
Organic Chemistry I 

Professor Carl C. Wamser 

Chapter 1 HW Answers 
Carey, pages 50  56:
Problems 1.33  1.40, 1.43  1.50, 1.55  1.65, 1.66, 1.68
1. Write good Lewis structures for the compounds listed below. The structures are written in the standard abbreviated forms, which give some indication about the order in which atoms are bonded.
Indicate the hybridization of each carbon atom and describe the expected geometry. If there are additional contributing resonance forms, show them and indicate whether they contribute equally, or if not, which is the preferred resonance form.
a) CH3OOH
C  sp3
 molecular geometry = tetrahedral
 electron geometry = tetrahedral
b) HCOO
both resonance forms contribute equallyC  sp2
 molecular geometry = trigonal planar
 electron geometry = trigonal planar
c) HCNO
better resonance form
C  sp
 molecular geometry = linear
 electron geometry = linearN  sp
 molecular geometry = linear
 electron geometry = linear
d) CH3CNH+
better resonance form
C(H3)  sp3
 molecular geometry = tetrahedral
 electron geometry = tetrahedralC  sp
 molecular geometry = linear
 electron geometry = linearN  sp
 molecular geometry = linear
 electron geometry = linear
e) CH2OH+
C  sp2
 molecular geometry = trigonal planar
 electron geometry = trigonal planarO  sp2
 molecular geometry = bent
 electron geometry = trigonal planar