CHM 231 – Exam Two

 

The exam consists of 25 multiple choice questions.  For each question there is one and only one best answer.  That answer is the one you should provide.  The final page is a periodic chart.  Turn in only the answer key.  You can take the actual exam questions with you.

 

 

  1. The following reaction is an example of:

 

 

    1. Substitution
    2. Elimination
    3. Addition

 

 

  1. Of the following groups attached to a benzene ring, which would be meta directing?
    1. –Br
    2. –OH
    3. –CH3
    4. –NO2

 

  1. Which of the following chlorides should undergo SN2 reaction fastest?

 

 

 

  1. In the following structure, several hydrogens are labeled.  What is the label on the hydrogen most easily eliminated in an E1 reaction?

 

 

 

 

  1. The best name of the following compound is:

 

 

    1. o-bromo phenol
    2. o-hydroxy bromobenzene
    3. m-bromo phenol
    4. m-hydroxy bromobenzene
    5. p- hydroxyphenol

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

  1. Which of the following structures are chiral ?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

  1. What is the major product of the following SN2 reaction (Fischer projections)?

 

 

  1. The relationship of the following two compounds drawn in Fischer projection is:

 

 

    1. identical structures
    2. diastereomers
    3. enantiomers
    4. skeletal isomers

 

 

 

 

 

 

 

 

 

 

  1. The major product of the following reaction is:

 

 

 

  1. The best starting material for the following reaction is:

 

 

 

  1. The following Fischer projection shows a compound with:

 

 

    1. One chiral center configuration R
    2. One chiral center configuration S
    3. Two chiral centers configurations both R
    4. Two chiral centers configurations one R one S
    5. Two chiral centers configurations both S

 

For the next two questions consider the following structures:

 

 

  1. Which of the above would afford a single product upon monobromination?

 

 

  1. Starting with compound A, which of the others would be the most difficult to make?

 

 

 

 

 

 

 

 

 

 

 

 

  1. The mechanism of the following reaction must be:

 

 

    1. E2
    2. E1
    3. SN2
    4. SN1

 

  1. The following reaction would yield for the product:

 

 

 

 

 

  1. Free radical monochlorination of the compound below would give how many positional isomers?

 

 

    1. One
    2. Two
    3. Three
    4. Four
    5. Five

 

For the following two questions, consider the following energy diagram:

 

 

  1. The intermediate in the above reaction is the energy state with which label?

 

 

  1. The transition state in the rate determining step has which label?

 

 

 

 

  1. To accomplish the following transformation, which of the following sequences is best?

 

 

  1. Reaction of cyclohexene under which conditions below gives a racemic mixture?

 

    1. Reaction with bromine
    2. Hydrogenation (H2 and a catalyst)
    3. Treatment with osmium tetroxide (OsO4)
    4. Reaction with HBr
    5. None of the above gives a racemic mixture

 

 

 

 

 

 

 

 

 

 

 

 

 

  1. Which of the following is least likely to be formed in the following reaction?

 

 

 

  1. The major product of the following E1 reaction should be:

 

 

 

 

 

 

  1. The best starting material to make the following compound is:

 

  1. The following compound can be made by the ozonolysis of:

 

 

    1. cyclohexene
    2. cyclobutene
    3. cyclopentene
    4. benzene

 

  1. The number of possible stereoisomers of the following structure is:

 

 

    1. Two
    2. Three
    3. Four
    4. Eight