Chem 212Survey of Organic and BiochemistrySpring 2005

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Print your full name legibly in the space above.

Exam 1: Ch. 1-5

1 March 2005

Instructions:

1. If you leave the room for any reason you may not return to continue the exam.

2. No books or notes of any kind are permitted. You may borrow a model kit.

3. Put all your answers on this exam paper. If you want something graded which is written on scratch paper, you must indicate so in the regular space for the answer.

Good Luck!

  1. Draw a reasonable Lewis structure for each of the following, showing all lone pairs and formal charges where relevant:
  2. CO32- carbonate anion
  1. CH3CH2+ ethyl cation
  1. HONO
  1. State whether the structures in each pair below are identical, constitutional isomers, cis-trans isomers, or not related.
  1. Answer the following questions about the structure below.
  1. How many hydrogen atoms are in the structure? ______
  2. On the structure above, indicate with an arrow one bond which can freely rotate around 360°.
  3. Circle and name one functional group in the molecule.
  4. Use the VSEPR method to predict the geometry around each of the following atoms (linear, triangular planar, tetrahedral, triangular bipyramidal, octahedral)

C1 C6

C2 C7

C3 C10

  1. Give approximations for the following bond angles:

H-O-C C4-C5-C6

C10-C6-C7 C1-C2-C3

  1. Label the following atoms as primary (1°), secondary (2°), tertiary (3°), or quaternary (4°):

C3 C9

C4 C10
5. Using the following template, draw a Newman projection for 1,1-dichloro-2-methylbutane looking down the C1-C2 bond:

6. Give the chemical name for the following molecules:

7. Next to each name, draw the correct structure for these molecules.

1,4-Butanediol

2-Methyl-2-propyl-1,3-propanediol

3,3-Dimethylcyclohexanethiol

p-Methyl anisole

o-Chloro toluene

2-Bromo-1-ethyl-4-nitrobenzene

trans-2-Methyl-3-hexene

9. Draw a line angle structure for the following molecules:

  1. C5H8, with an alkene (may have other functional groups as well)
  1. C8H14O2, with an ester (may have other functional groups as well)
  1. C7H16O with a tertiary alcohol (may have other functional groups as well)

10. Draw the structure of the starting materials and the organic products for each of the following reactions:

  1. 1-Methylcyclohexene treated with bromine
  1. Ethylcyclohexane treated with bromine and light
  1. 1,4-Dichlorobenzene treated with fuming sulfuric acid (H2SO4)
  1. Benzene treated with bromine and FeBr3
  1. 1-Pentene treated with HCl
  1. 1-Octene treated with water and sulfuric acid (H2SO4)
  1. 2-Propanol treated with chromic acid (K2Cr2O7)
  1. 4-Methyl phenol treated with sodium hydroxide (NaOH)

11. Explain why the boiling point of 1,2-ethanediol (198 ºC) is so much higher than that of 1-propanol (97 ºC) even though their molecular weights are about the same.

12. Both 2,6-Diisopropylcyclohexanol and an intravenous anesthetic Propofol are insoluble in water. Show how these two compounds can be distinguished by their reaction with aqueous sodium hydroxide.

13. Show how to prepare 2-Methyl-2-propanol from 2-methyl-1-propanol.

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