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Concept explainers
(a)
Interpretation:
The complete IUPAC name of the given molecule is to be determined.
Concept introduction:
A ring compound with a double bond and eight or more carbon atoms can have both E and Z configurations at the double bond. Rings containing seven carbon atoms or less have only Z configuration. The E configuration is too unstable because of a high ring strain. The E/Z designation is generally left out in this case.
The E/Z configuration is determined on the basis of the priorities of the two groups attached to the double bonded carbon atoms. Priority is assigned on the basis of the atomic number of the atom directly bonded to the double bonded carbon. Higher the atomic number, higher the priority. If the
When writing the name, the E/Z designation is written at the start, in parenthesis. If there are two or more double bonds, then they are listed with the respective locants.
If the higher priority groups at the two ends are on the same side of the double bond, then the compound is assigned a Z configuration. If they are on the opposite sides of the double bond, then an E configuration is assigned.
For determining the R/S configuration, the groups attached to the asymmetric center are assigned priorities, following the same rules outlined above. If the groups with priorities 1 to 3 are arranged clockwise with the lowest priority group going away from the observer, the asymmetric center is assigned R configuration. If they are arranged counterclockwise, the configuration assigned is S.
When writing the IUPAC name of a molecule, each R and S designation can be written immediately before the first number used to locate the substituent attached to the asymmetric carbon atom. An alternate way is to write all the R and S designations together at the front of the name. The locator number for each asymmetric carbon atom must appear before its R or S designation, and the designations must be separated from each other by a comma.
(b)
Interpretation:
The complete IUPAC name of the given molecule is to be determined.
Concept introduction:
A ring compound with a double bond and eight or more carbon atoms can have both E and Z configurations at the double bond. Rings containing seven carbon atoms or less have only Z configuration. The E configuration is too unstable because of a high ring strain. The E/Z designation is generally left out in this case.
The E/Z configuration is determined on the basis of the priorities of the two groups attached to the double bonded carbon atoms. Priority is assigned on the basis of the atomic number of the atom directly bonded to the double bonded carbon. Higher the atomic number, higher the priority. If the atomic numbers of both atoms attached to a carbon are the same, then the priority is determined on the basis of the atoms one bond away from the point of attachment.
When writing the name, the E/Z designation is written at the start, in parenthesis. If there are two or more double bonds, then they are listed with the respective locants.
If the higher priority groups at the two ends are on the same side of the double bond, then the compound is assigned a Z configuration. If they are on the opposite sides of the double bond, then an E configuration is assigned.
For determining the R/S configuration, the groups attached to the asymmetric center are assigned priorities, following the same rules outlined above. If the groups with priorities 1 to 3 are arranged clockwise with the lowest priority group going away from the observer, the asymmetric center is assigned R configuration. If they are arranged counterclockwise, the configuration assigned is S.
When writing the IUPAC name of a molecule, each R and S designation can be written immediately before the first number used to locate the substituent attached to the asymmetric carbon atom. An alternate way is to write all the R and S designations together at the front of the name. The locator number for each asymmetric carbon atom must appear before its R or S designation, and the designations must be separated from each other by a comma.
(c)
Interpretation:
The complete IUPAC name of the given molecule is to be determined.
Concept introduction:
A ring compound with a double bond and eight or more carbon atoms can have both E and Z configurations at the double bond. Rings containing seven carbon atoms or less have only Z configuration. The E configuration is too unstable because of a high ring strain. The E/Z designation is generally left out in this case.
The E/Z configuration is determined on the basis of the priorities of the two groups attached to the double bonded carbon atoms. Priority is assigned on the basis of the atomic number of the atom directly bonded to the double bonded carbon. Higher the atomic number, higher the priority. If the atomic numbers of both atoms attached to a carbon are the same, then the priority is determined on the basis of the atoms one bond away from the point of attachment.
When writing the name, the E/Z designation is written at the start, in parenthesis. If there are two or more double bonds, then they are listed with the respective locants.
If the higher priority groups at the two ends are on the same side of the double bond, then the compound is assigned a Z configuration. If they are on the opposite sides of the double bond, then an E configuration is assigned.
For determining the R/S configuration, the groups attached to the asymmetric center are assigned priorities, following the same rules outlined above. If the groups with priorities 1 to 3 are arranged clockwise with the lowest priority group going away from the observer, the asymmetric center is assigned R configuration. If they are arranged counterclockwise, the configuration assigned is S.
When writing the IUPAC name of a molecule, each R and S designation can be written immediately before the first number used to locate the substituent attached to the asymmetric carbon atom. An alternate way is to write all the R and S designations together at the front of the name. The locator number for each asymmetric carbon atom must appear before its R or S designation, and the designations must be separated from each other by a comma.
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Chapter C Solutions
Organic Chemistry: Principles And Mechanisms
- Acid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 HO- H₂O 2. Why do we use CDCl instead of CHCl, for acquiring our NMR spectra? 3. Why does it not matter which enantiomer of carvone is used for this reaction? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAssign this H NMRarrow_forwardPlease complete these blanks need that asaparrow_forward
- Nitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAspirin from Wintergreen: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4. 3. Calculate the exact monoisotopic mass of aspirin showing your work. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Synthesis of Ibuprofen-Part 1: 1. What characteristic absorption band changes would you expect in the IR spectrum on going from p-isobutylacetophenone to 1-(4-isobutylphenyl)-ethanol and then to 1-(4-isobutylphenyl)-1-choroethane as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. Given that the mechanism of the chlorination reaction today involves formation of a benzylic carbocation, explain why the following rearranged product is not formed. محرم محمد 3. Why do we use dilute HCl for the first step of the reaction today and concentrated HCI for the second step? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAssign only the C NMRarrow_forwardDraw out the SALCs of wach orbital in a AlCl3 molecule.arrow_forward
- Which of the following is 3-ethyl-2-methylpentane? хarrow_forwardCan you please help me with this problem and explain it step by step? I'm so confused about itarrow_forward2. Identify the reagents you would need to achieve the following. You may need to consider using a protecting group. HO 1. 2. 3. 4. 5. OH Br HOarrow_forward
- Introductory Chemistry: An Active Learning Approa...ChemistryISBN:9781305079250Author:Mark S. Cracolice, Ed PetersPublisher:Cengage Learning
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