4. Organic Compounds: Cycloalkanes and their Stereochemistry

Saturated cyclic hydrocarbons are called ____________

cycloalkanes

cycloalkanes are also called _______ compounds (aliphatic cyclic)

alicyclic

Because cycloalkanes consist of rings of −CH₂−units, they have the general formula (CH₂)_n, or C_nH_2n, and can be represented by _________ in skeletal drawings.

polygons

Naming a _____________:

step 1) find parent

step 2) number the substituents, and write the name

cycloalkane

when finding the parent of a cycloalkane, if the number of carbon atoms in the ring is greater or equal to the number of carbon atoms in the substituent, you prioritize the _____________ as the parent

cycloalkane

when finding the parent of a cycloalkane, if the number of carbon atoms in the ring is less than the number of carbon atoms in the substituent, you prioritize the _____________ as the parent

substituent

Which has more priority when naming: a cycloalkane or an alcohol?

an alcohol

For an alkyl- or halo-substituted cycloalkane, choose a point of attachment as carbon 1 and number the substituents on the ring so that the second substituent has as ___ a number as possible. If ambiguity still exists, number so that the third or fourth substituent has as low a number as possible, until a point of difference is found.

low

When two or more different alkyl groups are present that could potentially take the same numbers, number them by _________ priority, ignoring numerical prefixes such as di- and tri-.

alphabetical

If halogens are present, treat them just like ____ groups.

alkyl

Give IUPAC names for the following cycloalkanes:

1,4-Dimethylcyclohexane

Give IUPAC names for the following cycloalkanes:

1-Methyl-3-propylcyclopentane

Give IUPAC names for the following cycloalkanes:

3-Cyclobutylpentane

Give IUPAC names for the following cycloalkanes:

1-Bromo-4-ethylcyclodecane

Give IUPAC names for the following cycloalkanes:

1-Isopropyl-2-methylcyclohexane

Give IUPAC names for the following cycloalkanes:

4-Bromo-1-tert-butyl-2-methylcycloheptane

Draw structures corresponding to the following IUPAC names:

(a)

1,1-Dimethylcyclooctane

Draw structures corresponding to the following IUPAC names:

(b)

3-Cyclobutylhexane

Draw structures corresponding to the following IUPAC names:

(c)

1,2-Dichlorocyclopentane

Draw structures corresponding to the following IUPAC names:

(d)

1,3-Dibromo-5-methylcyclohexane

Name the following cycloalkane:

3-Ethyl-1,1-dimethylcyclopentane