Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
bartleby

Concept explainers

bartleby

Videos

Textbook Question
100%
Book Icon
Chapter 22, Problem 22.50P

Draw the product formed when phenylacetonitrile ( C 6 H 5 CH 2 CN ) is treated with each reagent.

a. H 3 O +

b. H 2 O,  OH

c. [1] CH 3 MgBr; [2] H 2 O

d. [1] CH 3 CH 2 Li; [2] H 2 O

e. [1] DIBAL-H; [2] H 2 O

f. [1] LiAlH 4 ; [2] H 2 O

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with H3O+ is to be drawn.

Concept introduction: Hydrolysis of nitriles in acidic medium converts them to the corresponding carboxylic acids. The reaction involves two parts; that is nucleophilic addition followed by nucleophilic acyl substitution.

Answer to Problem 22.50P

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with H3O+ is

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  1

Explanation of Solution

The given compound is a nitrile.

Hydrolysis of nitriles in acidic medium converts them to the corresponding carboxylic acids. The reaction involves two parts; that is nucleophilic addition followed by nucleophilic acyl substitution. Phenylacetonitrile (C6H5CH2CN) reacts with H3O+ to form phenylacetic acid as depicted below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  2

Figure 1

Conclusion

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with H3O+ is drawn in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with H2O, HO is to be drawn.

Concept introduction: Phenylacetonitrile undergo hydrolysis in basic medium to form corresponding carboxylate ion. The mechanism of the reaction involves two parts. The first part is conversion of nitrile to a 1ο amide. The second part is hydrolysis to convert 1ο amide into carboxylate anion.

Answer to Problem 22.50P

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with H2O, HO is

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  3

Explanation of Solution

The given compound is a nitrile.

Hydrolysis of nitriles in basic medium converts them to the corresponding carboxylate anion. Nitriles react with H2O, HO to form corresponding carboxylate ions. Phenylacetonitrile (C6H5CH2CN) reacts with H2O, HO to form phenylcarboxylate ion as depicted below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  4

Figure 2

Conclusion

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with H2O, HO is drawn in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]CH3MgBr; [2]H2O is to be drawn.

Concept introduction: The Grignard reagents are organometallic compounds having the general formula RMgX where R is an alkyl or aryl group and X is a halogen atom. Nitriles react with both Grignard reagent, and organolithium reagents, followed by hydrolysis to yield ketones. The reaction utilizes R nucleophile to yield desired product.

Answer to Problem 22.50P

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]CH3MgBr; [2]H2O is

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  5

Explanation of Solution

The given compound is a nitrile.

Nitriles react with both Grignard reagent, and organolithium reagents, followed by hydrolysis to yield ketones. The reaction utilizes R nucleophile to yield desired product.

Phenylacetonitrile undergoes Grignard reaction with [1]CH3MgBr;[2]H2O to form 1-phenylpropan-2-one as depicted below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  6

Figure 3

Conclusion

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]CH3MgBr; [2]H2O is drawn in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]CH3CH2Li;[2]H2O is to be drawn.

Concept introduction: Organolithium reagents are organometallic compounds having the general formula RLi where R can be an alkyl or aryl group. They have a carbon-lithium bond and yield similar product as Grignard reaction.

Answer to Problem 22.50P

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]CH3CH2Li;[2]H2O is drawn in Figure 4.

Explanation of Solution

The given compound is a nitrile.

Nitriles react with both Grignard reagent, and organolithium reagents, followed by hydrolysis to yield ketones. The reaction utilizes R nucleophile to yield desired product.

The treatment of phenylacetonitrile with [1]CH3CH2Li;[2]H2O leads to the formation of 1-phenyl-2-butanone as depicted below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  7

Figure 4

Conclusion

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]CH3CH2Li;[2]H2O is drawn in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]DIBAL-H; [2]H2O is to be drawn.

(e)

Concept introduction: DIBAL-H is a selective and a milder reducing agent than LiAlH4. Nitrile compounds are converted to corresponding aldehydes in the presence of milder reducing agents like DIBAL-H, followed by hydrolysis.

Answer to Problem 22.50P

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]DIBAL-H; [2]H2O is

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  8

Explanation of Solution

Diisobutylaluminiumhydride (DIBAL-H) is a selective reducing agent. It readily converts nitriles compounds to corresponding aldehydes. Phenylacetonitrile (C6H5CH2CN) reacts with [1]DIBAL-H; [2]H2O to form phenylacetic acid as depicted below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  9

Figure 5

Conclusion

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]DIBAL-H; [2]H2O is drawn in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]LiAlH4; [2]H2O is to be drawn.

Concept introduction: LiAlH4 is a strong reducing agent. The reaction of a nitrile with [1]LiAlH4; [2]H2O adds two equivalent of H2 across the CN bond to yield primary amines.

Answer to Problem 22.50P

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]LiAlH4; [2]H2O is

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  10

Explanation of Solution

Nitriles react with [1]LiAlH4; [2]H2O to form amines. The overall reaction adds two equivalent of H2 across the CN bond to yield primary amine. Phenylacetonitrile (C6H5CH2CN) reacts with [1]LiAlH4; [2]H2O to form 2-phenyl ethylamine as depicted below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.50P , additional homework tip  11

Figure 6

Conclusion

The product formed from the treatment of phenylacetonitrile (C6H5CH2CN) with [1]LiAlH4; [2]H2O is drawn in Figure 6.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
None
Unshared, or lone, electron pairs play an important role in determining the chemical and physical properties of organic compounds. Thus, it is important to know which atoms carry unshared pairs. Use the structural formulas below to determine the number of unshared pairs at each designated atom. Be sure your answers are consistent with the formal charges on the formulas. CH. H₂ fo H2 H The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is HC HC HC CH The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is
Draw curved arrows for the following reaction step. Arrow-pushing Instructions CH3 CH3 H H-O-H +/ H3C-C+ H3C-C-0: CH3 CH3 H

Chapter 22 Solutions

Organic Chemistry-Package(Custom)

Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Problem 22.15 Draw the products of each...Ch. 22 - Problem 22.16 Draw the products of each reaction. ...Ch. 22 - Prob. 22.17PCh. 22 - Problem 22.18 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.19PCh. 22 - Problem 22.20 Fenofibrate is a...Ch. 22 - Problem 22.21 What product is formed when the...Ch. 22 - How would you synthesize olestra from sucrose? Ch. 22 - What is the composition of the soap prepared by...Ch. 22 - Problem 22.24 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.25PCh. 22 - Problem 22.26 Some penicillins cannot be...Ch. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Problem 22.30 Glucosamine is a dietry supplement...Ch. 22 - Draw the products of each reaction. a. c. b.Ch. 22 - Draw a tautomer of each compound.Ch. 22 - Draw the product of each reaction. a.b.Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Prob. 22.35PCh. 22 - Problem 22.36 Outline two different ways that can...Ch. 22 - 22.37 Rank the following compounds in order of...Ch. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - Prob. 22.40PCh. 22 - Give thestructure corresponding to each name. a....Ch. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - 22.43 Explain why is a stronger acid and a weaker...Ch. 22 - Draw the product formed when pentanoyl chloride...Ch. 22 - Draw the product formed when pentanoic anhydride...Ch. 22 - Draw the product formed when phenylacetic acid is...Ch. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Draw the product formed when phenylacetonitrile ...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Prob. 22.54PCh. 22 - Prob. 22.55PCh. 22 - Prob. 22.56PCh. 22 - Draw a stepwise mechanism for each reaction. a. b.Ch. 22 - When acetic acid CH3COOH is treated with a trace...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - Prob. 22.62PCh. 22 - Prob. 22.63PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - 22.63 Acid-catalyzed hydrolysis of forms compound...Ch. 22 - Prob. 22.66PCh. 22 - Devise a synthesis of each compound using...Ch. 22 - Convert 1-bromohexane (CH3CH2CH2CH2CH2CH2Br) into...Ch. 22 - Prob. 22.69PCh. 22 - Prob. 22.70PCh. 22 - Prob. 22.71PCh. 22 - Prob. 22.72PCh. 22 - Prob. 22.73PCh. 22 - Prob. 22.74PCh. 22 - Devise a synthesis of each labeled compound using...Ch. 22 - 22.70 What polyester or poly amide can be prepared...Ch. 22 - 22.71 What two monomers are needed to prepare each...Ch. 22 - Prob. 22.78PCh. 22 - How can IR spectroscopy be used to distinguish...Ch. 22 - Rank the compounds in each group in order of...Ch. 22 - 22.75 Identify the structures of each compound...Ch. 22 - 22.76 Identify the structures of A and B, isomers...Ch. 22 - Prob. 22.83PCh. 22 - 22.78 Identify the structure of compound C...Ch. 22 - 22.79 Identify the structures of D and E, isomers...Ch. 22 - 22.80 With reference to amides A and B, the...Ch. 22 - Prob. 22.87PCh. 22 - Prob. 22.88PCh. 22 - Prob. 22.89PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Draw a stepwise mechanism for the following...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License