂CH₃

hexane

CH₃CH₂CH₂CH₂CH₂CH₂CH₃

heptane

CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₃

octane

CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₃

nonane

CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₃

decane

CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₃

undecane

CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₃

dodecane

Formula for alkanes

C_nH_2n+2

IUPAC parent name is based on what?

Longest carbon chain counted

Common Name is based on….

Total number of carbons

Order of substituents in naming is dependent on

alphabetical order

What’s the common name for this molecule?

4 carbons: butane

CH₃—CH(CH₃)₂ = includes branches

prefix: iso

Final name: isobutane

What’s the IUPAC name

Longest carbon chain: 3 carbons

Substituent: CH₃ attached to second carbon

2-methylpropane

Name this substituent

methyl Me

Name this substituent

ethyl Et

Name this substituent

propyl Pr

Name this substituent BOTH IUPC AND COMMON NAME

1-methylethyl (isopropyl iPr)

Name this substituent

butyl (Bu)

Name this substituent BOTH IUPC AND COMMON NAME

1-methylpropyl (sec-butyl s-Bu)

Name this substituent BOTH IUPC AND COMMON NAME

2-methylpropyl (isobutyl iBu)

Name this substituent BOTH IUPC AND COMMON NAME

1-dimethyletyl (tert-butyl t-Bu)

Name this substituent

Pentyl

Name this substituent BOTH IUPC AND COMMON NAME

3-methylbutyl (isopentyl)

Name this substituent BOTH IUPC AND COMMON NAME

2,2-dimethylpropyl (neopentyl)

Primary carbons

Carbons bonded to one carbon

Secondary carbons

Carbons bonded to two carbons

Tertiary carbons

Carbons bonded to three carbons

Quaternary carbons

Carbons bonded to four carbons

Primary hydrogens

Hydrogens bonded to a primary carbon

Secondary hydrogens

Hydrogens bonded to a secondary carbon

Tertiary carbons

Hydrogens bonded to a tertiary carbon

Cycloalkane formula

C_nH_2n

Cycloalkanes nomenclature rules (three total)

1. Prefix “Cyclo—”

2. One substituent: no number required

3. Two or more substituents: alphabetically ordered with the lower set of numbers

Bicycloalkane formula

C_nH_2n-2

Bicycloalkanes

are cycloalkanes with two fused rings

In the bracket for bicycloalkanes, what is the first number?

Total number of Carbons in the biggest ring that DOESN’T overlap other ring/bridge

In the bracket for bicycloalkanes, what is the second number?

Total number of Carbons in the smaller ring that DOESN’T overlap other ring/bridge

In the bracket for bicycloalkanes, what is the third number?

Total number of Carbons in bridge (overlapping area)

In the bracket for bicycloalkanes, what are the numbers separated by?

.

Zero carbon bridge

When there are no carbons in bridge

Bicycloalkanes nomenclature (three parts)

1. prefix “Bicyclo—”

2. [number.number.number]

3. prefix (based on total number of carbons) —ane