Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 4.SE, Problem 26VC
Interpretation Introduction
Interpretation:
The difference between alpha and beta glucose is to be found out.
Concept introduction:
Glucose can form either five-membered or six-membered rings. The six-membered ring is much more common, and in solution the vast majority of glucose molecules are found to have six-membered rings.
Each molecule of glucose has a carbon backbone with -OH groups and hydrogen atoms attached to it. At the top of the chain, an oxygen atom is double-bonded to a carbon atom; collectively, these two atoms are called a carbonyl group. The carbon backbone of the glucose molecule can coil up so that an -OH group near the bottom end of the chain attacks the carbonyl carbon and the glucose molecule forms a ring. This ring-shaped structure is the cyclic form of glucose, while the straight chain structure is the linear form.
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a. In an aqueous solution, d-glucose exists in equilibrium with two six-membered ring compounds. Draw the structures of these compounds.b. Which of the six-membered ring compounds will be the major product?
Convert the structure below to a skeletal drawing.
You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
Answer all the subparts pertaining to question 4
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- There are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forwardWhich of the following is true of compounds I and II ? CI НЕ Imm CH₂CH₂ CI CH₂CH3 I CI CI CH₂CH3 H CH₂CH3 || Select one: O A. Their boiling points are different. OB. Their melting points are the same. OC. I is optically active. Il is not. O D. They are enantiomers. O E. They are constitutional isomers.arrow_forwardCertain omega-3 fatty acids can be found only in animal sources, such as fatty fish. Two of these are eicosapentaenoic acid (EPA) [20:5] and docosahexaenoic acid (DHA) [22:6], both of which are ω-3 fatty acids. DHA has been shown to be important in healthy brain development, so it has recently been added to infant formulas. Breast milk is rich in DHA as long as the mother maintains a healthy diet that includes fish. Draw skeletal structures of the fatty acids EPA and DHA.arrow_forward
- The following are representations of two forms of glucose. The six-membered ring is known to exist in a chair conformation in each form. Draw clear representations of the most stable conformation of each. Are they two different conformations of the same molecule, or are they stereoisomers that cannot be interconverted by rotation about single bonds? Which substituents (if any) occupy axial sites?arrow_forwardIntramolecular H-bonding (IHB) are interactions that occur within one single molecule. IHB is also known as chelation, since it involves ring formation. Which of the following is (are) stabilized by IHB? * QH Çi OH -NO2 (a) Cl-Ç–Ç–H (b) či ÓH OH (с) CH, —С—СH—С—ОС,Н, CH,OH (d) | CH,OH D B Aarrow_forwardPlease answer all of it. If not, please skip. Draw the structure of a branched hydrocarbon that also contains at least one atom with trigonal planar geometry. Draw the structure of an aromatic hydrocarbon containing two halogens. Draw the structure of a molecule containing an aliphatic primary amine and a carboxyl group. Draw the structure of an acyclic molecule containing a primary and a secondary alcohol group. Draw the structure of an achiral tertiary alcoholarrow_forward
- For rotation about the C-a – C-b bond, using the following templates, draw the Newman Projection of the two staggered conformers that are different in energy. Fill each bond on Newman Projection with Hydrogen or Substituents. You may use Abbreviations such as Me for Methyl, Et for Ethyl, iPr for isopropyl. Circle the Newman projection of the most stable conformer.arrow_forward2arrow_forwardClassifying Compounds as Stereoisomers or Different Conformations Classify each pair of compounds as stereoisomers or conformations: (a) X and Y; (b) X and Z.arrow_forward
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