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Chapter 10: Problem 29

Draw structural formulas for each of these molecules and determine the number and type of bonds (single, double, or triple) for each carbon atom. a. \(\mathrm{H}_{3} \mathrm{CCN}\) (acetonitrile, used to make a type of plastic) b. \(\mathrm{H}_{2} \mathrm{NC}(\mathrm{O}) \mathrm{NH}_{2}\) (urea, an important fertilizer) c. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) (benzoic acid, a food preservative)

Short Answer

Expert verified
Acetonitrile: \(\mathrm{C-C\equivN}\) with single and triple bonds; Urea: \(\mathrm{NH_2-C=O-NH_2}\); Benzoic acid: benzene ring \(\mathrm{C_6H_5}\) and \(\mathrm{-COOH}\) group, involving single and double bonds.

Step by step solution

01

Draw the structure of Acetonitrile 0(60\(\mathrm{H}_{3} \mathrm{CCN}\)

Acetonitrile consists of a methyl group (\(\mathrm{CH_3}\)) attached to a nitrile group (\(\mathrm{CN}\)). Begin by drawing a \(\mathrm{CH_3}\) group, which has three single bonds connecting hydrogen atoms to a central carbon. This central carbon is then linked by a single bond to another carbon atom, which is triple-bonded to a nitrogen atom (\(\mathrm{-C\equivN}\)). Therefore, acetonitrile can be represented as \(\mathrm{H_3C-\equivN}\).
02

Identify Bonds for Acetonitrile

In the structure of acetonitrile, the first carbon atom (in \(\mathrm{CH_3}\)) is bonded with three single bonds to hydrogen atoms and one single bond to another carbon atom, making a total of four bonds. The second carbon atom forms a single bond with the first carbon atom and a triple bond with nitrogen.
03

Draw the structure of Urea 60(60\(\mathrm{H}_{2} 60\mathrm{NC(O)NH}_{2}\)

Urea consists of a central carbon atom that forms a double bond with an oxygen atom (forming a carbonyl group \((\mathrm{C=O})\)) and two \(\mathrm{NH}_2\) groups. Each \(\mathrm{NH}_2\) consists of nitrogen singly bonded to two hydrogens, connected to the central carbon. Thus, the urea structure is \(\mathrm{H_2N-CO-NH_2}\).
04

Identify Bonds for Urea

In the urea molecule, the central carbon atom is double-bonded to oxygen and single-bonded to two nitrogen atoms, as follows: \((\mathrm{-NH_2})\text{-} (\mathrm{C=O})\text{-}(\mathrm{NH_2})\). Each nitrogen atom is single-bonded to two hydrogen atoms.
05

Draw the structure of Benzoic Acid 60(60\(\mathrm{C}_{6} 60\mathrm{H}_{5} 60\mathrm{COOH}\)

The benzoic acid molecule consists of a benzene ring \( (\mathrm{C_6H_5}) \) with an attached carboxyl group \((\mathrm{-COOH})\). The benzene ring is represented by a hexagon with alternating double bonds between carbon atoms and each carbon atom in the ring carries one hydrogen atom except the one bonded to the carboxyl group. The carboxyl group implicates a carbon atom double-bonded to an oxygen and single-bonded to a hydroxyl group \((\mathrm{-OH})\).
06

Identify Bonds for Benzoic Acid

In benzoic acid, each carbon in the benzene ring is involved in alternating single and double bonds. The carboxyl group consists of one single-bonded (hydroxyl) and one double-bonded oxygen, with the carbon in the group linked by a single bond to the benzene ring.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Acetonitrile
Acetonitrile is a simple organic compound that serves as a building block for various applications, including the production of plastics. It is represented by the chemical formula \( \mathrm{H_3CCN} \). In the structural formula of acetonitrile, a methyl group (\( \mathrm{CH_3} \)) is attached to a nitrile group (\( \mathrm{CN} \)).
The methyl group consists of three single bonds connecting hydrogen atoms to a central carbon. This carbon atom is then linked to another carbon atom by a single bond.
  • The second carbon atom forms a triple bond with a nitrogen atom in the nitrile group. This gives acetonitrile its characteristic linear structure, represented as \( \mathrm{H_3C-}\equiv\mathrm{N} \).
In summary, the molecule contains:
  • Four bonds for the first carbon atom (three single to hydrogen and one single to another carbon).
  • A single bond between the two carbon atoms.
  • A triple bond between the second carbon and the nitrogen atom.
Urea
Urea is a vital compound predominantly used as a nitrogen-release fertilizer. It is characterized by the chemical formula \( \mathrm{H_2NC(O)NH_2} \), featuring a central carbon atom that forms a double bond with an oxygen atom, known as a carbonyl group.
Two amine groups (\( \mathrm{NH_2} \)) are also connected to this central carbon.
In the structural formula of urea:
  • The carbonyl group is formed by a double bond with oxygen, creating a key functional group for the molecule.
  • Each amine group consists of one nitrogen atom single-bonded to two hydrogen atoms and connects to the central carbon with a single bond. This arrangement is denoted as \( \mathrm{H_2N-CO-NH_2} \).
The carbon atom in urea thus has:
  • Two single bonds with nitrogen atoms from the amine groups.
  • One double bond with oxygen.
Benzoic Acid
Benzoic acid is an aromatic compound commonly used as a food preservative. Its chemical formula is \( \mathrm{C_6H_5COOH} \). The structure includes a benzene ring and a carboxyl group (\( \mathrm{-COOH} \)).
In the benzoic acid molecule:
  • The benzene ring is depicted as a hexagon with alternating double bonds between carbon atoms. Each carbon in the ring is bonded to one hydrogen atom. This gives it stable aromatic properties.
  • Connected to the benzene ring by a single bond is the carboxyl group. This group features a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group (\( \mathrm{-OH} \)).
Elements within benzoic acid include:
  • Single and double bonds within the benzene ring.
  • Single bond linking the carboxyl group to the benzene ring.
  • Double and single bonds within the carboxyl group.
Chemical Bonding
Chemical bonding is the process of atoms joining together to form molecules, enabling the existence of complex substances such as acetonitrile, urea, and benzoic acid. Different types of bonds include single, double, and triple bonds, each with distinct characteristics.
  • **Single Bonds**: Involves two atoms sharing one pair of electrons. They are the simplest and most flexible type of bond, allowing free rotational movement.
  • **Double Bonds**: Form when two pairs of electrons are shared between atoms. They create shorter and stronger connections than single bonds and restrict rotational freedom.
  • **Triple Bonds**: Characterized by the sharing of three electron pairs. These are the strongest and shortest molecular bonds, providing greater stability.
Acetonitrile, urea, and benzoic acid each exhibit these varied bonding types, affecting their respective structures and functions.
Carbon Atom Bonds
Carbon atoms can form diverse structures due to their ability to create stable bonds with other carbon atoms and various elements. This versatility is crucial, especially in organic chemistry.
  • A carbon atom can establish up to four bonds, allowing for a wide variety of bonding scenarios.
  • Single, double, and triple bonds change the geometry and stability of carbon-containing molecules.
For example, acetonitrile showcases:
  • One carbon bonded to three hydrogens and another carbon, then linked to nitrogen through a triple bond.
In urea, the central carbon forms:
  • Two single bonds with nitrogen atoms and one double bond with oxygen.
And in benzoic acid, the interplay of single and double bonds forms the aromatic benzene ring and connects to the carboxyl functional group. Each configuration allows carbon compounds to play crucial roles in various chemical processes and applications.

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