Practice First Hour Exam M.A. Walker

150 points total, 50 minutes duration. Fill in the answers directly on to the question sheet.

1. (10 points) Give a systematic name for both of the following compounds.

2. (10 points)[Amended version] Draw the MO's showing the C=N triple bond in H-C=N.

3. (20 points) (a) Show all major resonance forms for phenoxide ion:

(b) Draw the structure of the conjugate acid of phenoxide ion.

(c) What functional groups are present in your answer to (b)?

4. (20 points) In the free radical chlorination of 2-methylpropane there are two possible products, as shown:

The energy diagram for the reaction is shown:

(a) Show the structures of the two intermediates, Int_A and Int_B

(b) Show the activation energy for each reaction, by drawing it on to the above diagram.

(c) Which is the more stable product? Which product forms more quickly?

5. (20 points) Draw an energy curve for the flipping of cyclohexane from one chair to another. Show which minima and maxima correspond to the chairs, half-chairs, twist boats and boat (you need not draw these, merely label them). Which step in the flip is the slowest step?

[Use a separate piece of paper]

6. (10 points) Draw curved arrows to match the electron flow in the following reaction:

6. (30 points) Circle the more stable of each of the following pairs.

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