CHEM 3312: General Organic Chemistry

2^nd Homework Assignment – Due September 26^th

A particular isomer of geraniol is an essential oil that is used as a base in the manufacture of perfumes. Its IUPAC name is (Z)-3,7-dimethyl-2,6-octadiene-1-ol (I will refrain from giving you its common name as its structure is shown in the Merck Index.)

1. Draw the structure of this essential oil.

Reference textbook problems: 6.11, 6.23, 6.24, 6.25, 17.1, 17.2

2. This compound easily reacts to form 4-(propene-2-yl)-1-methyl-1-cyclohexene (common name: dipentene). Draw the structure of dipentene.

Reference textbook problems: 6.5, 6.6

3. Propose a mechanism for the conversion of the essential oil you drew in part 1 to the dipentene structure you drew in part 2 under mildly acidic conditions.

Reference textbook problems: 17.12, 17.32, 17.35, 17.37, 17.38, 17.43

4. Identify a spectroscopic method you could use to follow the reaction above, and describe the spectral features unique to the reactant (the essential oil) and the product (dipentene).

Reference textbook problems: 13.33, 13.36, 13.37, 13.38, 17.16

5. If the essential oil were to be synthesized using a Grignard reaction, draw the structures of a Grignard reagent and a carbonyl compound that could be used as starting materials.

Reference textbook problems: 17.9, 17.10, 17.25, 17.30