91Ó°ÊÓ

Question: Write the structure for the following compounds.

(a) 3-ethyl-4-methylhexane

(b) 3-ethyl-5-isobutyl-3-methylnonane

(c) 4-tert-butyl-2-methylheptane

(d) 5-isopropyl-3,3,4-trimethyloctane

In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.

(a) Nonane or 3-methylheptane

(b) Octane or 2,3,4-trimethylpentane

(c) 2,3,5-trimethylhexane or nonane

Question: Convert each Newman projection to the equivalent line-angle formula, and assign the IUPAC name.

Question: Draw Newman projections along the C3-C4bond to show the most stable and least stable conformations of 3 ethyl-2,4demethylheptane.

Question: Conformational studies on ethane-1,2-diol (HOCH₂ -CH₂OHhave shown the most stable conformation about the central C-Cbond to be the gauche conformation, which is 9.6 KJ/mol (2.3 kcal/mol)more stable than the anti-conformation. Draw Newman projections of these conformers, and explain this curious result.

Question: The most stable form of 1,2,3,4,5,6-Cyclohexanehexolcontains a six-membered ring in the chair conformation with all the substituents equatorial. Draw this most stable conformation of cyclohexanehexol

Question: This is a Newman projection of a substituted cyclohexane.

(a) Draw the equivalent chair form

(b)Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.

(c) Give the IUPAC name.

Question: All of the following names are incorrect or incomplete. In each case, draw the structure ( or a possible structure) and name it correctly

Draw the structures of the following compounds.

(a) 4-(1,1-dimethylethyl)nonane

(b) 5-(1,2,2-trimethylpropyl)decane

(c) 3,3-diethyl-4-(2,2-dimethylpropyl)nonane

Name the following alkane and haloalkane. When two or more are present list them in alphabetical order.