General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 15, Problem 51P
(a) Define the terms “optically active” and “optically inactive.” (b) Give an example of a compound with molecular formula
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Explain the concept of chirality in organic chemistry, its significance in drug design, and the difference between enantiomers and diastereomers.
The structural formula for the open-chain form of
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CH
НО—С—Н
Но-с—н
Н—С—ОН
Н—ҫ—ОН
CH-OН
(a) Is this molecule a sugar? (b) How many chiral carbons
are present in the molecule? (c) Draw the structure of the
six-member-ring form of this molecule.
(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called “andro,” from the following description. Andro contains the tetracyclic steroid skeleton with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13. (b) Add wedges and dashed wedges for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.
Chapter 15 Solutions
General, Organic, and Biological Chemistry - 4th edition
Ch. 15.1 - Prob. 15.1PCh. 15.1 - Prob. 15.1PPCh. 15.1 - For trans-2-hexene: (a) draw a stereoisomer; (b)...Ch. 15.2 - Prob. 15.3PCh. 15.2 - Prob. 15.4PCh. 15.3 - Prob. 15.2PPCh. 15.3 - Prob. 15.5PCh. 15.3 - Prob. 15.6PCh. 15.3 - Prob. 15.3PPCh. 15.3 - Prob. 15.7P
Ch. 15.3 - Prob. 15.8PCh. 15.3 - Prob. 15.9PCh. 15.4 - Prob. 15.4PPCh. 15.4 - Prob. 15.10PCh. 15.4 - Prob. 15.11PCh. 15.4 - Prob. 15.12PCh. 15.5 - Prob. 15.13PCh. 15.6 - Prob. 15.5PPCh. 15.6 - Prob. 15.14PCh. 15.6 - Prob. 15.15PCh. 15.7 - Prob. 15.16PCh. 15.7 - Prob. 15.17PCh. 15.7 - Prob. 15.6PPCh. 15.7 - Prob. 15.18PCh. 15.8 - Prob. 15.7PPCh. 15.8 - Prob. 15.19PCh. 15.9 - Prob. 15.20PCh. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - Prob. 23PCh. 15 - Prob. 24PCh. 15 - Prob. 25PCh. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Prob. 28PCh. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Prob. 31PCh. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Prob. 35PCh. 15 - Prob. 36PCh. 15 - How are the compounds in each pair related? Are...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - Prob. 47PCh. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - Prob. 50PCh. 15 - (a) Define the terms “optically active” and...Ch. 15 - Prob. 52PCh. 15 - Prob. 53PCh. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - Prob. 60PCh. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Prob. 67CPCh. 15 - Prob. 68CP
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- The structural formula for the open-chain form of galactose is CH Н—ҫ—ОН Но—С—н НО—С—Н Н—ҫ—ОН CH-ОН (a) Is this molecule a sugar? (b) How many chiral carbons are present in the molecule? (C) Draw the structure of the six-member-ring form of this molecule.arrow_forwardWhich of the following statements is true for compounds A and B? H CI CI, H H CI H CI A B (A) A and B are enantiomers. (B) A and B are diastereomers. (C) A and B are constitutional isomers. (D) A and B are two conformers of the same molecule. (E) A and B are not isomers.arrow_forwardWhich statements are true about constitutional isomers? (a) They have the same molecular formula. (b) They have the same molecular weight. (c) They have the same order of attachment of atoms. (d) They have the same physical propertiesarrow_forward
- Compound Y is formed when acid reacts with alcohol: H3C CH3 (a) Identify the functional group that exist in compound Y. (b) Determine whether compound Y is optically active or not? Explain your answer (c) Draw the enantiomers of compound Y.arrow_forwardWhich compound(s) can hydrogen bond to another molecule like itself? Which compounds can hydrogen bond to water? (a) CH 3CONHCH 3; (b) HCON(CH 3) 2.arrow_forward4. (a) Draw all possible isomers of C4H3CI2. (b) Indicate which pairs of compounds are enantiomers of one another. (c) Indicate which pairs of compounds are diastereomers of one another. (d) Indicate which compounds would have optical rotations of 0°. (e) Assign R and S configurations to all chirality centers of the compounds in part (a).arrow_forward
- Cortisone is a compound that is used as an anti-inflammatory drug to treat 2) diseases like arthritis. Cortisone is a steroid which contains four rings (A, B, C and D), and has the following structure: он "OH Cortisone Provide the data to complete each of the following statements: The total number of chiral carbons (stereocentres) in Cortisone is The maximum number of stereoisomers possible is: The degree of unsaturation (IHD) of Cortisone is The total number of 2° hydrogens is The ring fusion between rings B and C is trans or cis? The absolute configuration of the carbon with * in the structure is The total number of n bonds isarrow_forwardFour stereoisomers exist for 3-penten-2-ol. (a) Explain how these four stereoisomers arise. (b) Draw the stereoisomer having the E configuration about the carbon-carbon double bond and the R configuration at the chiral center.arrow_forwardDraw the structural formulas of the following compounds:(a) 2,3-Dimethylpentanal(b) 1,3-Dibromopropanone(c) 4-hydroxy-4-methylhexan-2-onearrow_forward
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