Organic Chemistry, Books a la Carte Edition (9th Edition)
Organic Chemistry, Books a la Carte Edition (9th Edition)
9th Edition
ISBN: 9780134160382
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 6, Problem 6.30SP

(a)

Interpretation Introduction

To determine: The method of conversion of 1-phenylpropane to 1-bromo-1-phenylpropane and unwanted products that might produce undesirable impurities in the product.

Interpretation: The method of conversion of 1-phenylpropane to 1-bromo-1-phenylpropane and unwanted products that might produce undesirable impurities in the product is to be stated.

Concept introduction: NBS is N-bromosuccinimide. It is used as an alternative for Br2. The chemical reaction involved in the replacement of an allylic carbon by bromine is known as allylic bromination. NBS provides low concentration of Br2.

(a)

Expert Solution
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Answer to Problem 6.30SP

The conversion of 1-phenylpropane to 1-bromo-1-phenylpropane is shown in Figure 1.

Explanation of Solution

The conversion of 1-phenylpropane to 1-bromo-1-phenylpropane is shown below.

Organic Chemistry, Books a la Carte Edition (9th Edition), Chapter 6, Problem 6.30SP , additional homework tip  1

Figure 1

In the above reaction, 1-phenylpropane reacts with NBS to form 1-bromo-1-phenylpropane, NBS is N-bromosuccinimide. In benzylic bromination, it acts as bromine source. Benzylic position is next to aromatic ring. NBS provides a consistently low concentration of Br2 which is essential to avoid undesirable products. If concentration of bromine is high, then it will add to the double bonds of aromatic ring to form unwanted products.

(b)

Interpretation Introduction

To determine: The method of conversion of 1-phenylpropane to 1-methoxy-1-phenylpropane and unwanted products that might produce undesirable impurities in the product.

Interpretation: The method of conversion of 1-phenylpropane to 1-methoxy-1-phenylpropane and unwanted products that might produce undesirable impurities in the product is to be stated.

Concept introduction: NBS is N-bromosuccinimide. It is used as an alternative for Br2. The chemical reaction involved in the replacement of an allylic carbon by bromine is known as allylic bromination. NBS provides low concentration of Br2.

(b)

Expert Solution
Check Mark

Answer to Problem 6.30SP

The conversion of 1-phenylpropane to 1-methoxy-1-phenylpropane is shown in Figure 2 and Figure 3.

Explanation of Solution

In first step, 1-phenylpropane reacts with NBS to form 1-bromo-1-phenylpropane as shown below. The mechanism will be predominantly second order (SN2).

Organic Chemistry, Books a la Carte Edition (9th Edition), Chapter 6, Problem 6.30SP , additional homework tip  2

Figure 2

In the second step, 1-bromo-1-phenylpropane reacts with ethoxide ion to form 1-methoxy-1-phenylpropane. The mechanism will be predominantly first order (SN1). 1-bromo-1-phenylpropane is a secondary halide. Undesirable products are formed in SN1 mechanism.

Organic Chemistry, Books a la Carte Edition (9th Edition), Chapter 6, Problem 6.30SP , additional homework tip  3

Figure 3

(c)

Interpretation Introduction

To determine: The method of conversion of 1-phenylpropane to 2-phenylbutanenitrile and unwanted products that might produce undesirable impurities in the product.

Interpretation: The method of conversion of 1-phenylpropane to 2-phenylbutanenitrile and unwanted products that might produce undesirable impurities in the product is to be stated.

Concept introduction: NBS is N-bromosuccinimide. It is used as an alternative for Br2. The chemical reaction involved in the replacement of an allylic carbon by bromine is known as allylic bromination. NBS provides low concentration of Br2.

(c)

Expert Solution
Check Mark

Answer to Problem 6.30SP

The conversion of 1-phenylpropane to 2-phenylbutanenitrile is shown in Figure 2 and Figure 4.

Explanation of Solution

In first step, 1-phenylpropane reacts with NBS to form 1-bromo-1-phenylpropane as shown below. The mechanism will be predominantly second order (SN2).

In the second step, 1-bromo-1-phenylpropane reacts with potassium cyanide to form 2-phenylbutanenitrile. The mechanism will be predominantly first order (SN1). 1-bromo-1-phenylpropane is a secondary halide. Undesirable products are formed in SN1 mechanism.

Organic Chemistry, Books a la Carte Edition (9th Edition), Chapter 6, Problem 6.30SP , additional homework tip  4

Figure 4

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Chapter 6 Solutions

Organic Chemistry, Books a la Carte Edition (9th Edition)

Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
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