
(a)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Alkyl tosylates undergo elimination reaction when they are allowed to react with strong nucleophilic base. The mechanism of the elimination reaction is

Answer to Problem 9.69P
The product of the given reaction is,
Figure 2
Explanation of Solution
The given reaction involves treatment of alkyl tosylate with
Alkyl tosylates undergo elimination reaction when they are allowed to react with strong nucleophilic base. The mechanism of the reaction is
Figure 1
Thus, the product of the given reaction is,
Figure 2
The product of the given reaction is drawn in Figure 2.
(b)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: The reaction of alcohols with halogen acids

Answer to Problem 9.69P
The product of the given reaction is,
Figure 4
Explanation of Solution
The given reaction involves treatment of an alcohol with
The reaction of alcohols with halogen acids
The corresponding reaction is shown below.
Figure 3
Thus, the product of the given reaction is,
Figure 4
The product of the given reaction is drawn in Figure 4.
(c)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Thiols react with

Answer to Problem 9.69P
The product of the given reaction is,
Figure 6
Explanation of Solution
The given reaction involves treatment of thiol with
Thiols react with
The corresponding reaction is shown below.
Figure 5
Thus, the product of the given reaction is,
Figure 6
The product of the given reaction is drawn in Figure 6.
(d)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: The

Answer to Problem 9.69P
The product of the given reaction is,
Figure 8
Explanation of Solution
The given reaction involves treatment of alkyl tosylate with
The
Figure 7
Thus, the product of the given reaction is,
Figure 8
The product of the given reaction is drawn in Figure 8.
(e)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Alkyl bromides are obtained by the reaction of

Answer to Problem 9.69P
The product of the given reaction is,
Figure 10
Explanation of Solution
The given reaction involves treatment of secondary alcohol with
Alkyl bromides are obtained by the reaction of
Figure 9
Thus, the product of the given reaction is,
Figure 10
The product of the given reaction is drawn in Figure 10.
(f)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Alcohols are converted into alkyl tosylates by treatment with

Answer to Problem 9.69P
The product of the given reaction is,
Figure 12
Explanation of Solution
The given reaction involves treatment of an alcohol with
Alcohols are converted into alkyl tosylates by treatment with
Figure 11
Thus, the product of the given reaction is,
Figure 12
The product of the given reaction is drawn in Figure 12.
(g)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: The opening of an

Answer to Problem 9.69P
The product of the given reaction is,
Figure 14
Explanation of Solution
The give reaction involves treatment of an epoxide with halogen acid
The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile
The corresponding reaction is shown below.
Figure 13
Thus, the product of the given reaction is,
Figure 14
The product of the given reaction is drawn in Figure 14.
(h)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile

Answer to Problem 9.69P
The product of the given reaction is,
Figure 16
Explanation of Solution
The give reaction involves treatment of an epoxide with
The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile
The corresponding reaction is shown below.
Figure 15
Thus, the product of the given reaction is,
Figure 16
The product of the given reaction is drawn in Figure 16.
(i)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Ethers are the most common organic products of nucleophilic substitution reaction. They are prepared from alkyl halides and strong nucleophiles. The reaction proceeds through

Answer to Problem 9.69P
The product of the given reaction is,
Figure 18
Explanation of Solution
The given reaction involves treatment of a
The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction,
The obtained alkoxide from this reaction contains
The corresponding reaction is shown below.
Figure 17
Thus, the product of the given reaction is,
Figure 18
The product of the given reaction is drawn in Figure 18.
(j)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Ethers react with strong acids, (only
In this reaction, both

Answer to Problem 9.69P
The product of the given reaction is,
Figure 20
Explanation of Solution
The given reaction involves treatment of an ether with two equivalents of
Ethers react with strong acids, (only
In this reaction, both
The corresponding reaction is shown below.
Figure 19
Thus, the product of the given reaction is,
Figure 20
The product of the given reaction is drawn in Figure 20.
(k)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Sulfides are prepared from thiols by the successive treatment of sodium hydride (a good base), and an alkyl halide. The mechanism of the reaction is

Answer to Problem 9.69P
The product of the given reaction is,
Figure 22
Explanation of Solution
The given reaction involves treatment of an alkyl halide with
The corresponding reaction is shown below.
Figure 21
Thus, the product of the given reaction is,
Figure 22
The product of the given reaction is drawn in Figure 22.
(l)
Interpretation: The product of the given reaction is to be drawn including stereochemistry if appropriate.
Concept introduction: Sulfide involves a nucleophilic sulfur atom. It reacts rapidly with unhindered alkyl halide to form corresponding sulfonium ion. The mechanism of the reaction is

Answer to Problem 9.69P
The product of the given reaction is,
Figure 24
Explanation of Solution
The given reaction involves treatment of sulfide with an unhindered alkyl halide.
Sulfide involves a nucleophilic sulfur atom. It reacts rapidly with unhindered alkyl halide to form corresponding sulfonium ion. The mechanism of the reaction is
The corresponding reaction is shown below.
Figure 23
Thus, the product of the given reaction is,
Figure 24
The product of the given reaction is drawn in Figure 24.
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Chapter 9 Solutions
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