Concept explainers
(a)
Interpretation:
The configuration of each stereocenter in the given molecule is to be designated as R or S and the IUPAC name for each molecule is to be written.
Concept introduction:
When assigning priorities to substituents, the atom having the greater
(b)
Interpretation:
The configuration of each stereocenter in the given molecule is to be designated as R or S and the IUPAC name for each molecule is to be written.
Concept introduction:
When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets the higher priority. When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R. When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S. If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S. If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then, the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.
(c)
Interpretation:
The configuration of each stereocenter in the given molecule is to be designated as R or S and the IUPAC name for each molecule is to be written.
Concept introduction:
When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets the higher priority. When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R. When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S. If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S. If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then, the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined, and that arrangement is reversed before assigning R or S. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.
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Check out a sample textbook solutionChapter C Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Answer the following question about compounds A–D (See in attachment) Label each compound as a cis or trans isomerarrow_forwardDraw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond.arrow_forwardProblem: (a) Draw six (6) constitutional isomers of C6H1202. (b) Which of the compounds you drew would be the most soluble in water? Explain your choice. (c) Which of the compounds you drew would be the most soluble in hexane? Explain your choice.arrow_forward
- Draw Newman projects of all the staggered conformations for the molecule below looking along the bolded bond in the direction indicated by the arrow. The carbon closest to the arrow should be the front carbon of your Newman projection. (It is a practice problem from the book but I am confused about how to approach it.)arrow_forwardProblem: Perform a conformational analysis 2-iodo-2-methylbutane, looking down the C2—C3 bond. Pay attention to the relative energies of the various conformations, but do not concern yourself with the actual energy values. Pleae draw newman projections.arrow_forwardAnswer the questions about the molecule shown here. H Br This molecule is shown in its most stable conformation. True False (response not displayed)arrow_forward
- Circle the compound that would have the lowest energy at its most stable conformation and box the compound that would have the highest energy at its most stable conformation.arrow_forwardFor the following pair of molecules, (1) Draw out the chair conformation for each molecule, flip the ring if it is possible. (2) Compare both molecules to circle out which one is more stable. (3) Assign the absolute configuration (R/S) on all the chiral center(s), if it applicable. (4) Name the molecule on the left side. VS.arrow_forwardFill in table with the missing information. Each molecule in each row should have a skeletal formula, an IUPAC name, and a functional class identified.arrow_forward
- Draw the Newman projections for one staggered and one eclipsed conformation of the molecule below, viewed down the indicated bond in the direction of the arrow. Cl_H Brarrow_forwardLabel the following pairs as A) distereoisomers, B) enantiomers, C) conformers, or D) the same. b1 c1 d1 e1 a2 b2 c2 The structures above are labeled a1, a2, b1, b2 ...etc. Using these labels, indicate which compounds above would have an optical rotation ofarrow_forwardComplete the following for the compound shown below. a) Draw the line structure using the wedge/dash bond convention to show the correct stereochemistry. b) Draw both chair conformations, and indicate that they are in equilibrium using appropriate arrows. c) Label the most stable structure. d) Label the most structure that is the major conformer in solution. e) Explain your answers to c) and d) as we did in class, and Loudon did in the text.arrow_forward
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