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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Each of the following alcohols is named incorrectly. However, the names give correct structural formulas. Draw structural formulas for the compounds, and then write the correct IUPAC name for each alcohol.

  1. a. 3-Ethyl-2-butanol
  2. b. 3,4-Pentanediol
  3. c. 3-Methyl-3-butanol
  4. d. 1,1-Dimethyl-1-butanol

(a)

Interpretation Introduction

Interpretation:

Structural formula has to be written for the given alcohols and correct IUPAC name has to be assigned.

Concept Introduction:

The structural representation of organic compound can be done in 2D and 3D. In two-dimensional representation, there are four types of representation in which an organic compound can be drawn. They are,

  • Expanded structural formula
  • Condensed structural formula
  • Skeletal structural formula
  • Line-angle structural formula

Structural formula which shows all the atoms in a molecule along with all the bonds that is connecting the atoms present in the molecule is known as expanded structural formula.

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Structural formula that shows the bonding between carbon atoms alone in the molecule ignoring the hydrogen atoms being shown explicitly is known as Skeletal structural formula.

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula.

Organic And Biological Chemistry, Chapter 3, Problem 3.20EP , additional homework tip  1

IUPAC rules for naming alcohols that contain single hydroxyl group:

  • Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”.
  • The numbering has to be given so that the hydroxyl group gets the least numbering.
  • Name and location of any other substituent present in the chain has to be identified.
  • If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
  • Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

  • The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.
Explanation

Given name of alcohol is 3-ethyl-2-butanol.

From the name it is identified that the parent alkane is butane with a hydroxyl group on second carbon atom and an ethyl group on third carbon atom.

The structural formula for the given alcohol is drawn as shown above.

IUPAC name can be identified by finding the longest continuous carbon chain with the hydroxyl group. In this case it is found to be a five carbon chain and hence the parent is pentane...

(b)

Interpretation Introduction

Interpretation:

Structural formula has to be written for the given alcohols and correct IUPAC name has to be assigned.

Concept Introduction:

The structural representation of organic compound can be done in 2D and 3D. In two-dimensional representation, there are four types of representation in which an organic compound can be drawn. They are,

  • Expanded structural formula
  • Condensed structural formula
  • Skeletal structural formula
  • Line-angle structural formula

Structural formula which shows all the atoms in a molecule along with all the bonds that is connecting the atoms present in the molecule is known as Expanded structural formula.

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Structural formula that shows the bonding between carbon atoms alone in the molecule ignoring the hydrogen atoms being shown explicitly is known as Skeletal structural formula.

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula.

Organic And Biological Chemistry, Chapter 3, Problem 3.20EP , additional homework tip  2

IUPAC rules for naming alcohols that contain single hydroxyl group:

  • Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”.
  • The numbering has to be given so that the hydroxyl group gets the least numbering.
  • Name and location of any other substituent present in the chain has to be identified.
  • If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
  • Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

  • The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

(c)

Interpretation Introduction

Interpretation:

Structural formula has to be written for the given alcohols and correct IUPAC name has to be assigned.

Concept Introduction:

The structural representation of organic compound can be done in 2D and 3D. In two-dimensional representation, there are four types of representation in which an organic compound can be drawn. They are,

  • Expanded structural formula
  • Condensed structural formula
  • Skeletal structural formula
  • Line-angle structural formula

Structural formula which shows all the atoms in a molecule along with all the bonds that is connecting the atoms present in the molecule is known as Expanded structural formula.

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Structural formula that shows the bonding between carbon atoms alone in the molecule ignoring the hydrogen atoms being shown explicitly is known as Skeletal structural formula.

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula.

Organic And Biological Chemistry, Chapter 3, Problem 3.20EP , additional homework tip  3

IUPAC rules for naming alcohols that contain single hydroxyl group:

  • Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”.
  • The numbering has to be given so that the hydroxyl group gets the least numbering.
  • Name and location of any other substituent present in the chain has to be identified.
  • If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
  • Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

  • The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

(d)

Interpretation Introduction

Interpretation:

Structural formula has to be written for the given alcohols and correct IUPAC name has to be assigned.

Concept Introduction:

The structural representation of organic compound can be done in 2D and 3D. In two-dimensional representation, there are four types of representation in which an organic compound can be drawn. They are,

  • Expanded structural formula
  • Condensed structural formula
  • Skeletal structural formula
  • Line-angle structural formula

Structural formula which shows all the atoms in a molecule along with all the bonds that is connecting the atoms present in the molecule is known as Expanded structural formula.

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Structural formula that shows the bonding between carbon atoms alone in the molecule ignoring the hydrogen atoms being shown explicitly is known as Skeletal structural formula.

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula.

Organic And Biological Chemistry, Chapter 3, Problem 3.20EP , additional homework tip  4

IUPAC rules for naming alcohols that contain single hydroxyl group:

  • Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”.
  • The numbering has to be given so that the hydroxyl group gets the least numbering.
  • Name and location of any other substituent present in the chain has to be identified.
  • If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
  • Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

  • The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

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