Study Guide/solutions Manual For Organic Chemistry
Study Guide/solutions Manual For Organic Chemistry
6th Edition
ISBN: 9781260475678
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 1, Problem 40P

Citric acid is responsible for the tartness of citrus fruits, especially lemons and limes.

Chapter 1, Problem 40P, Citric acid is responsible for the tartness of citrus fruits, especially lemons and limes. a.What is

a. What is the molecular formula of citric acid?

b. How many lone pairs are present?

c. Draw a skeletal structure.

d. How many s p 2 hybridized carbon atoms are present?

e. What orbitals are used to form each indicated bond ( [ 1 ] [ 4 ] ) ?

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The molecular formula of citric acid is to be stated.

Concept introduction: In ball-and-stick model, each colored ball represents a specific atom and each stick represents a bond. In this model, each black ball represents C atoms, each gray ball represents H atoms, and each red ball represents O atoms.

Answer to Problem 40P

The molecular formula of citric acid is C6H8O7.

Explanation of Solution

The given ball-and-stick model of citric acid is,

Study Guide/solutions Manual For Organic Chemistry, Chapter 1, Problem 40P , additional homework tip  1

Figure 1

In ball-and-stick model, each colored ball represents a specific atom and each stick represents a bond. In this model, each black ball represents C atoms, each gray ball represents H atoms, and each red ball represents O atoms.

In the above model,

• There are seven red balls. Thus, there are seven O atoms.

• There are six black balls. Thus, there are six C atoms.

• There are eight grey balls. Thus, there are eight H atoms.

Hence, the molecular formula of citric acid is C6H8O7.

Conclusion

The molecular formula of citric acid is C6H8O7.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The number of lone pairs present in citric acid is to be stated.

Concept introduction: In a compound or molecule, the lone pairs represent number of unshared electrons on atom. An atom may or may not have unshared electrons. For example, carbon and hydrogen atoms have no lone pair but each oxygen atom has two lone pairs.

Answer to Problem 40P

There are total 14 lone pairs in citric acid.

Explanation of Solution

The molecular formula of citric acid is C6H8O7. Carbon and hydrogen atoms have no lone pair, but each oxygen atom has two lone pairs. There are seven oxygen atoms in citric acid. Thus, there are total 14 lone pairs (7×2=14) in citric acid.

Conclusion

There are total 14 lone pairs in citric acid.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: A skeletal structure of citric acid is to be drawn.

Concept introduction: A ball-and-stick model is converted into skeletal structure by replacing black ball with C, gray ball with H, and red ball with O. Omit the H atom on carbon, but not in the case of heteroatom.

Answer to Problem 40P

A skeletal structure of citric acid is,

Study Guide/solutions Manual For Organic Chemistry, Chapter 1, Problem 40P , additional homework tip  2

Explanation of Solution

In ball-and-stick model each colored ball represents a specific atom and each stick represents a bond. A ball-and-stick model is converted into skeletal structure by replacing black ball with C, gray ball with H, red ball with O, and blue ball with N. Omit the H atom on carbon, but not in the case of heteroatom.

A skeletal structure of citric acid is shown in Figure 2.

Study Guide/solutions Manual For Organic Chemistry, Chapter 1, Problem 40P , additional homework tip  3

Figure 2

Conclusion

In ball-and-stick model each colored ball represents a specific atom and each stick represents a bond.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The number of sp2 hybridized carbon in citric acid is to be stated.

Concept introduction: According to the rule of hybridization, an atom that is surrounded with two groups is sp hybridized, an atom that is surrounded with three groups is sp2 hybridized, and an atom that is surrounded with four groups is sp3 hybridized.

Answer to Problem 40P

There are three sp2 hybridized carbon atoms in citric acid.

Study Guide/solutions Manual For Organic Chemistry, Chapter 1, Problem 40P , additional homework tip  4

Explanation of Solution

The Lewis structure of citric acid is,

Study Guide/solutions Manual For Organic Chemistry, Chapter 1, Problem 40P , additional homework tip  5

Figure 3

According to the rules of hybridization, an atom that is surrounded with two groups is sp hybridized, an atom that is surrounded with three groups is sp2 hybridized, and an atom that is surrounded with four groups is sp3 hybridized.

The sp2 hybridized carbon atoms (surrounded by three groups) are shown in Figure 4.

Study Guide/solutions Manual For Organic Chemistry, Chapter 1, Problem 40P , additional homework tip  6

Figure 4

Thus, there are three sp2 hybridized carbon atoms in citric acid.

Conclusion

There are three sp2 hybridized carbon atoms in citric acid.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The orbitals that are used to form each indicated bond is to be stated.

Concept introduction: According to the rule of hybridization, an atom that is surrounded with two groups is sp hybridized, an atom that is surrounded with three groups is sp2 hybridized, and an atom that is surrounded with four groups is sp3 hybridized.

Answer to Problem 40P

Bond [1] is formed by Csp2Osp2 hybridized orbitals. Bond [2] is formed by Csp2Csp3 hybridized orbitals. Bond [3] is formed by Osp3H1s orbitals. Bond [4] is formed by Csp3Osp3 hybridized orbitals.

Explanation of Solution

Bond [1] represents C=O bond, in which both carbon atom and oxygen atom are sp2 hybridized. Thus, it is formed by Csp2Osp2 hybridized orbitals.

Bond [2] represents bonding between the carbon atom of carbonyl group (C=O), and the carbon atom of CH2 group. The carbon atom of carbonyl group is sp2 hybridized and the carbon atom of CH2 group is sp3 hybridized.

Thus, [2] is formed by Csp2Csp3 hybridized orbitals.

Bond [3] represents, OH bond. This bond is formed through sp3 hybridized orbital of oxygen and 1s orbital of hydrogen.

Thus, [3] is formed by Osp3H1s orbitals.

Bond [4] represents, CO bond, in which both carbon atom and oxygen atom are sp3 hybridized. Thus, [4] is formed by Csp3Osp3 hybridized orbitals.

Conclusion

The number of surrounded group around any atom predicts the hybridization of that atom, which is further helpful to predict the orbitals involve in bond formation.

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Study Guide/solutions Manual For Organic Chemistry

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