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(a)
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.
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 3.19EP
The structural formula is,
The correct IUPAC name of the given alcohol is 2-methyl-1-butanol.
Explanation of Solution
Given name of alcohol is 2-ethyl-1-propanol.
From the name it is identified that the parent alkane is propane with a hydroxyl group on first carbon atom and an ethyl group on second 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 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 substituent, a methyl group is present on the second carbon atom. This gives the IUPAC name of the alcohol as 2-methyl-1-butanol as hydroxyl is in the first carbon atom.
The structural formula for the given alcohol is drawn and correct IUPAC name is assigned.
(b)
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.
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 3.19EP
The structural formula is,
The correct IUPAC name of the given alcohol is 1,3-butanediol.
Explanation of Solution
Given name of alcohol is 2,4-butanediol.
From the name it is identified that there are two hydroxyl groups present each on second and fourth carbon atom of the parent alkane, butane. The structure can be drawn as,
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 four carbon chain and hence the parent is butane. As the structure has two hydroxyl groups in it, the suffix “-
The structural formula for the given alcohol is drawn and correct IUPAC name is assigned.
(c)
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.
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 3.19EP
The structural formula is,
The correct IUPAC name of the given alcohol is 3-methyl-2-butanol.
Explanation of Solution
Given name of alcohol is 2-methyl-3-butanol.
From the name it is identified that the parent alkane is butane with a methyl group substituted in second carbon atom and a hydroxyl
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 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 third carbon atom. This gives the IUPAC name of the alcohol as 3-methyl-2-butanol as hydroxyl is in the second carbon atom.
The structural formula for the given alcohol is drawn and correct IUPAC name is assigned.
(d)
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.
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 3.19EP
The structural formula is,
The correct IUPAC name of the given alcohol is 1,3-cyclopentanediol.
Explanation of Solution
Given name of alcohol is 1,4-cyclopentanediol.
From the name it is identified that the parent cycloalkane is cyclopentane with two hydroxyl groups at first and fourth carbon atom. The structure can be drawn as,
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 cyclic chain and hence the parent is cyclopentane. As the structure has two hydroxyl groups in it, the suffix “-diol” has to be added. 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 1,3-cyclopentanediol as hydroxyl groups are in the first and third carbon atom.
The structural formula for the given alcohol is drawn and correct IUPAC name is assigned.
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Chapter 3 Solutions
EBK ORGANIC AND BIOLOGICAL CHEMISTRY
- 3:48 PM Fri Apr 4 K Problem 4 of 10 Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Mg. :0: Select to Add Arrows :0: :Br: Mg :0: :0: Select to Add Arrows Mg. Br: :0: 0:0- Br -190 H 0:0 Select to Add Arrows Select to Add Arrows neutralizing workup H CH3arrow_forwardIarrow_forwardDraw the Markovnikov product of the hydrobromination of this alkene. Note for advanced students: draw only one product, and don't worry about showing any stereochemistry. Drawing dash and wedge bonds has been disabled for this problem. + Explanation Check 1 X E 4 1 1 1 1 1 HBr Click and drag to start drawing a structure. 80 LE #3 @ 2 $4 0 I அ2 % 85 F * K M ? BH 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center & 6 27 FG F10 8 9 R T Y U D F G H P J K L Z X C V B N M Q W A S H option command H command optiarrow_forward
- Be sure to use wedge and dash bonds to show the stereochemistry of the products when it's important, for example to distinguish between two different major products. Predict the major products of the following reaction. Explanation Q F1 A Check F2 @ 2 # 3 + X 80 F3 W E S D $ 4 I O H. H₂ 2 R Pt % 05 LL ee F6 F5 T <6 G Click and drag to start drawing a structure. 27 & A 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center Acce Y U H DII 8 9 F10 4 J K L Z X C V B N M T H option command F11 P H commandarrow_forwardCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the arrows to draw the intermediate and product in this reaction or mechanistic step(s). Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore inorganic byproducts. H :0: CH3 O: OH Q CH3OH2+ Draw Intermediate protonation CH3OH CH3OH nucleophilic addition H Draw Intermediate deprotonation :0: H3C CH3OH2* protonation H 0: H CH3 H.arrow_forwardPredicting the reactants or products of hemiacetal and acetal formation uentify the missing organic reactants in the following reaction: H+ X+Y OH H+ за Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H2O) are not shown. In the drawing area below, draw the skeletal ("line") structures of the missing organic reactants X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Explanation Check Click and drag to start drawing a structure. ? olo 18 Ar © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibilityarrow_forward
- can someone please answer thisarrow_forwardPlease, please help me figure out the the moles, molarity and Ksp column. Step by step details because I've came up with about three different number and have no idea what I'm doing wrong.arrow_forwardwhat reagents are used to get this product from this reactant? Br OCH3arrow_forward
- can someone answer this pleasearrow_forwardcan someone do the reaction mechanism for this reaction and draw the molecules for Q2 and q3arrow_forwardIn this question, the product of the aldol condensation is shown. What would be the reactants for this product? Please provide a detailed explanation, as well as a drawing showing how the reactants will react to produce the product.arrow_forward
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