Concept explainers
(a)
Interpretation:
The chair conformation of the compound
Concept introduction:
The saturated six membered ring compounds are mostly expressed and explained in the chair conformations. This is because chair conformation is the most stable conformation of cyclohexane. Therefore, the chair conformation is most helpful in the study of six carbon ring compounds.
(b)
Interpretation:
The reason as to why
Concept introduction:
Glucose is an organic compound having the molecular formula of
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Chapter 24 Solutions
Organic Chemistry
- 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.arrow_forwardFollowing is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see Chemical Connections: A, B, AB, and O Blood Group Substances in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.arrow_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_forward
- D-Mannose differs in configuration from D-glucose at carbon-2. Draw chair conformations for α-D-mannopyranose and β-D-mannopyranose. Label the anomeric carbon in each.arrow_forwardWhat is the correct assignment of chirality at C2 and C4 for the following moleculearrow_forwarda) Draw a 2-dimensional structure of 4,5-dibromooctane and label, with an asterisk, thetetrahedral stereo centers.b) What is the maximum number of stereoisomers for this molecule?c) Draw Fischer projections of all the potential stereoisomers of (a).d) Label, on the above projections, all the stereocenters as R or S.e) Indicate the enantiomers, diastereomers and the meso compound if present.arrow_forward
- In the most stable chair conformation of myo-Inositol, how many of the OH groups are axial and how many are equatorial?arrow_forwardDraw all possible configurational stereoisomers for the given molecule below. Designate the R/S on the stereogenic centers and E/Z on the C=Carrow_forward1. draw the most stable chair form of (1R,2R)-1-ethyl-2-methylcyclohexane 2. in the following chiral compound, the stereogenic center is denoted by C*. assign the priorities to the groups attached to C* using the Cahn-Ingold-Prelog system. please show your work (the image goes with question 2)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning