4.

3 IUPAC naming of alkanes

Meth-1 Hex-6 undec-11

Eth-2 Hept-7 dodec-12

Prop-3 Oct-8

But-4 Non-9

Pent-5 dec-10

Rules

1. Locate longest continuous chain of carbon atoms. This is parent. Add 'ane' to prefix for that number
of carbons

1.a Substituents: count number of carbons in substituent and name by adding 'yl' instead of 'ane'

2. Number parent chain to give smallest number to carbon bearing first encountered substituent.

3. Use numbers obtained from rule 2 to designate location of substituent. Numbers are separated by
hyphens (but not words)

4, 5. Two or more substituents present? List alphabetically, but number to give lowest number to first
encountered. Use number twice, if needed.
6. Use prefixes di, tri, tetra, penta, hexa, etc. to show how many of each type of substituent. (Di, tri,
tetra, etc. not considered for alphabetizing.)

7. If two chains compete for longest, choose chain with the most subsituents.

8. If first encountered substituent would get same number if you number from two directions, number
to give lowest to first point of difference.

4.C If substituents are branched, some common names to memorize

Isopropyl sec-butyl

Isobutyl tert-butyl (t-butyl or t-Bu)

Otherwise: Carbon of attachment is C-1. Find longest chain, number to show location of substituent's
substituents. Put in parentheses.

4.3D Primary, secondary tertiary H's

Classified depending upon how many carbons attached to carbon that the H is attached to
4.3E alkyl halide naming. Treat halogen exactly like other substituent.

F- fluoro Cl- chloro Br- bromo I- iodo

Old system: halogen is parent. Chain is substituent

4.3 F alcohols.

1. Select longest chain that contains carbon that bears the -OH. It is parent. Change ending of alkane
from 'e' to 'ol'.

2. Give the carbon that –OH is on the lowest number. Indicate that carbon's position with number
before parent or before 'ol'. Then proceed like always.
---Common: 'alcohol' is parent. Chain is substituent.

---Diol, triol, tetraol, etc. used to indicate more than one OH.

4.4A Cyclic

1. Add 'cyclo' to parent. (i.e., number of carbons in ring) . Number to give C-1 to lowest substituent
alphabetically. (Unless –OH is present; then it is C-1, and doesn't need to be numbered.

Number in direction to give lowest to first point of difference.

(Ring can be a substituent, too)

4.4B Bicyclo

1. Count total carbons in bicyclo system. That is parent.

Bicycle [ ]'parent' ane

2. In brackets, put the number of carbons in each bridge, in decreasing order.

3. Number starting at bridgehead, then around largest ring, then next largest, etc. Give substituents
lowest possible number (after other rules are followed.)
4.5 Alkenes

Choose parent by selecting longest chain that contains double bond. Change 'ane' in parent to 'ene'.

Number chain to include BOTH C's of double. Show location by using number of first encountered C of
double bond. Make that number as low as possible.

Proceed as always.

Cycloalkene: C's of double bond are C-1 and C-2. Give lowest number possible to first encountered
substituent, and then proceed as always

4.6 alkynes: much like alkenes.