Concept explainers
a)
Interpretation:
The Fischer projection formula is to be converted in to a tetrahedral representation and its configuration as R or S is to be assigned.
Concept introduction:
In Fischer projection formula, a tetrahedral carbon is represented by two crossed lines. The horizontal line represents bonds coming out of the page and vertical lines represent bonds moving in to the page.
For assigning R or S configuration, the four groups attached to the chiral center are arranged in the order of priority by applying sequence rules. The molecule is then oriented in such a way that the group of lowest priority points away from the viewer. If the arrangement of highest priority to second highest priority to third highest priority is clockwise then R configuration is assigned. If the arrangement of highest priority to second highest priority to third highest priority is counterclockwise then S configuration is assigned.
To covert:
The Fischer projection formula in to a tetrahedral representation and to assign its configuration as R or S.
b)
Interpretation:
The Fischer projection formula is to be converted in to a tetrahedral representation and its configuration as R or S is to be assigned.
Concept introduction:
In Fischer projection formula, a tetrahedral carbon is represented by two crossed lines. The horizontal line represents bonds coming out of the page and vertical lines represent bonds moving in to the page.
For assigning R or S configuration, the four groups attached to the chiral center are arranged in the order of priority by applying sequence rules. The molecule is then oriented in such a way that the group of lowest priority points away from the viewer. If the arrangement of highest priority to second highest priority to third highest priority is clockwise then R configuration is assigned. If the arrangement of highest priority to second highest priority to third highest priority is counterclockwise then S configuration is assigned.
To covert:
The Fischer projection formula in to a tetrahedral representation and to assign its configuration as R or S.
c)
Interpretation:
The Fischer projection formula is to be converted in to a tetrahedral representation and its configuration as R or S is to be assigned.
Concept introduction:
In Fischer projection formula, a tetrahedral carbon is represented by two crossed lines. The horizontal line represents bonds coming out of the page and vertical lines represent bonds moving in to the page.
For assigning R or S configuration, the four groups attached to the chiral center are arranged in the order of priority by applying sequence rules. The molecule is then oriented in such a way that the group of lowest priority points away from the viewer. If the arrangement of highest priority to second highest priority to third highest priority is clockwise then R configuration is assigned. If the arrangement of highest priority to second highest priority to third highest priority is counterclockwise then S configuration is assigned.
To covert:
The Fischer projection formula in to a tetrahedral representation and to assign its configuration as R or S.
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Chapter 25 Solutions
Organic Chemistry
- Consider the following compounds: CO,H СНО ОНС. ОНС CO,H H3C H. H H3C ОН ČO,H H. CH3 HỌ A B (a) Label the asymmetric carbons as R or S on each compound (A - C). (b) Which compounds, if any, are enantiomers? diastereomers? identical?arrow_forward11. Consider the following compounds: ÇO,H CHO ОНС H. ОНС CO,H H3C- -- H. HO- H3C H. O, H ČOH HO, CH3 B (a) Label the asymmetric carbons as R or S on each compound (A - C). (b) Which compounds, if any, are enantiomers? diastereomers? identical?arrow_forwardAssign R or S stereochemistry to the chirality centers in the following Newman projections Н. H3C CI Н CH3 Н H3C- H3C H Н ОН CH3arrow_forward
- A) Assign Ror S configuration to each chirality center in the following biological molecules email a OH NHH agula HN H OH Biotin HO Prostaglandin E1 B) Assign Ror S stereochemistry to the chirality centers in the following Newman projections HO CI H. CH3 X H3C H H H H3C OH + H3C CH3 Harrow_forwardOne of the following molecules (a)–(d) is d-erythrose 4-phosphate, an intermediate in the Calvin photosynthetic cycle by which plants incorporate CO2 into carbohydrates. If d-erythrose 4-phosphate has R stereochemistry at both chirality centers, which of the structures is it? Which of the remaining three structures is the enantiomer of d-erythrose 4-phosphate, and which are diastereomers?arrow_forwardWhat is the stereochemical configuration of the enantiomer of (2S, 4R)-2, 4-octanediol? (A diol is a compound with two —OH groups.)arrow_forward
- Allenes are compounds with adjacent carbon-carbon double bonds. Many allenes are chiral, even though they don’t contain chirality centers. Mycomycin, for example, a naturally occurring antibiotic isolated from the bacterium Nocardia acidophilus, is chiral and has [α]D = -130. Explain why mycomycin is chiral.arrow_forwardThe image shows Fischer projections for the structures of four isomers of a ketopentose. CH₂OH CH₂OH CH₂OH ПА пс C=O D HOEC H HOECH CH,OH A C=O H➡ COH но-с-н CH₂OH Which of the structures are stereoisomers of B? B Which of the structures are diastereomers of D? C=O HOI-C-H HOI-C-H CH₂OH с 000 ΤΑ B HO D CH₂OH O Which of the structures are enantiomers of C? H HI COH D CH₂OHarrow_forwardHow many stereoisomers are generated by the reaction below? (1) Hg(OAc)2, H20/THF (2) NABH/ethanol Oa pair of enantiomers Oa single stereoisomer a pair of diastereomers four stereoisomersarrow_forward
- 6) Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? CO20H CH3 t, H2N . CO2H WH2 CH3 7) Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? CH3 H C OH 3. HOarrow_forwardThe compound below has how many stereogenic centers (chiral carbons)? The compound below has how many Stereagenic centers (chiral carbons)? | 2 34 COE Aarrow_forwardIdentify the relationship between the following compounds. H H НО. CH3 H3C. H3C Br H Br constitutional isomer H OH CH3 O identical O diastereomers enantiomers O compounds with different molecular formulasarrow_forward
