ORGANIC CHEM ALC&STU S/G&S W/MASTER CHE
8th Edition
ISBN: 9780134581583
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20, Problem 73P
Interpretation Introduction
Interpretation:
The explanation corresponding to the given statement that
Concept Introduction:
The chair conformers are stable forms of cyclic compounds. In chair conformation, substituent’s prefers to place at equatorial positions. This is due to unwanted interactions between those substituent’s that are placed at axial positions. These interactions cause repulsion and that leads to the un-stability in molecule. The general interactions that occur between axial substituents are
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react toform an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of d-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of d-glucose exists in the anhydro form under the same conditions.
When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react to form an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of D-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of D-glucose exists in the anhydro form under the same conditions.
Convert the following chair conformation of the sugar beta-D-galactose into a structure that shows all via and trans relationships.
Chapter 20 Solutions
ORGANIC CHEM ALC&STU S/G&S W/MASTER CHE
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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.arrow_forwardDraw the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimersarrow_forwardA) Draw the structure of any aldohexose in the pyranose ring form. B) Draw the structure of the anomer of the aldohexose you drew above. C) How many asymmetric carbons (chiral centers) does each of these structures have? D) How many stereoisomers of the aldohexoses you drew are theoretically possible?arrow_forward
- When 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_forwardAn important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.arrow_forwarddoes structure E represent fructofuranose? explainarrow_forward
- Draw the cyclic hemiacetal forms of d-mannose and d-galactose both as chair conformations and as Haworth projections. Mannose is the C2 epimer of glucose, and galactoseis the C4 epimer of glucose.arrow_forwardHow many chiral centers are in B-d-glucopyranose and a-D-galactopyranose? How many stereoisomers of these two aldohexoses can theoretically be drawn?arrow_forward5-Deoxyglucose will close to a?arrow_forward
- How many stereoisomers are possible for an aldopentose?arrow_forwardDraw the Fischer, the Haworth, and the most stable chair conformation (equatorial vs axial) of β-D-mannose. Please number your carbons. Please draw it by hand and not by the internet through screen shot. Please explain. Thank you!arrow_forwardAnswer the following questions about the eight aldopentoses: a. Which are enantiomers? b. Which are C-2 epimers? c. Which form an optically active compound when oxidized with nitric acid?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning