WS-1.16: Draw the resonance forms of a) an allyl cation and b) an allyl anion.

Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?

Change ethane into 1,2-ethanediol (HOCH2CH2OH) by removing one hydrogen atom from each carbon atom and replacing with a hydroxide (-OH) group.   Draw a Lewis structure for 1,2-ethanediol.

2. Both pairs below show arrangements of the same (fictional) formula: A,X Which pair (a orb) represents resonance structures? Explain. a) A X=A A =X b) A X=A A XEA A

Draw the best Lewis structure for the linear C₁ion, including all lone pair electrons and non-zero formal charges. Click and drag to start drawing a structure. × X :□ P

Convert the condensed formula CH3(CH2), CHO into a Lewis structure (including all lone pair electrons). Click and drag to start drawing a structure. X 5 A

2. For a molecular formula of C5H6O: a) Draw Lewis structures, showing all bonding and non-bonding electrons, for one compound with an alcohol functional group; one with an ether functional group; one with a ketone functional group; and one with an aldehyde functional group. b) For each compound, indicate all bond angles and build a molecular model. c) Indicate whether each pair of valence electrons is non-bonding (n) or σ- or - bonded. For each atom, indicate the corresponding orbitals that are involved (e.g. nsp3, Osp3-sp3, etc.).

4. One of the resonance structures of "tropylium ion" (C7H7*) is shown below. It is planar and aromatic with Hückel number of p-n electrons where n=1. Draw all the other contributing resonance structures. (There are more than two.) Based on the “average" of the contributing resonance structures, how close does the average ring carbon get to its "octeť" in tropylium ion?

#2

Draw out the organic shorthand for the molecules below, and then draw another possible resonance structure of the same molecule next to with arrows to show electron movement.  -CH3CH2CONH3 -CH3CH2COOH