Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Textbook Question
Chapter 22, Problem 5RQ

What functional group distinguishes each of the following hydrocarbon derivatives?

a. halohydrocarbons

b. alcohols

c. ethers

d. aldehydes

e. ketones

f. carboxylic acids

g. esters

h. amines

Give examples of each functional group. What prefix or suffix is used to name each functional group? What are the bond angles in each? Describe the bonding in each functional group. What is the difference between a primary, secondary, and tertiary alcohol? For the functional groups in a–h, when is a number required to indicate the position of the functional group? Carboxylic acids are often written as RCOOH. What does —COOH indicate and what does R indicate? Aldehydes are sometimes written as RCHO. What does —CHO indicate?

(a)

Expert Solution
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Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

To determine: The functional groups that distinguishes the given hydrocarbon derivatives and the answers for the questions asked.

The functional group that distinguishes halohydrocarbons.

Explanation of Solution

Explanation

The functional group present in halohydrocarbons is halogen

The hydrocarbons are the organic compounds that contain hydrogen and carbon. When halogen is attached to any hydrocarbon, then the compound is known as halohydrocarbons.

Chloropropane is an example of halohydrocarbon where the functional group “chlorine” is attached to the hydrocarbon propane. Structure of halohydrocarbon is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  1

Figure 1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

To determine: The functional group that distinguishes alcohols.

Explanation of Solution

Explanation

The functional group present in alcohols is (-OH) group

When the functional group (-OH) is attached to the hydrocarbons, the compound is known as alcohols. The example of alcohol is propanol. Structure of propanol is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  2

Figure 2

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

To determine: The functional group that distinguishes ethers.

Explanation of Solution

Explanation

The functional group present in ethers is (-O-) group.

In ethers, the oxygen atom is bonded with two alkyl or aryl group. The example of ether is diethylether. Structure of diethylether is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  3

Figure 3

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

To determine: The functional group that distinguishes aldehydes.

Explanation of Solution

Explanation

The functional group present in aldehyde is (-CHO) group.

In aldehydes, the hydrocarbon is attached to (-CHO) group. The example of aldehyde is propanal. Structure of propanal is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  4

Figure 4

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

Explanation of Solution

Explanation

The functional group present in ketones is (C=O) group.

In ketones, the hydrocarbon is attached to (C=O) group. The example of ketone is propan- 2 -one. Structure of propan- 2 -one is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  5

Figure 5

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

Explanation of Solution

Explanation

To determine: The functional group that distinguishes carboxylic acid.

The functional group present in carboxylic acids is (COOH) group.

In carboxylic acids, the hydrocarbon is attached to (COOH) group. The example of carboxylic acid is propanoic acid. Structure of propanoic acid is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  6

Figure 6

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

Explanation of Solution

Explanation

To determine: The functional group that distinguishes esters.

The functional group present in esters is (-COO-) group.

When hydrogen of the carboxylic group is replaced by hydrocarbon group the formation of ester (RCOOR) takes place. The example of ester is ethylpropanoate. Structure of ethylpropanoate is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  7

Figure 7

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

Explanation of Solution

Explanation

To determine: The functional group that distinguishes amines.

The functional group present in amines is (NH2) group.

In amines, (NH2) group is attached to hydrocarbons. The example of amine is methylamine. Structure of methylamine is,

Chemistry, Chapter 22, Problem 5RQ , additional homework tip  8

Figure 8

(II)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation: The given hydrocarbon derivatives are to be distinguished on the basis of functional groups present. Various question based upon the functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

To determine: The answers of the various questions based upon functional groups.

Explanation of Solution

Explanation

Example of each functional group is given below.

The examples of each functional group is,

  1. a) Halohydrocarbon: Chloropropane.
  2. b) Alcohols: propanol.
  3. c) Ethers: diethylether.
  4. d) Aldehydes: propanal.
  5. e) Ketones: propan- 2 -one.
  6. f) Carboxylic acids: propanoic acid.
  7. g) Esters: ethylpropanoate.
  8. h) Amines: methylamine.

Prefixes and suffixes for each functional group are given below.

Prefixes and suffixes for each functional group are,

  1. a) Halohydrocarbon: Prefix “halo”.
  2. b) Alcohols: Suffix “ol”.
  3. c) Ethers: Suffix “oxy”.
  4. d) Aldehydes: Suffix”al”.
  5. e) Ketones: Suffix “one”.
  6. f) Carboxylic acids: Suffix “oic acid”.
  7. g) Esters: Suffix “oate”.
  8. h) Amines: Suffix”amine”.

Bond angles in each of the functional group are,

  1. a) Halohydrocarbon: 109.5° .
  2. b) Alcohols: 109.5° .
  3. c) Ethers: 110°
  4. d) Aldehydes: 120° .
  5. e) Ketones: 120° .
  6. f) Carboxylic acids: 120° .
  7. g) Esters: 120° .
  8. h) Amines: 109.5° .

The bonding in each functional group and the difference between primary, secondary and tertiary alcohol have been rightfully described.

Halohydrocarbons have tetrahedral geometry. Halogen (F,Cl,Br,I) is bonded covalently to a sp3 hybridized carbon.

In alcohols, the oxygen atoms are sp3 hybridized and have bent shape with bond angles less than 109.5° to each other. Alcohols are polar. When the carbon having the alcohol group is attached to only one alkyl group, then the alcohol is known as primary alcohol. When the carbon having the alcohol group is attached to two alkyl groups, then the alcohol is known as secondary alcohol. When the carbon having the alcohol group is attached to three alkyl groups, then the alcohol is known as tertiary alcohol.

The geometry of ethers is tetrahedral, i.e., oxygen is sp3 hybridized. The C0C angle is 110° . The CO bonds are slightly polar.

In aldehydes and ketones, both the carbon and oxygen are sp2 hybridized and the bond angle is 120° .

In carboxylic acids, the carbon and oxygen in the carbonyl group are both sp2 hybridized which gives basic trigonal shape to carbonyl group. The hydroxyl oxygen is also sp2 hybridized which allows one of its lone pair to conjugate with the pi system of the carbonyl group. This makes the carboxyl group planar.

In esters, the CCO bond angle is 120° . In amines, the nitrogen is sp3 hybridized and the bond angle between NH bonds is 109.5° .

The significance of R and COOH in carboxylic acid and R and CHO in aldehydes have been rightfully stated.

The carboxylic acids are identified by the formula RCOOH .

The R indicates the alkyl or aryl group attached to the carboxylic acids.

The COOH indicates the carboxylic acid functional group.

The aldehydes are identified by the formula RCHO .

The R indicates the alkyl or aryl group in the aldehydes.

The CHO indicates the aldehyde functional group.

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Chapter 22 Solutions

Chemistry

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Name...Ch. 22 - Prob. 154CWPCh. 22 - Prob. 155CWPCh. 22 - Prob. 156CWPCh. 22 - Prob. 157CPCh. 22 - Estimate H for the following reactions using bond...Ch. 22 - Prob. 159CPCh. 22 - Prob. 160CPCh. 22 - Prob. 161CPCh. 22 - Consider a sample of a hydrocarbon at 0.959 atm...Ch. 22 - Prob. 163CPCh. 22 - Prob. 164CPCh. 22 - Prob. 165CPCh. 22 - Prob. 166CPCh. 22 - Prob. 167CPCh. 22 - Prob. 168CPCh. 22 - Prob. 169CPCh. 22 - Alcohols are very useful starting materials for...Ch. 22 - A chemical breathalyzer test works because ethanol...Ch. 22 - Estradiol is a female hormone with the following...Ch. 22 - Prob. 173IPCh. 22 - Prob. 174IPCh. 22 - Prob. 175MPCh. 22 - Prob. 176MP
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