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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Section
BuyFindarrow_forward

Organic And Biological Chemistry

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

Assign an IUPAC name to each of the alcohols in Problem 14-26.

Chapter 3, Problem 3.28EP, Assign an IUPAC name to each of the alcohols in Problem 14-26. , example  1

Chapter 3, Problem 3.28EP, Assign an IUPAC name to each of the alcohols in Problem 14-26. , example  2

Chapter 3, Problem 3.28EP, Assign an IUPAC name to each of the alcohols in Problem 14-26. , example  3

Chapter 3, Problem 3.28EP, Assign an IUPAC name to each of the alcohols in Problem 14-26. , example  4

(a)

Interpretation Introduction

Interpretation:

The IUPAC name for the alcohol has to be assigned.

Concept Introduction:

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”.  If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
  • • 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.
  • • If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
  • • In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer.  If the substitutions are present above and below the ring, then it is a trans isomer.

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 structure of alcohol is,

The longest carbon chain in the above structure with the hydroxyl group is found to be a five carbon chain.  Hence, the parent alkane is pentane.  As there is a double bond present in the carbon chain, the name is converted as pentene.  The hydroxyl group is found to be present on first carbon atom.  Therefore, the name of the given alcohol can be given as 2-penten-1-ol...

(b)

Interpretation Introduction

Interpretation:

The IUPAC name for the alcohol has to be assigned.

Concept Introduction:

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”.  If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
  • • 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.
  • • If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
  • • In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer.  If the substitutions are present above and below the ring, then it is a trans isomer.

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:

The IUPAC name for the alcohol has to be assigned.

Concept Introduction:

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”.  If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
  • • 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.
  • • If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
  • • In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer.  If the substitutions are present above and below the ring, then it is a trans isomer.

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:

The IUPAC name for the alcohol has to be assigned.

Concept Introduction:

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”.  If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
  • • 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.
  • • If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
  • • In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer.  If the substitutions are present above and below the ring, then it is a trans isomer.

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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