Chem 30B           Mar 15, 2004         Name ________________________

1st hour exam                                                           please print

100 points     Points are in the left margin, e.g., [4]      Seager, Chpts 1-4

 

Some questions have more than one correct answer.

 

1. Give structures for these compounds.                    Draw structures here

a. [4] dichhloroacetaldehyde

 

 

b. [4]   1-phenyl-2-propanol

 

 

  c. [4] trans-2-methylcyclopentanol

 

 

 d. [7] a very water soluble compound with the formula C4H8O2

 

 

2. Give a complete name for

 

a. [5]

       p-t-butylphenol      .

 

 

 b.  [5] 

               ethyl methyl disulfide                              .

 

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4. Draw the structure of the major organic  products of each of the following reactions.

 

a.     [5]      

                                   

 

b. [5]  

     

c. [5]

 

 

 

 

 

 

5. [12] Circle and name all the functional groups in the following compound.

 

 

                                               

 

  1. [8] Label each structure as a hemiacetal or acetal and carefully circle all the atoms which make up that functional group. Place an asterisk (*) on the central carbon atom of the group.

    

 

       _____  hemiacetal  _______               ______  aceta l _____      

 

 

7. [12] Compound A (below) is always in equilibrium with its isomer B which is a cyclic compound . When B is reacted with methanol and a acid catalyst, compound C and water are formed. Draw clear structural formulas for B and C.

 

 

8. [2]  a. Are the following compounds isomers? Yes X   No ___

 

   [2]  b. In the set of compounds above, the one with highest boiling point is b.

    [4]  c. Briefly explain your choice. Draw a clear simple sketch to support your explanation.

 

ONLY THE HYDROXYL GROUP CAN H-BOND TO ANOTHER HYDROXYL. This H-bonding must be from alcohol to alcohol, not to water.

[2]  d. In the set of compounds above, the one with the greatest water solubility is b.

    [4]  e. Briefly explain your choice. Draw a clear simple sketch to support your explanation.

 

 

9. Aldehydes and ketones have very similar structures

    1. [2] Draw the structures of one (generic) aldehyde and one ketone.

 

 

    1. [2]  Aldehydes and ketones  differ in one important kind of chemical reaction.

That reaction is OXIDATION

    1. [3] Draw chemical structures and equations  and use words to briefly describe that reaction.

 

 

 

 

 

    1. [3] Explain what cause that difference in the reaction.

ONLY THE ALDEHYDE HAS THIS C-H BOND.

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