Total 100 points Name

1. Lewis structures. Add the remaining valence electrons to complete the Lewis structures for the following skeletons. Avoid formal charges.

2 Formal charges. Calculate the formal charge for all the atoms other than H:(Don't draw any more electrons)

3 Resonance. Draw a resonance form for the following:

(a)

(b)

4 Molecular structure:

Predict the bond angles and hybridization of asterisked (*) for the molecule below:

(a) /_ H-C*-C (b) /_C-C*-N (c) /_C-N*-H .

hybridization: .

(b) Circle all the cyclohexane rings

cholesterol

(c) What is the molecular formula for a linear alkane that has 25 C's?

(d) What is the molecular formula for a cyclic alkane that has 12 C's?

5 Functional groups.

Circle and identify the functional groups in the next two structures:

(a) (b)

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6 Draw proper organic molecules (correct bonds), which contain the following functional groups:

(a) alcohol (b) amide (c) ester (d) aldehyde

Draw a proper organic molecule that has

(a) one 2°C and two 1°C (b) a 4° carbon

7 Which compounds have the highest boiling points? Why?

(a) 3-methylpentane or n-hexane

(b) octane or propane

8 When hydrocarbons CnHm are combusted for heat or energy, what are the products?

One of these products is thought to cause environmental danger? Which product? What is the danger?

9 Name the following structures:

9b Draw the following molecules:

(a) 3-heptyne (b) 2-ethyl-3-propyl-3-heptene (c) cis-1,4-dimethylcyclohexane

(c) sec-butylcyclopropane (d) 4-isopropyloctane (e) E-1-bromo-2-chloro-1-pentene

10 Name and draw the Newman projections important conformations of propane. Which one is less stable and why?

Draw the most and least stable chair forms of 1,2-dimethylcyclohexane. Label most and least stable.