CHEM 2242 Organic Chemistry Exam

ORGANIC CHEMISTRY I (CHEM 2242)                                                                   EXAM #3

OCTOBER 23, 2020 60 POINTS

 

 

 

 

 

 

 

 

 

BEFORE YOU BEGIN, TAKE A MOMENT TO WRITE DOWN HERE TWO THINGS ON THIS EXAM

THAT YOU ARE CONFIDENT THAT YOU UNDERSTAND:

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**TAKE A BREATH**

QUESTION 1: Draw the most stable carbocation that has the formula C5H9+. (5 points)

 

 

 

 

 

 

 

 

 

QUESTION 2: Classify each of the following reactions as substitution, elimination or addition. (8 points)

 

O

F

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Two types of reaction:

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                                                                                                            __________________________ QUESTION 3: Fill in the blanks for the following reactions. (3 points per blank – 18 points)

CH3

H3C

CH3         

OH

CH3                                                                                              CH3

 

QUESTION 4: Predict whether Compound M has a pKa closer to that of 1-butanol or to that of butanoic acid.  Explain your reasoning.  (4 points)

Compound pKa

1-Butanol (C4H10O)

 

16

Butanoic Acid (C4H8O2)

 

4.8
 

Compound M (C4H6O2)

O

H3COH

QUESTION 5: This compound has three possible conjugate bases. Draw each of them. (6 points)

QUESTION 6: Which position on this molecule is the most acidic? Justify your answer. (3 points)

O

H2N

Cl

H HO

QUESTION 7: Draw the conjugate acid and conjugate base in the following reaction.  Which side of the equilibrium is favored? You must explain your reasoning to receive full credit. (4 points)

O O

+                                              ?

F3CCF3 H3CCH3  H H

 

 

 

QUESTION 8: Draw the mechanisms for the following reactions. Show all necessary arrows and intermediates. (4 points each – 12 points)

H                                                               CH3CH3

                                   +      CH3                                                                                                +        CH3

H C             CH3                             H-Br              H3C Br CH3

H3CH3C

O

H3C OH

CH3H3CCH3

H3CCH3

CH3

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