Chem 143 Problem Set 3 Friday 17th September 2010 1 Draw a line bond structure for each of the following compounds O a CH3C O OCH2CH3 O b CH3CH CHC CCH3 c H H H C H H C C H H C C C H H C H H H 1 2 Write the molecular formula for the following compound O N H C12H19NO 3 Identify the hybridization of the highlighted atoms in the following structures SH a 3 sp sp3 O H3N 2 sp3 as drawn really sp2 sp O homocysteine sp3 b sp3 sp2 camphor 4 Add formal charges to the following compounds a b c H d O 2 N Br H 2 Circle and name the functional groups in the following molecules Cl ether 2 alcohol O OH N H2N carboxylic acid thioether O 2 amide alkene S O N H COOH 1 amine O O 3 amine 2 alkyl halide ketone alkyne ester nitrile CN 5 Draw as many constitutional isomers as you can for C3H6O O O O O O OH O 6 Label the hybridization of the indicated atoms in the following molecule sp2 O N N sp O 2 O HN S N sp2 N sp2 O sp3 sp3 sildenafil Viagra 3 sp3 N 7 What is the molecular formula of sildenafil C22H30N6O4S 8 Draw the following molecules as bond line structures a CH3 2CCHCHCHC CH3 CHCHCHC CH3 CHCH3 b CH2C CH3 CCCH2CHO O 9 Draw bond line structures for CH3CH Cl CH Cl CH3 and CH3CH2CH Cl CH2Cl and predict which has the higher boiling point Cl Cl Cl Cl The structure on the left has no net dipole moment so it has the lower boiling point 118 C vs 125 C for the structure on the right 10 For the following molecules indicate which you expect to be soluble in water polar solvent or hexane apolar solvent COOH O COOH OH OH HO HO COOH water water hexane hexane O 4 water