
Concept explainers
(a)
Interpretation:
The R or S configuration of the chiral center in the given molecule is to be designated.
Concept introduction:
When assigning priorities to substituents, the atom having the greater
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.

Answer to Problem C.10P
The configuration of the chiral carbon atom in the given molecule is designated as S.
Explanation of Solution
The given molecule is
The IUPAC name for the above molecule, without considering the stereochemistry, would be
There is one chiral center in this molecule, and the substituents attached to it are
In the structure, the
The second and third position priorities are decided by the set of atoms one bond away from the respective points of attachment. The set for the ethyl substituent, which is located on the right, is
The configuration at the chiral center of the molecule is designated as above.
(b)
Interpretation:
The R or S configuration of the chiral center in the given molecule is to be designated.
Concept introduction:
When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets the higher priority. Substituents with double/triple bonds are treated differently from the substituents having only single bonds. An atom that is doubly bonded to another atom is treated as having two single bonds to the atom – one real (shown in black) and one imaginary (shown in red). An atom that is triply bonded to another atom is treated as having three single bonds to the atom – one real (shown in black) and two imaginary (shown in red).
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.

Answer to Problem C.10P
The configuration of the chiral carbon atom in the given molecule is designated as R.
Explanation of Solution
The given molecule is
The IUPAC name for the above molecule, without considering the stereochemistry, would be
There is one chiral center in this molecule, and the substituents attached to it are
The first three top-priority substituents are decided by the set of atoms one bond away from the respective points of attachment. The set for the substituent, which is located on the right, is
The configuration at the chiral center of the molecule is designated as above.
(c)
Interpretation:
The R or S configuration of the chiral center in the given molecule is to be designated.
Concept introduction:
When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets the higher priority. Substituents with double/triple bonds are treated differently from the substituents having only single bonds. An atom that is doubly bonded to another atom is treated as having two single bonds to the atom – one real (shown in black) and one imaginary (shown in red). An atom that is triply bonded to another atom is treated as having three single bonds to the atom – one real (shown in black) and two imaginary (shown in red).
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.

Answer to Problem C.10P
The configuration of the chiral carbon atom in the given molecule is designated as R.
Explanation of Solution
The given molecule is
The IUPAC name for the above molecule, without considering the stereochemistry, would be
The second and third priority substituents are decided by the set of atoms one bond away from the respective points of attachment. The set for the substituent, which is located on the right, is
The configuration at the chiral center of the molecule is designated as above.
(d)
Interpretation:
The R or S configuration of the chiral center in the given molecule is to be designated.
Concept introduction:
When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets the higher priority. Substituents with double/triple bonds are treated differently from the substituents having only single bonds. An atom that is doubly bonded to another atom is treated as having two single bonds to the atom – one real (shown in black) and one imaginary (shown in red). An atom that is triply bonded to another atom is treated as having three single bonds to the atom – one real (shown in black) and two imaginary (shown in red).
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.

Answer to Problem C.10P
The configuration of the chiral carbon atom in the given molecule is designated as R.
Explanation of Solution
The given molecule is
The molecule contains two triple bonds. There is one chiral center in this molecule, and the substituents attached to it are
The top three-priorities are decided by the set of atoms one bond away from the respective points of attachment.
The set for the substituent, which is located on the right, is
Given that these substituents are arranged in the counterclockwise manner, but since the fourth-priority substituent is attached by a wedge bond, the arrangement is considered as reverse, that is, clockwise, and the configuration at the chiral center is R. Thus, the configuration at the chiral center for the molecule is R.
The configuration at the chiral center of the molecule is designated as above.
(e)
Interpretation:
The R or S configuration of the chiral center in the given molecule is to be designated.
Concept introduction:
When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets the higher priority. Substituents with double/triple bonds are treated differently from the substituents having only single bonds. An atom that is doubly bonded to another atom is treated as having two single bonds to the atom – one real (shown in black) and one imaginary (shown in red). An atom that is triply bonded to another atom is treated as having three single bonds to the atom – one real (shown in black) and two imaginary (shown in red).
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.

Answer to Problem C.10P
The configuration of the chiral carbon atom in the given molecule is designated as R.
Explanation of Solution
The given molecule is
The molecule contains one double bond and one triple bond. There is one chiral center in this molecule, and the substituents attached to it are
The second and third priority substituents are decided by the set of atoms one bond away from the respective points of attachment. The set for the substituent, which is located on the right, is
The configuration at the chiral center of the molecule is designated as above.
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Chapter C Solutions
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
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