Videos
(a)
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.
(a)
Answer to Problem 14.27EP
The IUPAC name of the given alcohol is trans-2-buten-1-ol.
Explanation of Solution
Given structure of alcohol is,
The longest carbon chain in the above structure with the hydroxyl group is found to be a four carbon chain. Hence, the parent alkane is butane. As there is a double bond present in the carbon chain, the name is converted as butene. The hydroxyl group is found to be present on first carbon atom. Therefore, the name of the given alcohol can be given as 2-buten-1-ol.
Looking for the stereochemistry, the given structure has bulky group on opposite side of the double bond and hence this is a trans isomer. This has to be included in the IUPAC name. Therefore, IUPAC name of the given compound is trans-2-buten-1-ol.
IUPAC name for the given alcohol is trans-2-buten-1-ol.
(b)
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.
(b)
Answer to Problem 14.27EP
The IUPAC name of the given alcohol is cis-3-penten-1-ol.
Explanation of Solution
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 and the double bond between third and fourth carbon atom. Therefore, the name of the given alcohol can be given as 3-penten-1-ol.
Looking for the stereochemistry, the given structure has bulky group on same side of the double bond and hence this is a cis isomer. This has to be included in the IUPAC name. Therefore, IUPAC name of the given compound is cis-3-penten-1-ol.
IUPAC name for the given alcohol is cis-3-penten-1-ol.
(c)
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)
Answer to Problem 14.27EP
The IUPAC name of the given alcohol is cis-2-methylcyclohexanol.
Explanation of Solution
Given structure of alcohol is,
The longest carbon chain in the above structure with the hydroxyl group is found to be a six carbon cyclic chain. Hence, the parent cycloalkane is cyclohexane. As a hydroxyl group is present in the ring, the name can be given as cyclohexanol. Looking for the substituents present in the ring, it is found that a methyl group is present in the second position. Therefore, the name of the given alcohol can be given as 2-methylcyclohexanol.
Looking for the stereochemistry, the given structure has substituents on same side of the ring of carbon atoms and hence this is a cis isomer. This has to be included in the IUPAC name. Therefore, IUPAC name of the given compound is cis-2-methylcyclohexanol.
IUPAC name for the given alcohol is cis-2-methylcyclohexanol.
(d)
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)
Answer to Problem 14.27EP
The IUPAC name of the given alcohol is trans-3-chlorocyclohexanol.
Explanation of Solution
Given structure of alcohol is,
The longest carbon chain in the above structure with the hydroxyl group is found to be a six carbon cyclic chain. Hence, the parent cycloalkane is cyclohexane. As a hydroxyl group is present in the ring, the name can be given as cyclohexanol. Looking for the substituents present in the ring, it is found that a chloro is present in the third position. Therefore, the name of the given alcohol can be given as 3-chlorocyclohexanol.
Looking for the stereochemistry, the given structure has substituents above and below the ring of carbon atoms and hence this is a trans isomer. This has to be included in the IUPAC name. Therefore, IUPAC name of the given compound is trans-3-chlorocyclohexanol.
IUPAC name for the given alcohol is trans-3-chlorocyclohexanol.
Want to see more full solutions like this?
Chapter 14 Solutions
Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th
- Explanation O Conjugated Pi Systems Deducing the reactants of a Diels-Alder reaction Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. Click and drag to start drawing a structure. Xarrow_forwardDiels Alder Cycloaddition: Focus on regiochemistry (problems E-F) –> match + of thedienophile and - of the diene while also considering stereochemistry (endo).arrow_forwardHELP! URGENT! PLEASE RESOND ASAP!arrow_forward
- Question 4 Determine the rate order and rate constant for sucrose hydrolysis. Time (hours) [C6H12O6] 0 0.501 0.500 0.451 1.00 0.404 1.50 0.363 3.00 0.267 First-order, k = 0.210 hour 1 First-order, k = 0.0912 hour 1 O Second-order, k = 0.590 M1 hour 1 O Zero-order, k = 0.0770 M/hour O Zero-order, k = 0.4896 M/hour O Second-order, k = 1.93 M-1-hour 1 10 ptsarrow_forwardDetermine the rate order and rate constant for sucrose hydrolysis. Time (hours) [C6H12O6] 0 0.501 0.500 0.451 1.00 0.404 1.50 0.363 3.00 0.267arrow_forwardDraw the products of the reaction shown below. Use wedge and dash bonds to indicate stereochemistry. Ignore inorganic byproducts. OSO4 (cat) (CH3)3COOH Select to Draw ઘarrow_forward
- Calculate the reaction rate for selenious acid, H2SeO3, if 0.1150 M I-1 decreases to 0.0770 M in 12.0 minutes. H2SeO3(aq) + 6I-1(aq) + 4H+1(aq) ⟶ Se(s) + 2I3-1(aq) + 3H2O(l)arrow_forwardProblem 5-31 Which of the following objects are chiral? (a) A basketball (d) A golf club (b) A fork (c) A wine glass (e) A spiral staircase (f) A snowflake Problem 5-32 Which of the following compounds are chiral? Draw them, and label the chirality centers. (a) 2,4-Dimethylheptane (b) 5-Ethyl-3,3-dimethylheptane (c) cis-1,4-Dichlorocyclohexane Problem 5-33 Draw chiral molecules that meet the following descriptions: (a) A chloroalkane, C5H11Cl (c) An alkene, C6H12 (b) An alcohol, C6H140 (d) An alkane, C8H18 Problem 5-36 Erythronolide B is the biological precursor of erythromycin, a broad-spectrum antibiotic. How H3C CH3 many chirality centers does erythronolide B have? OH Identify them. H3C -CH3 OH Erythronolide B H3C. H3C. OH OH CH3arrow_forwardPLEASE HELP! URGENT! PLEASE RESPOND!arrow_forward
- 2. Propose a mechanism for this reaction. ہلی سے ملی N H (excess)arrow_forwardSteps and explanationn please.arrow_forwardProblem 5-48 Assign R or S configurations to the chirality centers in ascorbic acid (vitamin C). OH H OH HO CH2OH Ascorbic acid O H Problem 5-49 Assign R or S stereochemistry to the chirality centers in the following Newman projections: H Cl H CH3 H3C. OH H3C (a) H H H3C (b) CH3 H Problem 5-52 Draw the meso form of each of the following molecules, and indicate the plane of symmetry in each: OH OH (a) CH3CHCH2CH2CHCH3 CH3 H3C. -OH (c) H3C CH3 (b) Problem 5-66 Assign R or S configurations to the chiral centers in cephalexin, trade-named Keflex, the most widely prescribed antibiotic in the United States. H2N H IHH S Cephalexin N. CH3 CO₂Harrow_forward
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning