Exam 4 Name ______

CHEM210

a. /
b. /
c. /
d. /
  1. (48 pts) Complete the equations for the following reactions. Show all organic products – if two or more products form, indicate the major product. Indicate proper stereochemistry where necessary.
  2. (8 pts) Mechanism – conversion of ROH to RBr with PBr3 with stereochemical inversion. In the space below show how this conversion occurs using 2-butanol as the starting material with curved arrows for the movement of electrons, proper Lewis structures and formal charges. Be sure to show how the stereochemistry is inverted.
  1. (6 pts) When the following cyclic ether is treated with methanol with a catalytic amount of H2SO4, one of the two products shown is formed quantitatively with only a trace of the other. Which one is the major product? Propose a reaction mechanism to illustrate why.
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / A racemic mixture of I and II
c. / III
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / V
c. / III
  1. What reagent(s) would be the best choice to complete the following reaction?
a. / 1. NaBr; 2. H3O+ / d. / 1. NaBr; 2. HO
b. / Br2 / e. / HBr
c. / PBr3
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / V
c. / III
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / V
c. / III
  1. Which of the following compounds would not produce the same major product as the others when treated with HCl?
a. / A / d. / D
b. / B / e. / E
c. / C
  1. What will be the major product of the reaction below? (TfOH is like TsOH or H2SO4)
a. / / d. /
b. / / e. /
c. /

Exam 4 - KEY Name ______

CHEM210

a. /
b. /
c. /
d. /
  1. (48 pts) Complete the equations for the following reactions. Show all organic products – if two or more products form, indicate the major product. Indicate proper stereochemistry where necessary.
  2. (8 pts) Mechanism – conversion of ROH to RBr with PBr3 with stereochemical inversion. In the space below show how this conversion occurs using 2-butanol as the starting material with curved arrows for the movement of electrons, proper Lewis structures and formal charges. Be sure to show how the stereochemistry is inverted.

  1. (6 pts) When the following cyclic ether is treated with methanol with a catalytic amount of H2SO4, one of the two products shown is formed quantitatively with only a trace of the other. Which one is the major product? Propose a reaction mechanism to illustrate why.

  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / A racemic mixture of I and II
c. / III
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / V
c. / III
  1. What reagent(s) would be the best choice to complete the following reaction?
a. / 1. NaBr; 2. H3O+ / d. / 1. NaBr; 2. HO
b. / Br2 / e. / HBr
c. / PBr3
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / V
c. / III
  1. What is the most likely product of the following reaction?
a. / I / d. / IV
b. / II / e. / V
c. / III
  1. Which of the following compounds would not produce the same major product as the others when treated with HCl?
a. / A / d. / D
b. / B / e. / E
c. / C
  1. What will be the major product of the reaction below? (TfOH is like TsOH or H2SO4)
a. / / d. /
b. / / e. /
c. /