Stereochemistry in biological molecules is often denoted by the D- and L- convention, instead of the R- and S- configurations determined by the Cahn-Ingold-Prelog methodology. Historically, the glyceraldehyde enantiomer that rotated plane polarized light clockwise was arbitrarily designated as D and the other enantiomer was designated as the L configuration. The D-glyceraldehyde Fischer projection is shown. D-glyceraldehyde H H- -OH CH₂OH Identify which structures are equivalent to the D-configuration. H CH₂OH 76. OH CH₂OH H- -OH ☐ O H ОН -CH₂OH K H H Incorrect HOCH2 H OH t H OH CH₂OH K.

Stereochemistry in biological molecules is often denoted by the D- and L- convention, instead of the R- and S- configurations determined by the Cahn-Ingold-Prelog methodology. Historically, the glyceraldehyde enantiomer that rotated plane polarized light clockwise was arbitrarily designated as D and the other enantiomer was designated as the L configuration. The D-glyceraldehyde Fischer projection is shown. D-glyceraldehyde H H- -OH CH₂OH Identify which structures are equivalent to the D-configuration. H CH₂OH 76. OH CH₂OH H- -OH ☐ O H ОН -CH₂OH K H H Incorrect HOCH2 H OH t H OH CH₂OH K.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.SE: Something Extra

Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...

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Stereochemistry in biological molecules is often denoted by the D‑ and L‑ convention, instead of the ?‑R‑ and ?‑S‑ configurations determined by the Cahn–Ingold–Prelog methodology. Historically, the glyceraldehyde enantiomer that rotated plane polarized light clockwise was arbitrarily designated as D and the other enantiomer was designated as the L configuration. The D‑glyceraldehyde Fischer projection is shown. D‑glyceraldehyde
a）Draw all other stereoisomers of the molecule, labelling meso forms (if any), and assign descriptors to chiral carbon atoms. (b) Including molecule, label pairs of enantiomers and pairs of diastereomers. (c) If you were to distill a mixture of all the isomers, how many fractions could be obtained, and what would in each fraction?
Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.
Determine the absolute configuration of the following compounds anddraw the structure (Fischer projection) of the other enantiomer.
Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)
Stereochemistry in biological molecules is often denoted by the D‑ and L‑ convention, instead of the ?‑ and ?‑ configurations determined by the Cahn–Ingold–Prelog methodology. Naturally occurring α‑amino acids are typically in the L‑configuration. The Fischer projection of L‑alanine is shown. L‑alanine Identify which structures are equivalent to the L‑configuration.
Find an example of a chiral molecule in biology whose enantiomers have markedly different functions. Where is the chiral center located, and how can it be identified? Find and include an image of its molecular structure. What function does the active enantiomer play biologically, and how is this function hindered or changed with the other enantiomer? Are there any synthetic considerations for this molecule?
If the two stereogenic centers of a compound are R,S in configuration, what are the R,S assignments for its enantiomer and two diastereomers?
Explain the observed stereochemistry. When the second intermediate is redrawn from the following perspective, it becomes clear that O the electrons in the carbon-carbon-bond come from above the carbon-oxygen bond, allowing for the chirality center to be generated with the stereochemistry shown. O the electrons in the carbon-oxygen-bond come from above the carbon-carbon bond, allowing for the chirality center to be generated with the stereochemistry shown. the electrons in the carbon-carbon-bond come from below the carbon-oxygen bond, allowing for the chirality center to be generated with the stereochemistry shown. O the electrons in the carbon-oxygen-bond come from below the carbon-carbon bond, allowing for the chirality center to be generated with the stereochemistry shown.
7.(a) Draw and label (a) the enantiomer and (b) a pair of diasteromers of the following compound. OH (c) Will a 50:50 mix of the enantiomers of the compound be optically active (rotate plane polarized light). Explain the reason for your answer d) Will a 50:50 mix of the two diasteriomers you drew in (c) be optically active (rotate plane polarized light). Explain the reason for your answer
The two enantiomers of a chiral compound are present in the ratio 50:25. What is the enantiomeric excess for this compound? Select one: а. 100% O b. None of the others С. 50% d. 25% е. 20%
Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.