University of Houston

• CHEM 3331

• 1. Give an acceptable IUPAC name for each of the compounds in a-b. Draw the structure of the compound in c. Be sure to indicate the stereochemistry where appropriate. (15 points) a. b. c. Cis-1-(3,4-dimethylpentyl)-3-tert-pentylcyclooctane 9 g O 5 butyl 4 ethyl 4 2,37 trimethylnonane nonane 2 3,7 trimethyl 2 3,415,7 4 ethyl 5 butyl 3 a trans 1 butyl 4 2,33 trimethylbutyl Z cyclohexane 4 cyclohexane Hz CH3 futz dit fecit trans 1 butyl f Z CH 4543,3 trimethylbutyl distri tert see X neo isu cyclo up At Ishak This study source was downloaded by 100000870480224 from CourseHero.com on 09-22-2023 14:51:53 GMT -05:00 https://www.coursehero.com/file/75799841/test-01-fall-14-filledpdf/ Yi-Kai Lin 2. Place the compounds below in order of increasing boiling point. (1=lowest, 3=highest boiling point) (6 pts.) 3. Place the compounds below in order of increasing solubility in hexane. (1=least soluble, 3=most soluble) (6 pts.) 4. Draw all structural and geometric (cis/trans) isomers resulting from the monochlorination of the compound shown below. Place geometric isomers next to each other and circle them. (NOTE: There must be TWO structures in any circles drawn.) You will be penalized for duplicate structures. (9 points) 5. Place the compounds below in order of increasing acidity. (1=least acidic, 3=most acidic) (6 pts.) branching d boiling point 2 3 I nonpolar polar nonpolar like dissolves like hydrogen