Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 18, Problem 1LGP
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5. Consider the synthesis of 2-butanone from butyne:
Hg2+
CH3CH,-C=C–H
CH3CH, Ĉ
-CH3
H3o*
(i) Draw the structure of the compound D.
(ii) Compound D isomerizes to form 2-butanone. What is this isomeric process called?
(iii) Use the mechanism to show the conversion of compound D to 2-butanone.
Proteases are enzymes that can break covalent bonds in proteins. Proteases play major roles in the regulation of biological processes,
so compounds that inhibit their function, called protease inhibitors, have potential as therapeutic agents. While preparing several
potential protease inhibitors, compound 1 was converted into compound 3 via alkyne 2, as shown. (J. Org. Chem. 1989, 54, 3963-
3972) Draw the structure of alkyne 2, and propose reagents for converting 1 into 3.
Step 1
Br
Br
Ph
alle
Br
Br
Edit Drawing
OH
Modify the given structure of 1 to draw alkyne 2. An eraser is available, and you can use the single bond tool to add/remove pi
bonds.
OH
2
Ph
O
ell (-10)
Ph =
3
OH
Hw.198.
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - Prob. 37PCh. 18 - Prob. 38PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...
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- Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octetarrow_forwardA chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.arrow_forwardAn 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.arrow_forward
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