Organic Chemistry 1 (CHEM313)—Worksheet 01 1. For each of the following compounds, draw the complete Lewis Structure and categorize each bond as (a) non-polar covalent, (b) polar covalent, (c) ionic. If the compound is polar covalent, indicate the direction of the dipole moment, using the symbols d+ and d-. CH4 H3CBr H3CH2COH H2 S 2. Draw the Lewis Structure with formal charges on the atoms that possess the formal charge of the following: BCl4— H3O+ SO42— CH3+ 3. Convert the following condensed formulas into bond-line structures, making sure to draw in zig-zag formation. CH3CH2CH2CH2CH2CH2CH2CH3 FCH2CH2I H2C=CHCH2OH (CH3)2CHCOOH 4. Convert the following into line-bond formula, indicating all lone pairs. H H H H C C H C H C C H H H H H C H H C C N H C H N C C C H C C Cl H H H H C C H O 5. Identify the hybridization (sp, sp2, sp3) of each carbon atom in the following molecule. 6. Identify the number of s bonds, p bonds, lone pairs, and hydrogens in the following molecules. O N N N O N H N _____ s _____ s _____ p _____ p _____ lp _____ lp _____ H _____ H 7. Redraw the structure below filling in all of the carbon atoms and hydrogen atoms. N 8. The following are the reagent, intermediate, and product in a reaction you will learn later in Organic Chemistry. a. b. c. d. Identify any formal charges that are missing from the structures. Determine the hybridization of the central carbon atom of each molecule. Draw in all lone pairs. Redraw the structures with all hydrogen atoms. Cl OH 2 9. Rank the following molecules in order from highest boiling point temperature to highest boiling point temperature. O OH O O- Na+ OH A OH OH OH E Highest bp B C O O F D G H Lowest bp 10. Propan-1-ol (CH3CH2CH2OH) and methyl ethyl ether (CH3OCH2CH3) have the same molecular formulas but different bonding (constitutional isomers). These two molecules have drastically different boiling points: 97.5 oC for propan-1-ol and 45.32 oC for methyl ethyl ether. Draw the Lewis structure of each molecule. Explain the difference in the boiling points of these molecules, using intermolecular forces. (1—3 complete sentences)