(a)
Interpretation:
Condensed structural formula has to be written for the given alcohols and 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.
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.
(a)
Answer to Problem 14.14EP
The condensed structural formula is,
The IUPAC name of the given alcohol is 1-butanol.
Explanation of Solution
Given name of alcohol is butyl alcohol.
From the name it is identified that the alkyl group is butyl and the hydroxyl group is attached to the first carbon atom. The structure can be drawn as,
The condensed 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 four carbon chain and hence the parent is butane. As the structure has a hydroxyl group in it, the suffix “-ol” has to be added instead of “-e” in the parent alkane. The numbering has to be given in a way that the hydroxyl group gets the least numbering. This gives the IUPAC name of the alcohol as 1-butanol as hydroxyl is in the first carbon atom.
The condensed structural formula for the given alcohol is drawn and IUPAC name is assigned.
(b)
Interpretation:
Condensed structural formula has to be written for the given alcohols and 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.
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.
(b)
Answer to Problem 14.14EP
The condensed structural formula is,
The IUPAC name of the given alcohol is 1-hexanol.
Explanation of Solution
Given name of alcohol is hexyl alcohol.
From the name it is identified that the alkyl group is hexyl and the hydroxyl group is attached to the first carbon atom. The structure can be drawn as,
The condensed 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 six carbon chain and hence the parent is hexane. As the structure has a hydroxyl group in it, the suffix “-ol” has to be added instead of “-e” in the parent alkane. The numbering has to be given in a way that the hydroxyl group gets the least numbering. This gives the IUPAC name of the alcohol as 1-hexanol as hydroxyl is in the first carbon atom.
The condensed structural formula for the given alcohol is drawn and IUPAC name is assigned.
(c)
Interpretation:
Condensed structural formula has to be written for the given alcohols and 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.
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)
Answer to Problem 14.14EP
The condensed structural formula is,
The IUPAC name of the given alcohol is 2-propanol.
Explanation of Solution
Given name of alcohol is isopropyl alcohol.
From the name it is identified that the alkyl group is isopropyl and the hydroxyl group is attached present. The structure can be drawn as,
The condensed 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 three carbon chain and hence the parent is propane. As the structure has a hydroxyl group in it, the suffix “-ol” has to be added instead of “-e” in the parent alkane. The numbering has to be given in a way that the hydroxyl group gets the least numbering. This gives the IUPAC name of the alcohol as 2-propanol as hydroxyl is in the second carbon atom.
The condensed structural formula for the given alcohol is drawn and IUPAC name is assigned.
(d)
Interpretation:
Condensed structural formula has to be written for the given alcohols and 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.
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)
Answer to Problem 14.14EP
The condensed structural formula is,
The IUPAC name of the given alcohol is 2-methyl-2-propanol.
Explanation of Solution
Given name of alcohol is tert-butyl alcohol.
From the name it is identified that the alkyl group is tert-butyl and the hydroxyl group is attached to the second carbon atom. The structure can be drawn as,
The condensed 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 four carbon chain and hence the parent is butane. As the structure has a hydroxyl group in it, the suffix “-ol” has to be added instead of “-e” in the parent alkane. The numbering has to be given in a way that the hydroxyl group gets the least numbering. Looking for the substituents, a methyl group is present in the second carbon atom. This gives the IUPAC name of the alcohol as 2-methyl-2-propanol as hydroxyl is in the second carbon atom.
The condensed structural formula for the given alcohol is drawn and IUPAC name is assigned.
Want to see more full solutions like this?
Chapter 14 Solutions
EBK GENERAL, ORGANIC, AND BIOLOGICAL CH
- Salol, the phenyl ester of salicylic acid, is used as an intestinal antiseptic. Draw the structure of phenyl salicylate.arrow_forwardSalicylic acid (o-hydroxybenzoic acid) is used as starting material to prepare aspirin. Draw the structure of salicylic acid.arrow_forwardFor the first part, draw a Fischer projection formula for the enantiomer of each of the following monosaccharides. For the second part, identify whether the images are in D- or L-configuration. Write your answers first on a piece of bond paper.arrow_forward
- The explosive trinitrotoluene (TNT) is made by carrying out three successive nitration reactions on toluene. If these nitrations only occur in the ortho and para positions relative to the methyl group, what is the structure of TNT?arrow_forwardThe following compound can be described as a(an)arrow_forwardIDENTIFY THE FUNCTIONAL GROUP PRESENT IN THESE COMPOUNDS. A = ? B = ? C = ?arrow_forward
- For A, B, C, D, E, F, identify the circled functional groups and linkages in the compound in the picture.arrow_forwardSpermaceti, a fragrant substance isolated from sperm whales, was commonly used in cosmetics until it was banned in 1976 to protect the whales from extinction. Chemically, spermaceti is cetyl palmitate, the ester of palmiticacid with cetyl alcohol (the straight-chain 16-carbon alcohol). Draw the structure of spermaceti.arrow_forwardDraw a Lewis structure for hydroxylamine, NH2OH.arrow_forward
- Fumaric acid is a metabolic intermediate that has the systematic name trans-2-butenedioic acid. Draw its structure.arrow_forwardWhen Alfred Werner was developing the field of coordination chemistry, it was argued by some that the optical activity he observed in the chiral complexes he had prepared was due to the presence of carbon atoms in themolecule. To disprove this argument, Werner synthesized a chiral complex of cobalt that had no carbon atoms in it, and he was able to resolve it into its enantiomers. Design a cobalt(III) complex that would be chiral if it could be synthesized and that contains no carbon atoms.arrow_forwardD- and L- designations are used to distinguish between the two possible enantiomers of the monosaccharide, galactose. From the Fischer projection, determine the designation of this monosaccharide.arrow_forward
- Human Anatomy & Physiology (11th Edition)BiologyISBN:9780134580999Author:Elaine N. Marieb, Katja N. HoehnPublisher:PEARSONBiology 2eBiologyISBN:9781947172517Author:Matthew Douglas, Jung Choi, Mary Ann ClarkPublisher:OpenStaxAnatomy & PhysiologyBiologyISBN:9781259398629Author:McKinley, Michael P., O'loughlin, Valerie Dean, Bidle, Theresa StouterPublisher:Mcgraw Hill Education,
- Molecular Biology of the Cell (Sixth Edition)BiologyISBN:9780815344322Author:Bruce Alberts, Alexander D. Johnson, Julian Lewis, David Morgan, Martin Raff, Keith Roberts, Peter WalterPublisher:W. W. Norton & CompanyLaboratory Manual For Human Anatomy & PhysiologyBiologyISBN:9781260159363Author:Martin, Terry R., Prentice-craver, CynthiaPublisher:McGraw-Hill Publishing Co.Inquiry Into Life (16th Edition)BiologyISBN:9781260231700Author:Sylvia S. Mader, Michael WindelspechtPublisher:McGraw Hill Education