Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
bartleby

Concept explainers

Question
Book Icon
Chapter 18, Problem 18.24P

(a)

Interpretation Introduction

Interpretation:

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

Concept introduction:

The reaction of alkyl halides with sodium cyanide gives alkyl cyanides or nitriles. After the reaction there is increase incarbon atoms of the alkyl chain of alkyl halide. The nitriles obtained undergo hydrolysis reaction in presence of acid gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as,

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  1

The hydrolysis reaction of alkyl nitrile in presence of acid is written as,

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  2

The amide is first formed when the cyano group is hydrolysed in excess of water and if there is only one mole of water per mole of nitrile, the reaction can be stopped by the formation of amide.

(b)

Interpretation Introduction

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

Concept introduction:

The reaction of alkyl halides with sodium cyanide gives alkyl cyanides or nitriles. After the reaction there is increase incarbon atoms of the alkyl chain of alkyl halide. The nitriles obtained undergo hydrolysis reaction in presence of acid gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as,

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  3

The hydrolysis reaction of alkyl nitrile in presence of acid is written as,

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  4

The amide is first formed when the cyano group is hydrolysed in excess of water and if there is only one mole of water per mole of nitrile, the reaction can be stopped by the formation of amide.

(c)

Interpretation Introduction

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

Concept introduction:

Amide hydrolysis in aqueous base:

A carboxylate anion and ammonia or an amine will be the product of nitrile hydrolysis in aqueous base.

The formed carboxylate anion can be converted into carboxylic acid by the acidification of the reaction mixture.

(d)

Interpretation Introduction

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

Concept introduction:

Concept introduction:

LiAlH4 is a powerful reducing agent which reduces the cyano group of a nitrile to a primary amino group.

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  5

Blurred answer
Students have asked these similar questions
The odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate)     (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender     (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester.     (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).
The analgesic Tylenol is often taken by people who are allergic to aspirin. Tylenol contains acetaminophen (structure shown) as the active ingredient.   Is the structure of acetaminophen similar to the structure of aspirin? In what way? Would acetaminophen give a positive phenol test? What products would be obtained if acetaminophen were hydrolyzed in acidic aqueous solution?
Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) aniline

Chapter 18 Solutions

Organic Chemistry

Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
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:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning