Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter FRP, Problem 15P
Interpretation Introduction
Interpretation:
The mechanistic rationalizations of the different products on the dehalogenation of meso and enantiomeric 2,3-dibromobutane are to be demonstrated.
Concept introduction:
Meso compounds have multiple stereocenters and also are superimposable on their mirror image.
Enantiomers are the chiral molecules that are mirror images of one another.
The reagent, potassium iodide, is a water-soluble inorganic salt.
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An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Compound W, C6H13Cl, undergoes base-promoted E2 elimination to give a single C6H₁2 alkene, Y. Compound X, C6H13Br, undergoes a similar reaction to form Y and an
isomeric alkene Z.
W is chiral; X is not.
Catalytic hydrogenation of Y and Z produces 2-methylpentane.
Propose structures for W and X.
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• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
-8)
ChemDoodleⓇ
Sn [F
(R)-2-butanol reacts with phosphorus tribromide to give A (C4H9Br). Treatment of A with sodium cyanide in DMF gives B (C5H9)N. B is optically
active. Draw the structure of B.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
Show stereochemistry in a meso compound.
Sn [F
?
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Chapter FRP Solutions
Organic Chemistry
Ch. FRP - Prob. 1PCh. FRP - 2. Which member of these pairs is the more polar?...Ch. FRP - 5. Though they each contain only one type of...Ch. FRP - Predict the products from each of the following...Ch. FRP - Prob. 5PCh. FRP - Prob. 6PCh. FRP - Prob. 7PCh. FRP - Prob. 8PCh. FRP - Predict the products from each of the following...Ch. FRP - Prob. 10P
Ch. FRP - 13. Starting with propyne and using any other...Ch. FRP - Bromination of 2-methylbutane yields predominantly...Ch. FRP - An alkane (A) with the formula C6H14 reacts with...Ch. FRP - Prob. 14PCh. FRP - Prob. 15PCh. FRP - Dehydrohalogenation of meso-1, 2-dibromo-1,...Ch. FRP - Prob. 17PCh. FRP - Prob. 18PCh. FRP - 27. (R)-3-Methyl-1-pentene is treated separately...Ch. FRP - Prob. 20PCh. FRP - Prob. 21PCh. FRP - Prob. 22PCh. FRP - Prob. 23PCh. FRP - Synthesize the following compound by a method that...Ch. FRP - Provide three methods that employ Grignard...Ch. FRP - 34. Compound Yexhibits one NMR signal at (a...Ch. FRP - Prob. 27PCh. FRP - 36. Compound X shows a strong IR absorption band...Ch. FRP - Prob. 29PCh. FRP - 38. In addition to more highly fluorinated...Ch. FRP - Fluorination of (R)-2-flurobutane yields a mixture...Ch. FRP - Prob. 32PCh. FRP - Prob. 33P
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