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Concept explainers
(a)
Interpretation: The four possible stereoisomers of threonine by using wedges and dashes are to be drawn.
Concept introduction: Isomers are the compounds with similar formula and different structures. Stereoisomers are a type of isomers in which arrangement of atoms differ in space. Or the compounds that have same molecular formula but they differ in the arrangement of atoms or groups in the space are known as stereoisomers.
(b)
Interpretation: The structure which corresponds to an amino acid with
Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of
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Chapter 19 Solutions
Organic Chemistry
- 43. Specify expressions specific to panaxosides. I. taken from ginseng II. there are glucose and arabinose monosaccharides in this compound III. taken from Japanese angelica-tree IV. tetratcyclic triterpen saponins V. spirostanol type glycoside VI. dimer structure VII. biglycosides VIII. dammaran group IX. differ for number of hydroxyl groups X. furostanol type glycoside A) II; VI; VII; IX; X B) III; V; VIII C) I; IV; VIII; IX D) I; VIII; IX E) I; III; V; VII; VIII; Xarrow_forward3) Give an example of: a. A compound with 2 or more stereocenters that is superimposable on its mirror image. b. A pair of compounds that are chiral but are non-superimposable and non-mirror images. c. A pair of compounds with 2 or more stereocenters that are non-superimposable and mirror images.arrow_forwardConsider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.a. Label all glycoside bonds.b. Classify each glycosidic linkage as α or β and use numbers to designate its location between two rings (e.g., 1→4-β).c. What products are formed when stachyose is hydrolyzed with H3O+?d. Is stachyose a reducing sugar?e. What product is formed when stachyose is treated with excess CH3I, Ag2O?f. What products are formed when the product in (e) is treated with H3O+?arrow_forward
- Threonine is a naturally occurring amino acid that has two stereogenic centers.a. Draw the four possible stereoisomers using wedges and dashed wedges.b. The naturally occurring amino acid has the 2S,3R configuration at its two stereogenic centers. Which structure does this correspond to?arrow_forwardWhich monosaccharide is a-glucose? CH,OH CH,OH CH;OH CH,OH H. H. OH H. OH HO. H. OH H. H. H. HO. H. OH H. H. H. OH H. H. H. OH H. H. H. H. H. C OD O B O C OA A,arrow_forwardConsider the structure below: HOH H. но H. H- H. он он он HO. H. H. OH O H. HO он H- H. он H. Is the trisaccharide a reducing sugar? [ Choose ] Identify the type of glycosidic linkage of the [Choose ] colored bond.arrow_forward
- 1. Which sugars are reducing? Which sugars are non-reducing? a. Glucose: b. Fructose: c. Sucrose: d. Lactose: e. Sucrose hydrolysate: Starch hydrolysate: g. Cellulose hydrolysate: f. 2. What structural feature is responsible for the reducing property of carbohydrates?arrow_forwardThe amino acid (S)-alanine has the physical characteristics listed under the structure. a. What is the melting point of (R)-alanine? b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine? c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine? d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine? e. Label each of the following as optically active or inactive: a solution of pure (S)- alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine. HO, NH2 (S)-alanine [a] = +8.5 mp = 297 °Carrow_forward3. HO" он HO. но, но HO OH Solanine Solanine is a naturally occurring compound that contain glycoside bonds as part of its structure. Determine the structure of aglycon and monosaccharides fomed when solanine is hydrolyzed with aqueous acid. Include all the appropriate anomers.arrow_forward
- The amino acid (S)-alanine has the physical characteristics listed under the structure. a.What is the melting point of (R)-alanine? b.How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine? c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine? d.What is the optical rotation of a racemic mixture of (R)- and (S)-alanine? e.Label each of the following as optically active or inactive: a solution of pure (S)alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.arrow_forwardConsider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.a. Label all glycoside bonds.b. Classify each glycosidic linkage as αα or ββ and use numbers to designate its location between two rings (e.g., 1→→4-ββ)-c. What products are formed when stachyose is hydrolyzed with H33O++?d. Is stachyose a reducing sugar?e. What product is formed when stachyose is treated with excess CH33I, Ag22O?f. What products are formed when the product in (e) is treated with H33O++?arrow_forwardFrom the choices given below select the aldohexose that yields the same alditol as L-mannose upon reduction with NaBH4. Select ALL monosaccharides that satisfy the requirement, excluding the structure referenced in the question. Note that only D structures are shown. To select an L structure click on the name. If no selection exists, then select the referenced structure. H H- H H CHO -OH HO- -OH H -OH H -OH H CH₂OH D-Allose L-Allose CHO -H H OH HO- -OH H -OH H- CH₂OH D-Altrose L-Altrose CHO CH₂OH D-Glucose CHO OH HO -H -H HO- -H H- OH H -OH HO- -OH H-+ OH H L-Glucose CH₂OH D-Mannose H- L-Mannose CHO OH OH H -H HO OH H- CH₂OH D-Gulose L-Gulose HO CHO -H H- -OH HO- -H HO- -OH H CH₂OH D-Idose L-Idose CHO OH HO -H HO- -H HO -OH CH₂OH D-Galactose L-Galactose H- CHO -H -H -H -OH CH₂OH D-Talose L-Talosearrow_forward
- Introductory Chemistry: An Active Learning Approa...ChemistryISBN:9781305079250Author:Mark S. Cracolice, Ed PetersPublisher:Cengage Learning
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