ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
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Question
Chapter 2, Problem 2.37P
Interpretation Introduction
(a)
Interpretation:
The structure of D-glucose using dash-wedge notation, after the given indicated rotation has taken place, is to be drawn.
Concept introduction:
Dash-wedge notations are used to represent the three dimensional molecular geometry; a wedge line represents the bond pointing towards the observer whereas a dash line represents the bond pointing away from the observer. The bonds that are in plane are represented by a straight line. A
Interpretation Introduction
(b)
Interpretation:
The structure of D-glucose using dash-wedge notation, after the given indicated rotation has taken place, is to be drawn.
Concept introduction:
Dash-wedge notations are used to represent the three dimensional molecular geometry; a wedge line represents the bond pointing towards the observer whereas a dash line represents the bond pointing away from the observer. The straight line represents that the bond is in the plane of paper.
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Calculate the percentages of α-d-glucose and b-d-glucose present at equilibrium from the specific rotations of a-d-glucose, β-d-glucose, and the equilibrium mixture. Compare your values with those given in Section 20.10. (Hint: The specific rotation of the mixture equals the specific rotation of α-d-glucose times the fraction of glucose present in the a-form plus the specific rotation of β-d-glucose times the fraction of glucose present in the β-form.)
Draw Fischer projections for five aldoses below: glucose, mannose, galactose, arabinose and
xylose. Now draw Fischer projections for the reduced and acetylated derivatives of these
aldoses. From the Fischer drawings, select the meso molecules and redraw them, this time
adding a plane of symmetry. Then select the molecules having an axis of symmetry, this time
adding a line that skewers the middle of the drawing to indicate this symmetry.
Utilize the carbohydrate provided to answer each part below. a. On the Fischer projection, clearly circle the penultimate carbon. b. Circle the appropriate name listed below that corresponds to the structure.• D-aldopentose • D-aldohexose • D-ketopentose • D-ketohexose • L-aldopentose • L-aldohexose • L-ketopentose • L-ketohexose
Chapter 2 Solutions
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
Ch. 2 - Prob. 2.1PCh. 2 - Prob. 2.2PCh. 2 - Prob. 2.3PCh. 2 - Prob. 2.4PCh. 2 - Prob. 2.5PCh. 2 - Prob. 2.6PCh. 2 - Prob. 2.7PCh. 2 - Prob. 2.8PCh. 2 - Prob. 2.9PCh. 2 - Prob. 2.10P
Ch. 2 - Prob. 2.11PCh. 2 - Prob. 2.12PCh. 2 - Prob. 2.13PCh. 2 - Prob. 2.14PCh. 2 - Prob. 2.15PCh. 2 - Prob. 2.16PCh. 2 - Prob. 2.17PCh. 2 - Prob. 2.18PCh. 2 - Prob. 2.19PCh. 2 - Prob. 2.20PCh. 2 - Prob. 2.21PCh. 2 - Prob. 2.22PCh. 2 - Prob. 2.23PCh. 2 - Prob. 2.24PCh. 2 - Prob. 2.25PCh. 2 - Prob. 2.26PCh. 2 - Prob. 2.27PCh. 2 - Prob. 2.28PCh. 2 - Prob. 2.29PCh. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - Prob. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - Prob. 2.37PCh. 2 - Prob. 2.38PCh. 2 - Prob. 2.39PCh. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 2 - Prob. 2.45PCh. 2 - Prob. 2.46PCh. 2 - Prob. 2.47PCh. 2 - Prob. 2.48PCh. 2 - Prob. 2.49PCh. 2 - Prob. 2.50PCh. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - Prob. 2.54PCh. 2 - Prob. 2.55PCh. 2 - Prob. 2.56PCh. 2 - Prob. 2.57PCh. 2 - Prob. 2.58PCh. 2 - Prob. 2.59PCh. 2 - Prob. 2.60PCh. 2 - Prob. 2.61PCh. 2 - Prob. 2.62PCh. 2 - Prob. 2.63PCh. 2 - Prob. 2.64PCh. 2 - Prob. 2.65PCh. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - Prob. 2.68PCh. 2 - Prob. 2.69PCh. 2 - Prob. 2.70PCh. 2 - Prob. 2.71PCh. 2 - Prob. 2.72PCh. 2 - Prob. 2.1YTCh. 2 - Prob. 2.2YTCh. 2 - Prob. 2.3YTCh. 2 - Prob. 2.4YTCh. 2 - Prob. 2.5YTCh. 2 - Prob. 2.6YTCh. 2 - Prob. 2.7YTCh. 2 - Prob. 2.8YTCh. 2 - Prob. 2.9YTCh. 2 - Prob. 2.10YTCh. 2 - Prob. 2.11YTCh. 2 - Prob. 2.12YTCh. 2 - Prob. 2.13YTCh. 2 - Prob. 2.14YTCh. 2 - Prob. 2.15YTCh. 2 - Prob. 2.16YTCh. 2 - Prob. 2.17YTCh. 2 - Prob. 2.18YTCh. 2 - Prob. 2.19YTCh. 2 - Prob. 2.20YT
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- Mannose exists in aqueous solution as a mixture of a-d-mannopyranose and b-d-mannopyranose. Draw Haworth projections for these molecules.arrow_forwardWhen a crystalline sample of α-glucopyranose is dissolved in water and the specific rotation is measured immediately, the observed rotation is +112°. When the same amount of βglucopyranose is dissolved, the observed rotation is +18.7°. However, over time, at room temperature, both solutions reach a specific rotation of +52.7°. Explain why these two solutions reach the same specific rotation over time.arrow_forwardThe specific rotation of α-d-galactose is 150.7 and that of β-d-galactose is 52.8. When an aqueous mixture that was initially 70% α-d-galactose and 30%β-d-galactose reaches equilibrium, the specific rotation is 80.2. What is the percentage of α-d-galactose and β-d galactose at equilibrium?arrow_forward
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- Without referring to the chapter, draw the chair conformations of(a) b-d-mannopyranose (the C2 epimer of glucose).(b) a-d-allopyranose (the C3 epimer of glucose).(c) b-d-galactopyranose (the C4 epimer of glucose)arrow_forwardWhich anomer of this carbohydrate is shown in this picture? Enter the word “alpha” or “beta” in the space provided below.arrow_forwardPlease draw the expanded structure of D-tagatose and its Fischer Projection (chiral C represented as a cross).arrow_forward
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