1 Chapter 16 Worksheet Key 1. For each compound below, state the number of π-electrons in the conjugated cycle, if any, and state whether the compound is aromatic, antiaromatic, or nonaromatic. 2. non-conj. Pi-system nonaromatic 1.cyclic, planar 2.conj. pisystem 3. 4e- 1. cyclic, planar 2. conj. pisystem 3. 10e- 1. cyclic, planar 2. conj. pisystem 3. 6e- aromatic aromatic antiaromatic 1. cyclic, planar 2. conj. pi-system (as part of the conj. pisystem) 3. 18earomatic (lone pairs on N in plane) 2. no conj. pisystem nonaromatic 1. cyclic, planar 2. conj. pisystem in the benzene part 3. 6e 2. no conj. pisystem 1. cyclic, planar 1. cyclic 2. no conj. pi2. conj. pi-system system 3. 6e nonaromatic nonaromatic aromatic aromatic © John Congleton 2 2. no conj. pisystem 1. cyclic 2. conj. pi-system 3. 10e- in plane 1. cyclic 2. 2 sets of conj. pisystems Aromatic (sides…) 3. 2 sets of 6e- non aromatic aromatic aromatic 1. cyclic, planar 2. conj. pisystem 3. 4e- 1. cyclic but not planar… 2. conj. pisystem 3. 10e- antiaromatic 2. no conj. pi-system 2. no conj. pi-system nonaromatic nonaromatic 1. cyclic, planar 2. conj. pi2.No-conj. sysytem System 3. 6e- 1. cyclic but probably not planar aromatic nonaromatic nonaromatic nonaromatic © John Congleton 3 3. For each compound below, state the number of π-electrons in the conjugated cycle, if any, and state whether the compound is aromatic, antiaromatic, or nonaromatic. Show how the π-electrons are delocalized by drawing all the significant resonance structures for each compound. a. - 6earomatic HN N - + + + HN HN -- N these can't move... HN N N + back to orig. HN N - b. B H H H 4eantiaromatic _ _ B H _ B B + + + H _ B + c. N 10earomatic N N © John Congleton 4 d. + + + + - 2e aromatic in this f orm... e. O O+ 6earomatic -B B O+ -B 4. Draw the following compounds. (a) m-vinylbenzoic acid O OH (b) p-bromophenol OH Br (c) o-(3,5-dinitrophenyl)toluene © John Congleton 5 NO2 toluene 5 6 CH3 4 1 3 2 NO2 (d) 3,4-dichloro-N,N-diethylaniline N Cl Cl © John Congleton
© Copyright 2024