Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 16, Problem 16.67P
Treatment of β-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.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Zeroth Order Reaction
In a certain experiment the decomposition of hydrogen iodide on finely divided gold is zeroth order with respect to HI.
2HI(g) Au H2(g) + 12(9)
Rate =
-d[HI]/dt k = 2.00x104 mol L-1 s-1
If the experiment has an initial HI concentration of 0.460 mol/L, what is the concentration of HI after 28.0 minutes?
1 pts
Submit Answer Tries 0/5
How long will it take for all of the HI to decompose?
1 pts
Submit Answer Tries 0/5
What is the rate of formation of H2 16.0 minutes after the reaction is initiated?
1 pts
Submit Answer Tries 0/5
angelarodriguezmunoz149@gmail.com
Hi i need help with this question i am not sure what the right answers are.
Please correct answer and don't used hand raiting
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Write the IUPAC name for each compound. Specify...Ch. 16.1 - Write structural formulas for all aldehydes with...Ch. 16.1 - Write the IUPAC name for each compound.Ch. 16.5 - Prob. 16.4PCh. 16.6 - Prob. 16.5PCh. 16.7 - Prob. 16.6PCh. 16.7 - Write a mechanism for the acid-catalyzed...Ch. 16.8 - Prob. 16.8PCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...
Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
Additional Science Textbook Solutions
Find more solutions based on key concepts
Describe the evolution of mammals, tracing their synapsid lineage from early amniote ancestors to true mammals....
Loose Leaf For Integrated Principles Of Zoology
How does the removal of hydrogen atoms from nutrient molecules result in a loss of energy from the nutrient mol...
SEELEY'S ANATOMY+PHYSIOLOGY
Choose the best answer to each of the following. Explain your reasoning. If Earth were twice as far as it actua...
Cosmic Perspective Fundamentals
Label each statement about the polynucleotide ATGGCG as true or false. The polynucleotide has six nucleotides. ...
General, Organic, and Biological Chemistry - 4th edition
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
- Don't used hand raitingarrow_forwardDon't used Ai solutionarrow_forwardSaved v Question: I've done both of the graphs and generated an equation from excel, I just need help explaining A-B. Below is just the information I used to get the graphs obtain the graph please help. Prepare two graphs, the first with the percent transmission on the vertical axis and concentration on the horizontal axis and the second with absorption on the vertical axis and concentration on the horizontal axis. Solution # Unknown Concentration (mol/L) Transmittance Absorption 9.88x101 635 0.17 1.98x101 47% 0.33 2.95x101 31% 0.51 3.95x10 21% 0.68 4.94x10 14% 24% 0.85 0.62 A.) Give an equation that relates either the % transmission or the absorption to the concentration. Explain how you arrived at your equation. B.) What is the relationship between the percent transmission and the absorption? C.) Determine the concentration of the ironlll) salicylate in the unknown directly from the graph and from the best fit trend-line (least squares analysis) of the graph that yielded a straight…arrow_forward
- Don't used Ai solutionarrow_forwardCalculate the differences between energy levels in J, Einstein's coefficients of estimated absorption and spontaneous emission and life time media for typical electronic transmissions (vnm = 1015 s-1) and vibrations (vnm = 1013 s-1) . Assume that the dipolar transition moments for these transactions are in the order of 1 D.Data: 1D = 3.33564x10-30 C m; epsilon0 = 8.85419x10-12 C2m-1J-1arrow_forwardDon't used Ai solutionarrow_forward
- Please correct answer and don't used hand raitingarrow_forwardIn an induced absorption process:a) the population of the fundamental state is diminishingb) the population of the excited state decreasesc) the non-radiating component is the predominant oned) the emission radiation is consistentarrow_forwardhow a - Cyanostilbenes are made? provide 3 different methods for their synthesisarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License