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
Question
Chapter 25, Problem 25.31P
Interpretation Introduction
Interpretation:
When methyl-β-D-glucopyranoside is treated with benzaldehyde, it forms a six membered cyclic acetal. The stable conformation of this acetal has to be drawn and the new chiral centre has to be identified.
Concept Introduction:
The benzaldehyde molecule is used as a protecting agent for some reactions. In methyl-β-D-glucopyranoside the benzaldehyde acts as protecting group for C4 and C6
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Draw the organic products formed when each compound is treated with H2, Pd-C. Indicate the three-dimensional structure of all stereoisomers formed.
Aldehydes and ketones react with thiols to yield thioacetals, just as they react with alcohols to yield acetals. Draw the structure of the third intermediate in this reaction.
H* catalyst
.SCH3
+ 2 CH3SH
SCH3
Draw reaction of an aldehyde or a ketone with a thiol forms a thioacetal, and desulfurization of a thioacetal forms an alkane.
Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 25.1PCh. 25.2 - Prob. 25.2PCh. 25.2 - Prob. 25.3PCh. 25.3 - Prob. 25.4PCh. 25.3 - Prob. 25.5PCh. 25.3 - Prob. AQCh. 25.3 - Prob. BQCh. 25.3 - Prob. CQCh. 25.3 - Prob. DQCh. 25.3 - How many stereoisomers would result from the...
Ch. 25.4 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10PCh. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Prob. 25.31PCh. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Prob. 25.34PCh. 25 - In making candy or sugar syrups, sucrose is boiled...Ch. 25 - Prob. 25.36PCh. 25 - Prob. 25.37PCh. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - Prob. 25.41PCh. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Digitalis is a preparation made from the dried...Ch. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50P
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
- Many insects utilize cyclic ketal structures as pheromones such as the structure shown below. The biosynthetic pathway involves the cyclization of this acetal from the straight chain structure. Draw the straight chain structure that could be used to form this acetal. Use wedges and dashes to correctly depict the stereochemistry. H3C- >arrow_forwardDraw the products formed when each compound is treated with CH3CH2COCl, AlCl3.arrow_forward4. Draw the following compounds: 7-iodo-5-methyl-N-propylnon-2-yn-4-amine: 1-chloro-3-isopropylhex-4-en-2-ol 3-tert-butyl-4-(2-methoxyethyl)cyclopentanolarrow_forward
- Click the "draw structure" button to launch the drawing utility. Draw the product formed when the following a.f-unsaturated ketone is treated with [1] (CH,-CH),CuLi; [2] H,O. draw structure .arrow_forwardDraw the product formed when pentanal (CH3CH2CH2CH2CHO) is treated with each reagent. With some reagents, no reaction occurs.arrow_forwardcyclohexanone + piperidinearrow_forward
- In the following reaction, a primary alcohol is fully oxidized to a carboxylic acid. Draw the aldehyde intermediate that was formed.arrow_forwardDraw the product of the reaction between a ketone and an alcohol. Include all hydrogen atoms in the product. How would you classify the product of the reaction? Note that a hemiacetal formed from a ketone is also called a hemiketal; an acetal formed from a ketone is also called a ketal. The product is an alcohol. The product is a ketal The product is a ketone. The product is a hemiketal.arrow_forward3. Imitation vanilla extract contains vanillin and propylene glycol. Analysis via GC-MS shows a small quantity of a racemic mixture of a vanillin-propylene glycol acetal. Draw the structure of this acetal (considering stereochemistry) and briefly explain why it is racemic. HO H3CO vanillin H HO OH propylene glycolarrow_forward
- Draw the product formed when (CH3CH2CH2CH2)2CuLi is treated with each compound. In some cases, no reaction occurs.arrow_forwardWhich of the following statements is correct with regard to the structure of retinol? Retinol is a vitamin that plays an important role in eye function. The structure of retinol is shown below. H3C CH3 CH3 CH3 CH3 Select one: O Retinol is a diastereoisomer O Retinol is a chiral compound O Retinol is a meso compound O Retinol is an achiral compound OH Next pagearrow_forwardDraw the product formed when pentanal (CH3CH2CH2CH2CHO) is treatedwith following reagent. With some reagents, no reaction occurs. [1] HC≡CNa; [2] H2Oarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher: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