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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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.

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

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

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

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

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

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

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

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

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

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

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

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

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.

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.

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

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