Organic Chemistry 1.1 Alkanes, Alkanes, Cycloalkanes, Alkenes, Alkynes

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alkanes

Back 1

saturated hydrocarbon

alkanes consist only of hydrogen and carbon bonds (all bonds are single)

Extra: methane, ethane, propane, butane, etc

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meth-

Back 2

1C

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eth-

Back 3

2Cs

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prop-

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3Cs

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but-

Back 5

4Cs

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pent-

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5Cs

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hex-

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6Cs

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hept-

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7Cs

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oct-

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8Cs

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non-

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9Cs

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dec-

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10Cs

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n-alkane

Back 12

Normal alkane. Straight chain alkane.

e.g. n-C4H10

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alkane properties

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n-alkane show:

as molecular weight increases for a given number of carbons in an alkane, increase in BPs and MPs

increasing branching lowers the BP

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alkyl

Back 14

a group formed from an alkane by the removal of a hydrogen atom

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n-alkyl

Back 15

indicates that it is the end hydrogen that is removed from an n-alkane

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primary hydrogen

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any H atom belonging in a CH3 in a molecule

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secondary hydrogen

Back 17

any H atom belonging in a CH2 in a molecule

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tertiary hydrogen

Back 18

any H atom belonging in a CH in a molecule

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primary carbon

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in a molecule, a carbon atom bonded to one (only) other carbon atoms

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secondary carbon

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in a molecule, a carbon atom bonded to two (only) other carbon atoms

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tertiary carbon

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in a molecule, a carbon atom bonded to three (only) other carbon atoms

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quaternary carbon

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in a molecule, a carbon atom bonded to four other carbon atoms

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Steps for naming alkanes

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1. Identify the parent chain

a. identify the longest carbon chain

b. if more than one different chains are of equal length (no of Cs), choose the one with greater number of branch points (substituents)

2. Number the carbons of the parent chain

a. number the C atoms so that any branch points have the lowest possible number

b. if there is branching equidistant from both ends of the P chain, number so the second branch point has the lowest number

3. Substituents

a. identify and number the substituents and list them in alphabetical order

b. if there are two substituents on the same carbon, assign them the same number

4. Write out name

a. write out name as a single word:

hyphens (-) separate prefixes

commas (,) separate numbers

b. substituents are listed in alphabetical order

c. if two or more identical substituents are present, use the prefixes:

di - for two

tri - for three

tetra - for four

(ignore the prefixes di-, tri- tetra-, etc for alphabetising purposes)

5. Complex Substituents (substituents with branching)

a. named by applying above rules with some modification

b. number the complex substituent separately from the parent. begin numbering at the point of attachment to the parent chain.

c. complex substituents are set off by parenthesis.

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cycloalkanes

Back 24

saturated cyclic hydrocarbons

e.g. CnH2n

Extra: cyclopropane (3Cs), cyclobutane (4Cs), cyclopentane (5Cs), cyclohexane (6Cs), cycloheptane (7Cs), cyclooctane (8Cs), cyclononane (9Cs), cyclodecane (10Cs).

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naming cycloalkanes

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1. Parent Chain

a. use the cycloalkane as the parent chain if it has the greatest number of carbons than any alkyl substituent

b. if an alkyl chain off the cycloalkane has a great no of Cs, then use the alkyl chain as the parent and the cycloalkane as the cycloalkyl-substituent

2. Numbering the Cycloalkane

a. when numbering the carbons of a cycloalkane, start with a substituted carbon so that the substituted carbons have the lowest numbers (sum)

b. when two or more different substituents are present, number according to alphabetical order

3. Halogen substituents

Halogen substituents are treated exactly like alkyl groups

flouro-, chloro-, bromo-, iodo-

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alkenes

Back 26

unsaturated hydrocarbons

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naming alkenes

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1. Name the parent hydrocarbon by locating the longest C chain that contains a double bond and name it according to the number of carbons with suffix -ene.

2. a. number the carbons of the parent chain so that double bond carbons have the lowest possible numbers.

b. If a double bond is equidistant from each end, number so that the first substituent has the lowest number.

3. write out full name, numbering the substituents according to their position in the chain and list in alphabetical order

4. indicated the double bond by the number of the first alkene carbon

5. if more than one double bond is present, indicate their position by using the number of the first carbon of each double bond and use the suffix -diene (for 2 double bonds), -triene (for 3 double bonds), -tetraene (for 4 double bonds) etc.

6. a. Cycloalkenes are named in a similar way. Number the cycloalkene so the double bond carbons get no 1 and 2 and the first substituent is the lowest possible number.

b. if there is a substituent on one of the double bond carbons, it gets number 1.

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alkynes

Back 28

unsaturated hydrocarbons

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naming alkynes

Back 29

1. number the carbon chain from the end of the carbon nearest the triple bond

2. the alkyne position is indicated by the number of the alkyne carbon in the chain

3. compounds with two triple bonds are called diynes, three as triynes, etc

Compounds with both triple and double bonds are called enynes.

Numbering starts from the end nearest the multiple bond, whether double or triple. If there is a choice in numbering, the double bond receives the low number.