(a)
Interpretation:
For each of the given compounds, whether it is D or L sugar should be determined, the configuration of each chiral center should be assigned and the trend on the configuration of each chiral center should be explained.
Concept introduction:
- The stereo-descriptor used for carbohydrates is D or L. it is based on the dextrorotatory or levorotatory of smallest carbohydrate glyceraldehyde (1 chiral center).
The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
- The D-configuration is needed not to be dextrorotatory; rather it means the chirality center of farthest from aldo-group is having R-configuration or the –OH group is on right side.
To identify: the given carbohydrate (a) is D or L sugar and the configuration of each chiral center.
(b)
Interpretation:
For each of the given compounds, whether it is D or L sugar should be determined, the configuration of each chiral center should be assigned and the trend on the configuration of each chiral center should be explained.
Concept introduction:
- The stereo-descriptor used for carbohydrates is D or L. it is based on the dextrorotatory or levorotatory of smallest carbohydrate glyceraldehyde (1 chiral center).
The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
- The D-configuration is needed not to be dextrorotatory; rather it means the chirality center of farthest from aldo-group is having R-configuration or the –OH group is on right side.
To identify: the given carbohydrate (b) is D or L sugar and the configuration of each chiral center.
(c)
Interpretation:
For each of the given compounds, whether it is D or L sugar should be determined, the configuration of each chiral center should be assigned and the trend on the configuration of each chiral center should be explained.
Concept introduction:
- The stereo-descriptor used for carbohydrates is D or L. it is based on the dextrorotatory or levorotatory of smallest carbohydrate glyceraldehyde (1 chiral center).
The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
- The D-configuration is needed not to be dextrorotatory; rather it means the chirality center of farthest from aldo-group is having R-configuration or the –OH group is on right side.
To identify: the given carbohydrate (c) is D or L sugar and the configuration of each chiral center.
(d)
Interpretation:
For each of the given compounds, whether it is D or L sugar should be determined, the configuration of each chiral center should be assigned and the trend on the configuration of each chiral center should be explained.
Concept introduction:
- The stereo-descriptor used for carbohydrates is D or L. it is based on the dextrorotatory or levorotatory of smallest carbohydrate glyceraldehyde (1 chiral center).
The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
- The D-configuration is needed not to be dextrorotatory; rather it means the chirality center of farthest from aldo-group is having R-configuration or the –OH group is on right side.
To identify: the given carbohydrate (d) is D or L sugar and the configuration of each chiral center.
(e)
Interpretation:
For each of the given compounds, whether it is D or L sugar should be determined, the configuration of each chiral center should be assigned and the trend on the configuration of each chiral center should be explained.
Concept introduction:
- The stereo-descriptor used for carbohydrates is D or L. it is based on the dextrorotatory or levorotatory of smallest carbohydrate glyceraldehyde (1 chiral center).
The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
- The D-configuration is needed not to be dextrorotatory; rather it means the chirality center of farthest from aldo-group is having R-configuration or the –OH group is on right side.
To identify: the given carbohydrate (e) is D or L sugar and the configuration of each chiral center.
(f)
Interpretation:
For each of the given compounds, whether it is D or L sugar should be determined, the configuration of each chiral center should be assigned and the trend on the configuration of each chiral center should be explained.
Concept introduction:
- The stereo-descriptor used for carbohydrates is D or L. it is based on the dextrorotatory or levorotatory of smallest carbohydrate glyceraldehyde (1 chiral center).
The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
- The D-configuration is needed not to be dextrorotatory; rather it means the chirality center of farthest from aldo-group is having R-configuration or the –OH group is on right side.
To explain: the trend on the configuration of each chiral center in each given carbohydrates.
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Chapter 24 Solutions
ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)
- Use the literature Ka value of the acetic acid, and the data below to answer these questions. Note: You will not use the experimental titration graphs to answer the questions that follow. Group #1: Buffer pH = 4.35 Group #2: Buffer pH = 4.70 Group #3: Buffer pH = 5.00 Group #4: Buffer pH = 5.30 Use the Henderson-Hasselbalch equation, the buffer pH provided and the literature pKa value of acetic acid to perform the following: a) calculate the ratios of [acetate]/[acetic acid] for each of the 4 groups buffer solutions above. b) using the calculated ratios, which group solution will provide the best optimal buffer (Hint: what [acetate]/[acetic acid] ratio value is expected for an optimal buffer?) c) explain your choicearrow_forwardHow would you prepare 1 liter of a 50 mM Phosphate buffer at pH 7.5 beginning with K3PO4 and 1 M HCl or 1 M NaOH? Please help and show calculations. Thank youarrow_forwardDraw the four most importantcontributing structures of the cation intermediate thatforms in the electrophilic chlorination of phenol,(C6H5OH) to form p-chlorophenol. Put a circle aroundthe best one. Can you please each step and also how you would approach a similar problem. Thank you!arrow_forward
- A 100mM lactic acid/lactate buffer was found to have a lactate to lactic acid ratio of 2 and a pH of 4.2. What is the pKa of lactic acid? Can you please help show the calculations?arrow_forwardUsing line angle formulas, draw thestructures of and name four alkanes that have total of 7carbons, one of which is tertiary.Please explain this in detail and can you also explain how to approach a similar problem like this as well?arrow_forwardUsing dashed line wedge projections drawthe indicated compounds and indicate whether thecompound you have drawn is R or S.(a) The two enantiomers of 2-chlorobutane. Can you please explain your steps and how you would approach a similar problem. Thank you!arrow_forward
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