1. Principles & Modern Applications
General Chemistry
Principles & Modern Applications
9th Edition
Petrucci/Herring/Madura/Bissonnette
Chapter 27
Reactions of Organic Compounds
Dr. Wendy Pell
University of Ottawa
Copyright © 2011 Pearson Canada Inc.

2. Identify the substitution reaction (s) from those listed below:
ethanol in sulphuric acid producing ethene;
methanol in acid producing dimethyl ether;
chlormethane and aqueous NaOH producing methanol and aqueous NaCl
Ethene and hydrogen in the presence of a Pt catalyst produces ethane.
The substitution reaction(s) is(are): B C
A,B
B,C
D,B
Slide 2 of 33

3. Identify the substitution reaction (s) from those listed below:
ethanol in sulphuric acid producing ethene;
methanol in acid producing dimethyl ether;
chlormethane and aqueous NaOH producing methanol and aqueous NaCl
Ethene and hydrogen in the presence of a Pt catalyst produces ethane.
The substitution reaction(s) is(are): B C
A,B
B,C
D,B
Slide 3 of 33

4. Does the nucleophilic substitution of OH- for I- in (S)-2-iodobutane yielding (R)-2-butanol occur via an
SN1
SN2
mechanism ?
Slide 4 of 33

5. Does the nucleophilic substitution of OH- for I- in (S)-2-iodobutane yielding (R)-2-butanol occur via an
SN1
SN2
mechanism ?
Slide 5 of 33

6. Identify the nucleophile in the following substitution reaction occurring in water:
CH3Cl + NaOH  CH3OH + NaCl
1. CH3Cl
2. Cl-
3. CH3OH
4. OH-
5. NaOH
6. NaCl
Slide 6 of 33

7. Identify the nucleophile in the following substitution reaction occurring in water:
CH3Cl + NaOH  CH3OH + NaCl
1. CH3Cl
2. Cl-
3. CH3OH
4. OH-
5. NaOH
6. NaCl
Slide 7 of 33

8. Consider the nucleophilic substitution of Br- by Cl- in the series of compounds to the right.
If the reaction proceeds via an SN2 mechanism, predict the order of increasing rate of reaction. A) B) C) D)
A < B < C < D
D < C < B < A
B < C < D < A
A < D < C < B
Slide 8 of 33

9. Consider the nucleophilic substitution of Br- by Cl- in the series of compounds to the right.
If the reaction proceeds via an SN2 mechanism, predict the order of increasing rate of reaction. A) B) C) D)
A < B < C < D
D < C < B < A
B < C < D < A
A < D < C < B
Slide 9 of 33

10. Consider the nucleophilic substitution of Br- by OH- occurring in an aqueous solution for the series of compounds to the right.
If the reaction proceeds via an SN1 mechanism, predict the order of increasing rate of reaction. A) B) C) D)
A < B < C < D
D < C < B < A
B < C < D < A
A < D < C < B
Slide 10 of 33

11. Consider the nucleophilic substitution of Br- by OH- occurring in an aqueous solution for the series of compounds to the right.
If the reaction proceeds via an SN1 mechanism, predict the order of increasing rate of reaction. A) B) C) D)
A < B < C < D
D < C < B < A
B < C < D < A
A < D < C < B
Slide 11 of 33

12. When water is added across the double bond in 1-butene, which of the following is the major product?1. 2. 3. 4. 5.
Slide 12 of 33

13. When water is added across the double bond in 1-butene, which of the following is the major product?1. 2. 3. 4. 5.
Slide 13 of 33

14. Which of the following, when treated with Cr2O72- in acidic solution, will produce 3-methyl-2-pentanone? 1. 2. 3. 4. 5.

15. Which of the following, when treated with Cr2O72- in acidic solution, will produce 3-methyl-2-pentanone? 1. 2. 3. 4. 5.

16. Ethyl butanoate is an ester which has the smell of pineapple
Ethyl butanoate is an ester which has the smell of pineapple. Which combination of reactants will, when heated in the presence of acid, produce ethyl butanoate?
1. Butanol and ethanol.
Ethyl butanoate
2. Butanoic acid and acetic acid.
3. Butanoic acid and ethanol.
4. Butanol and acetic acid.

17. Ethyl butanoate is an ester which has the smell of pineapple
Ethyl butanoate is an ester which has the smell of pineapple. Which combination of reactants will, when heated in the presence of acid, produce ethyl butanoate?
1. Butanol and ethanol.
Ethyl butanoate
2. Butanoic acid and acetic acid.
3. Butanoic acid and ethanol.
4. Butanol and acetic acid.

18. Which of the compounds below would be produced from the reactants in the box to the right?

19. Which of the compounds below would be produced from the reactants in the box to the right?

20. The major product of the reaction depicted to the right is:
Cl2
FeCl3 1. 2. 3. 4. 5.

21. The major product of the reaction depicted to the right is:
Cl2
FeCl3 1. 2. 3. 4. 5.

22. Consider the substitution reaction of an aromatic with one substituent group as shown to the right.
If X is the NH2 group and Y is OH group, in which position(s) will the OH group be directed ?
ortho
para
ortho and para
meta
no discrimination, a mixture of all products will results

23. Consider the substitution reaction of an aromatic with one substituent group as shown to the right.
If X is the NH2 group and Y is OH group, in which position(s) will the OH group be directed ?
ortho
para
ortho and para
meta
no discrimination, a mixture of all products will results

24. Consider the substitution reaction of an aromatic with two substituent group as shown to the right.
If X is the OH group and Y is Cl, in which position(s) will an incoming group be directed ?
ortho and para to OH
ortho and para to Cl
meta relative to OH
meta relative to Cl
no discrimination, a mixture of all products will results

25. Consider the substitution reaction of an aromatic with two substituent group as shown to the right.
If X is the OH group and Y is Cl, in which position(s) will an incoming group be directed ?
ortho and para to OH
ortho and para to Cl
meta relative to OH
meta relative to Cl
no discrimination, a mixture of all products will results

26. Consider the substitution reaction of an aromatic with two substituent group as shown to the right.
If X is the COOH group and Y is CN group, in which position(s) will an incoming group be directed ?
ortho and para to COOH
ortho and para to CN
meta relative to COOH
meta relative to CN
no discrimination, a mixture of all products will results

27. Consider the substitution reaction of an aromatic with two substituent group as shown to the right.
If X is the COOH group and Y is CN group, in which position(s) will an incoming group be directed ?
ortho and para to COOH
ortho and para to CN
meta relative to COOH
meta relative to CN
no discrimination, a mixture of all products will results

28. (an aldehyde, R=H or alkyl)
Which of the following reactions will most likely produce an aldehyde? R
(an aldehyde, R=H or alkyl)

29. (an aldehyde, R=H or alkyl)
Which of the following reactions will most likely produce an aldehyde? R
(an aldehyde, R=H or alkyl)

30. The rate law for the reaction of the compound to the right with chloride ion was found to be:
Which of the statements below is correct?
1. The mechanism for the reaction is SN1
2. The name of the product is (S)-2-chloro-2-bromobutane.
3. The name of the product is (R)-2-chloro-2-butanol.
4. A racemic mixture of R and S enantiomers will be produced.
5. None of the above statements are correct.

31. The rate law for the reaction of the compound to the right with chloride ion was found to be
Which of the statements below is correct?
1. The mechanism for the reaction is SN1
2. The name of the product is (S)-2-chloro-2-bromobutane.
3. The name of the product is (R)-2-chloro-2-butanol.
4. A racemic mixture of R and S enantiomers will be produced.
5. None of the above statements are correct.

32. Which of the following monomers are likely to polymerize via an step-reaction polymerization mechanism ? A. B. C. D.
A only 4. D only
A and B 5. A and C
C only 6. B only

33. Which of the following monomers are likely to polymerize via an step-reaction polymerization mechanism ? A. B. C. D.
A only 4. D only
A and B 5. A and C
C only 6. B only