Concept explainers
Assign each of the compounds in Problem 13-108 an IUPAC name in which the substituents on the benzene ring are located using the ortho-, meta-, para-prefix system.
(a)
Interpretation:
The IUPAC name has to be given for the disubstituted benzene derivative by using ortho-, meta-, para- prefix system.
Concept Introduction:
When hydrogen atoms are replaced by one or more groups in benzene is known as substitution reaction and the compounds produced is benzene derivatives.
Benzene derivative with one substituent:
IUPAC system of naming monosubstituted benzene derivatives uses the name of substituent as prefix to the name benzene. If the group that is present in benzene cannot be named easily means, then the benzene ring is often treated as group attached to this substituent. The benzene ring is known as phenyl in this approach.
Benzene derivative with two substituents:
When benzene ring contains two substituents it is known as disubstituted benzene derivative. Three isomers are possible for the disubstituted benzene derivative. The prefix used in IUPAC name are,
Ortho- means disubstitution in 1,2
Meta- means disubstitution in 1,3
Para- means disubstitution in 1,4
When both the substituents present on the benzene ring imparts a special name, where all the substituents are cited in alphabetical order before the ending –benzene. The carbon that bears the group with alphabetical priority is given number 1.
Benzene derivatives with three or more substituents:
More than two groups are present in the benzene ring means, their positions are numbered. The numbering is always done in a way that the carbon atom bearing substituent gets the lowest numbering possible. If there is a choice of numbering system, then the group that comes alphabetically first is given the lowest number.
Answer to Problem 2.110EP
The IUPAC name of the given compound is p-bromofluorobenzene.
Explanation of Solution
Given structure is,
From the structure given above, it is found a fluorine atom and a bromine atom are present as substituent. The numbering has to be given so that the substituents get the least numbering. The numbering has to be given considering the alphabetical order of the substituents. This puts the bromine in number 1 and fluorine in number 4. As the substituents are present in first and fourth position, prefix para- can be used to name the compound. Therefore, the IUPAC name can be given as p-bromofluorobenzene.
The IUPAC name can be given as p-bromofluorobenzene.
The correct IUPAC name for the given compound is given.
(b)
Interpretation:
The IUPAC name has to be given for the disubstituted benzene derivative by using ortho-, meta-, para- prefix system.
Concept Introduction:
When hydrogen atoms are replaced by one or more groups in benzene is known as substitution reaction and the compounds produced is benzene derivatives.
Benzene derivative with one substituent:
IUPAC system of naming monosubstituted benzene derivatives uses the name of substituent as prefix to the name benzene. If the group that is present in benzene cannot be named easily means, then the benzene ring is often treated as group attached to this substituent. The benzene ring is known as phenyl in this approach.
Benzene derivative with two substituents:
When benzene ring contains two substituents it is known as disubstituted benzene derivative. Three isomers are possible for the disubstituted benzene derivative. The prefix used in IUPAC name are,
Ortho- means disubstitution in 1,2
Meta- means disubstitution in 1,3
Para- means disubstitution in 1,4
When both the substituents present on the benzene ring imparts a special name, where all the substituents are cited in alphabetical order before the ending –benzene. The carbon that bears the group with alphabetical priority is given number 1.
Benzene derivatives with three or more substituents:
More than two groups are present in the benzene ring means, their positions are numbered. The numbering is always done in a way that the carbon atom bearing substituent gets the lowest numbering possible. If there is a choice of numbering system, then the group that comes alphabetically first is given the lowest number.
Answer to Problem 2.110EP
The IUPAC name of the given compound is m-ethylpropylbenzene.
Explanation of Solution
Given structure is,
From the structure given above, it is found an ethyl group and a propyl group is present as substituents. The numbering has to be given so that the substituents get the least numbering. The numbering has to be given considering the alphabetical order of the substituents. This puts the ethyl in number 1 and propyl in number 3. As the susbtituents are present in first and third carbon atom, meta- can be used in the name as prefix. Therefore, the IUPAC name can be given as m-ethylpropylbenzene.
The IUPAC name can be given as m-ethylpropylbenzene.
The correct IUPAC name for the given compound is given.
(c)
Interpretation:
The IUPAC name has to be given for the disubstituted benzene derivative by using ortho-, meta-, para- prefix system.
Concept Introduction:
When hydrogen atoms are replaced by one or more groups in benzene is known as substitution reaction and the compounds produced is benzene derivatives.
Benzene derivative with one substituent:
IUPAC system of naming monosubstituted benzene derivatives uses the name of substituent as prefix to the name benzene. If the group that is present in benzene cannot be named easily means, then the benzene ring is often treated as group attached to this substituent. The benzene ring is known as phenyl in this approach.
Benzene derivative with two substituents:
When benzene ring contains two substituents it is known as disubstituted benzene derivative. Three isomers are possible for the disubstituted benzene derivative. The prefix used in IUPAC name are,
Ortho- means disubstitution in 1,2
Meta- means disubstitution in 1,3
Para- means disubstitution in 1,4
When both the substituents present on the benzene ring imparts a special name, where all the substituents are cited in alphabetical order before the ending –benzene. The carbon that bears the group with alphabetical priority is given number 1.
Benzene derivatives with three or more substituents:
More than two groups are present in the benzene ring means, their positions are numbered. The numbering is always done in a way that the carbon atom bearing substituent gets the lowest numbering possible. If there is a choice of numbering system, then the group that comes alphabetically first is given the lowest number.
Answer to Problem 2.110EP
The IUPAC name of the given compound is o-diethylbenzene.
Explanation of Solution
Given structure is,
From the structure given above, it is found two ethyl groups are present as substituent. The numbering has to be given so that the substituents get the least numbering. This puts one ethyl group in position 1 and another ethyl group in position 2. As the groups substituted are identical, alphabetical order does not play a part but prefix di- has to be added. The groups that are substituted is present in first and second carbon atom. Hence, prefix ortho- can be used to name the compound. Therefore, the IUPAC name can be given as o-diethylbenzene.
The IUPAC name can be given as o-diethylbenzene.
The correct IUPAC name for the given compound is given.
(d)
Interpretation:
The IUPAC name has to be given for the disubstituted benzene derivative by using ortho-, meta-, para- prefix system.
Concept Introduction:
When hydrogen atoms are replaced by one or more groups in benzene is known as substitution reaction and the compounds produced is benzene derivatives.
Benzene derivative with one substituent:
IUPAC system of naming monosubstituted benzene derivatives uses the name of substituent as prefix to the name benzene. If the group that is present in benzene cannot be named easily means, then the benzene ring is often treated as group attached to this substituent. The benzene ring is known as phenyl in this approach.
Benzene derivative with two substituents:
When benzene ring contains two substituents it is known as disubstituted benzene derivative. Three isomers are possible for the disubstituted benzene derivative. The prefix used in IUPAC name are,
Ortho- means disubstitution in 1,2
Meta- means disubstitution in 1,3
Para- means disubstitution in 1,4
When both the substituents present on the benzene ring imparts a special name, where all the substituents are cited in alphabetical order before the ending –benzene. The carbon that bears the group with alphabetical priority is given number 1.
Benzene derivatives with three or more substituents:
More than two groups are present in the benzene ring means, their positions are numbered. The numbering is always done in a way that the carbon atom bearing substituent gets the lowest numbering possible. If there is a choice of numbering system, then the group that comes alphabetically first is given the lowest number.
Answer to Problem 2.110EP
The IUPAC name of the given compound is o-dimethylbenzene.
Explanation of Solution
Given structure is,
From the structure given above, it is found two methyl groups are present as substituent. The numbering has to be given so that the substituents get the least numbering. This puts one methyl group in position 1 and another methyl group in position 2. As the groups substituted are identical, alphabetical order does not play a part but prefix di- has to be added. The groups that are substituted is present in first and second carbon atom. Hence, prefix ortho- can be used to name the compound. Therefore, the IUPAC name can be given as o-dimethylbenzene.
The IUPAC name can be given as o-dimethylbenzene.
The correct IUPAC name for the given compound is given.
Want to see more full solutions like this?
Chapter 2 Solutions
Organic And Biological Chemistry
- c. Serricornin, the female-produced sex pheromone of the cigarette beetle, has the following structure. OH What is the maximum number of possible stereoisomers? Is this structure a meso compound? d. Please consider the natural product alkaloids shown below. Are these two structures enantiomers, diastereomers or conformers? H HO H H HN HO HN R R с R=H cinchonidine R=ET cinchonine Harrow_forwardNail polish remover containing acetone was spilled in a room 5.23 m × 3.28 m × 2.76 m. Measurements indicated that 2,250 mg of acetone evaporated. Calculate the acetone concentration in micrograms per cubic meter.arrow_forwardPlease help me answer number 1. 1. If your graphs revealed a mathematical relationship between specific heat and atomic mass, write down an equation for the relationship. I also don't understand, is the equation from the line regression the one that I'm suppose use to show the relationship? If so could you work it all the way out?arrow_forward
- Describe the principle of resonance and give a set of Lewis Structures to illustrate your explanation.arrow_forwardDon't used hand raitingarrow_forwardIt is not unexpected that the methoxyl substituent on a cyclohexane ring prefers to adopt the equatorial conformation. OMe H A G₂ = +0.6 kcal/mol OMe What is unexpected is that the closely related 2-methoxytetrahydropyran prefers the axial conformation: H H OMe OMe A Gp=-0.6 kcal/mol Methoxy: CH3O group Please be specific and clearly write the reason why this is observed. This effect that provides stabilization of the axial OCH 3 group in this molecule is called the anomeric effect. [Recall in the way of example, the staggered conformer of ethane is more stable than eclipsed owing to bonding MO interacting with anti-bonding MO...]arrow_forward
- 206 Pb 82 Express your answers as integers. Enter your answers separated by a comma. ▸ View Available Hint(s) VAΣ ΜΕ ΑΣΦ Np, N₁ = 82,126 Submit Previous Answers ? protons, neutronsarrow_forwardPlease draw the inverted chair forms of the products for the two equilibrium reactions shown below. Circle the equilibrium reaction that would have a AG = 0, i.e., the relative energy of the reactant (to the left of the equilibrium arrows) equals the relative energy of the product? [No requirement to show or do calculations.] CH3 CH3 HH CH3 1 -CH3arrow_forward5. Please consider the Newman projection of tartaric acid drawn below as an eclipsed conformer (1). Please draw the most stable conformer and two intermediate energy conformers noting that staggered conformers are lower in energy than eclipsed forms even if the staggered conformers have gauche relationships between groups. [Draw the substituents H and OH on the front carbons and H, OH and CO₂H on the back carbons based on staggered forms. -CO₂H is larger than -OH.] OH COH ICOOH COOH COOH 1 2 COOH COOH 3 4 Staggered Staggered Staggered (most stable) Indicate the number of each conformer above (1, 2, 3 and 4) that corresponds to the relative energies below. Ref=0 Rotation 6. (60 points) a. Are compounds 1 and 2 below enantiomers, diastereomers or identical? OH OH HO HO LOH HO HO OH 2 OH OH b. Please complete the zig-zag conformation of the compound (3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes. 3.arrow_forward
- The plutonium isotope with 144 neutrons Enter the chemical symbol of the isotope.arrow_forwardThe mass ratio of sodium to fluorine in sodium fluoride is 1.21:1. A sample of sodium fluoride produced 26.1 gg of sodium upon decomposition. How much fluorine was formed?arrow_forward32S 16 Enter your answers numerically separated by a comma. Np. Nn = 跖 ΟΙ ΑΣΦ Submit Request Answer ? protons, neutronsarrow_forward
- Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage LearningIntroduction 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 LearningWorld of Chemistry, 3rd editionChemistryISBN:9781133109655Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCostePublisher:Brooks / Cole / Cengage Learning