ORGANIC CHEM +SG +SAPLING >IP<
ORGANIC CHEM +SG +SAPLING >IP<
6th Edition
ISBN: 9781319171179
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 18, Problem 18.46AP
Interpretation Introduction

(a)

Interpretation:

The product on reaction of piodotoluene with CH3OH is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as nucleophile. In nucleophilc acyl substitution reaction, nucleophile takes the position of leaving group.

Expert Solution
Check Mark

Answer to Problem 18.46AP

No product is formed on reaction of piodotoluene with CH3OH.

Explanation of Solution

The reaction of piodotoluene with CH3OH is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  1

Figure 1

Aryl iodides cannot undergo nucleophilic substitution reaction. Aryl iodides neither undergo SN2 reaction due to the inability of attack on backside nor do they undergo SN1 reaction as a carbocation cannot be formed.

Conclusion

There is no product formed on reaction of piodotoluene with CH3OH.

Interpretation Introduction

(b)

Interpretation:

The product on reaction of piodotoluene with CH3O in CH3OH is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as nucleophile. In nucleophilc acyl substitution reaction, nucleophile takes the position of leaving group.

Expert Solution
Check Mark

Answer to Problem 18.46AP

No product is formed on reaction of piodotoluene with CH3O in CH3OH.

Explanation of Solution

The reaction of piodotoluene with CH3O in CH3OH is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  2

Figure 2

Aryl iodides cannot undergo nucleophilic substitution reaction. Aryl iodides neither undergo SN2 reaction due to the inability of attack on backside nor do they undergo SN1 reaction as a carbocation cannot be formed.

Conclusion

There is no product formed on reaction of piodotoluene with CH3O in CH3OH.

Interpretation Introduction

(c)

Interpretation:

The product on reaction of piodotoluene with CH3O in presence of pressure and heat is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as nucleophile. In nucleophilc acyl substitution reaction, nucleophile takes the position of leaving group.

Expert Solution
Check Mark

Answer to Problem 18.46AP

No product is formed on reaction of piodotoluene with CH3O.

Explanation of Solution

The product on reaction of piodotoluene with CH3O is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  3

Figure 3

Aryl iodides cannot undergo nucleophilic substitution reaction. Aryl iodides neither undergo SN2 reaction due to the inability of attack on backside nor do they undergo SN1 reaction as a carbocation cannot be formed.

Conclusion

There is no product formed on reaction of piodotoluene with CH3O.

Interpretation Introduction

(d)

Interpretation:

The product on reaction of piodotoluene with Mg in THF is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of piodotoluene with Mg in THF is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  4

Explanation of Solution

The reaction of piodotoluene with Mg in THF is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  5

Figure 4

In the above reaction, magnesium gets inserted in the carbon-halogen bond to form a Grignard reagent. THF is used as the reaction should be done in anhydrous and inert condition. Therefore, the product formed on reaction of piodotoluene with Mg in THF is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  6

Figure 5

Conclusion

The reaction of piodotoluene with Mg in THF is shown in Figure 5.

Interpretation Introduction

(e)

Interpretation:

The product on reaction of the product formed in part (d) with ClSn(CH3)3 is to be stated.

Concept introduction:

Stille reaction is an example of coupling reaction. In Stille reaction, the triflate reacts with trimethylstannane in presence of Pd catalyst and LiCl to give a coupled product of hydrocarbon part of trimethylstannane and triflate.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of the product formed in part (d) with ClSn(CH3)3 is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  7

Explanation of Solution

The product formed in part (d) is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  8

Figure 5

The reaction of the product formed in part (d) with ClSn(CH3)3 is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  9

Figure 6

In the above reaction, a stannane compound is formed on reaction of a Grignard reagent with ClSn(CH3)3. The reaction is known as a Stille coupling reaction. It involves the formation of a carbon-carbon bond. Therefore, the product on reaction of the product formed in part (d) with ClSn(CH3)3 is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  10

Figure 7

Conclusion

The product on reaction of the product formed in part (d) with ClSn(CH3)3 is shown in Figure 7.

Interpretation Introduction

(f)

Interpretation:

The product on reaction of piodotoluene with Li in hexane is to be stated.

Concept introduction:

Alkyl lithium is an organolithium reagent. It contains carbon-lithium bond. It is used in organic synthesis and to transfer an organic group to substrate. Halo compounds on reaction with lithium under inert conditions tend to form carbon-lithium bond. The reaction in which a halo group is lost and a new carbon-lithium bond is formed is known as lithium-halogen exchange reaction.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of piodotoluene with Li in hexane is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  11

Explanation of Solution

The reaction of piodotoluene with Li in hexane is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  12

Figure 8

The above reaction is known as lithium-halogen exchange reaction. The reaction occurs under inert conditions. In this reaction, two moles of lithium react with piodotoluene to form a carbon-lithium bond and one mole of lithium iodide is formed as side product. Therefore, the product formed on reaction of piodotoluene with Li in hexane is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  13

Figure 9

Conclusion

The product on reaction of piodotoluene with Li in hexane is shown in Figure 9.

Interpretation Introduction

(g)

Interpretation:

The product on reaction of piodotoluene with H2C=CH2,Pd(PPh3)4 catalyst, and (Et)3N: in CH3CN is to be stated.

Concept introduction:

The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new CC bond is known as Heck reaction. Generally [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of piodotoluene with H2C=CH2,Pd(PPh3)4 catalyst, and (Et)3N: in CH3CN is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  14

Explanation of Solution

The reaction of piodotoluene with H2C=CH2,Pd(PPh3)4 catalyst, and (Et)3N: in CH3CN is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  15

Figure 10

In the above reaction a coupled product is formed. The coupling takes place between ethene and piodotoluene in presence of Pd(PPh3)4 catalyst and base like (Et)3N:. This reaction is also known as Heck reaction. Therefore, the product formed on reaction of piodotoluene with H2C=CH2,Pd(PPh3)4 catalyst, and (Et)3N: in CH3CN is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  16

Figure 11

Conclusion

The product on reaction of piodotoluene with H2C=CH2,Pd(PPh3)4 catalyst, and (Et)3N: in CH3CN is shown in Figure 11.

Interpretation Introduction

(h)

Interpretation:

The product on reaction of product of part (e) with phenyl triflate, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is to be stated.

Concept introduction:

Stille reaction is an example of coupling reaction. In Stille reaction, the triflate reacts with trimethylstannane in presence of Pd catalyst and LiCl to give a coupled product of hydrocarbon part of trimethylstannane and triflate.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of product of part (e) with phenyl triflate, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  17

Explanation of Solution

The product formed in part (e) is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  18

Figure 7

The reaction of above compound with phenyl triflate, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  19

Figure 12

The above reaction is an example of Stille coupling reaction. In this reaction a triflate reacts with stannane compound in presence of Pd(PPh3)4 as catalyst to give a coupled product. The coupling occurs between triflate and stannane compound to form a biphenyl. Therefore, the product on reaction of product of part (e) with phenyl triflate, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  20

Figure 13

Conclusion

The product on reaction of product of part (e) with phenyl triflate, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown in Figure 13.

Interpretation Introduction

(i)

Interpretation:

The product on reaction of piodotoluene with PhB(OH)2, aqueous Na2CO3, and Pd(PPh3)4 catalyst is to be stated.

Concept introduction:

The Suzuki coupling reaction is a reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a Pd(0) catalysed reaction. This reaction can be used to prepare biaryls, aryl-substituted alkenes, and conjugated alkenes.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of piodotoluene with PhB(OH)2, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  21

Explanation of Solution

The reaction of piodotoluene with PhB(OH)2, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  22

Figure 14

In the above reaction, piodotoluene reacts with phenylboronic acid to form a coupled product. The coupling occurs between phenylboronic acid and piodotoluene to form a new carbon-carbon bond. This results in the formation of a biphenyl. This reaction is known as Suzuki coupling reaction. Therefore, the product on reaction of piodotoluene with PhB(OH)2, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  23

Figure 15

Conclusion

The product on reaction of piodotoluene with PhB(OH)2, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown in Figure 15.

Interpretation Introduction

(j)

Interpretation:

The product on reaction of product of part (d) with B(OCH3)3, then H3O+/H2O is to be stated.

Concept introduction:

The Suzuki coupling reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a Pd(0) catalyzed reaction. This reaction can be used to prepare biaryls, aryl-substituted alkenes, and conjugated alkenes.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product of part (d) with B(OCH3)3, then H3O+/H2O is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  24

Explanation of Solution

The product of part (d) is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  25

Figure 5

The reaction of product of part (d) with B(OCH3)3, then H3O+/H2O is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  26

Figure 16

In the above reaction, ptolylmagnesiumiodide reacts with B(OCH3)3 followed by hydrolysis to give boronic acid. This reaction is an example of Suzuki reaction. Therefore, the product of part (d) with B(OCH3)3, then H3O+/H2O is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  27

Figure 17

Conclusion

The product of part (d) with B(OCH3)3, then H3O+/H2O is shown in Figure 17.

Interpretation Introduction

(k)

Interpretation:

The product on reaction of product of part (j) with (E)1bromopropene, aqueous Na2CO3, and Pd(PPh3)4 catalyst is to be stated.

Concept introduction:

The Suzuki coupling reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a Pd(0) catalysed reaction. This reaction can be used to prepare biaryls, aryl-substituted alkenes, and conjugated alkenes.

Expert Solution
Check Mark

Answer to Problem 18.46AP

The product on reaction of product of part (j) with (E)1bromopropene, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  28

Explanation of Solution

The product of part (j) is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  29

Figure 17

The reaction of product of part (j) with (E)1bromopropene, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  30

Figure 18

The above reaction is Suzuki coupling reaction. In this reaction, ptolylboronicacid reacts with the given alkyne in presence of sodium carbonate and Pd(PPh3)4 catalyst to give a coupled product. Therefore, the product of part (j) with (E)1bromopropene, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 18, Problem 18.46AP , additional homework tip  31

Figure 19

Conclusion

The product on reaction of product of part (j) with (E)1bromopropene, aqueous Na2CO3, and Pd(PPh3)4 catalyst is shown in Figure 19.

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Chapter 18 Solutions

ORGANIC CHEM +SG +SAPLING >IP<

Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Prob. 18.16PCh. 18 - Prob. 18.17PCh. 18 - Prob. 18.18PCh. 18 - Prob. 18.19PCh. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Prob. 18.25PCh. 18 - Prob. 18.26PCh. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Prob. 18.30PCh. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Prob. 18.36PCh. 18 - Prob. 18.37PCh. 18 - Prob. 18.38PCh. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Prob. 18.41PCh. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46APCh. 18 - Prob. 18.47APCh. 18 - Prob. 18.48APCh. 18 - Prob. 18.49APCh. 18 - Prob. 18.50APCh. 18 - Prob. 18.51APCh. 18 - Prob. 18.52APCh. 18 - Prob. 18.53APCh. 18 - Prob. 18.54APCh. 18 - Prob. 18.55APCh. 18 - Prob. 18.56APCh. 18 - Prob. 18.57APCh. 18 - Prob. 18.58APCh. 18 - Prob. 18.59APCh. 18 - Prob. 18.60APCh. 18 - Prob. 18.61APCh. 18 - Prob. 18.62APCh. 18 - Prob. 18.63APCh. 18 - Prob. 18.64APCh. 18 - Prob. 18.65APCh. 18 - Prob. 18.66APCh. 18 - Prob. 18.67APCh. 18 - Prob. 18.68APCh. 18 - Prob. 18.69APCh. 18 - Prob. 18.70APCh. 18 - Prob. 18.71APCh. 18 - Prob. 18.72APCh. 18 - Prob. 18.73APCh. 18 - Prob. 18.74APCh. 18 - Prob. 18.75APCh. 18 - Prob. 18.76APCh. 18 - Prob. 18.77APCh. 18 - Prob. 18.78APCh. 18 - Prob. 18.79APCh. 18 - Prob. 18.80APCh. 18 - Prob. 18.81APCh. 18 - Prob. 18.82APCh. 18 - Prob. 18.83APCh. 18 - Prob. 18.84APCh. 18 - Prob. 18.85APCh. 18 - Prob. 18.86APCh. 18 - Prob. 18.87APCh. 18 - Prob. 18.88APCh. 18 - Prob. 18.89APCh. 18 - Prob. 18.90APCh. 18 - Prob. 18.91APCh. 18 - Prob. 18.92AP
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