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 38P
Interpretation Introduction
Interpretation:
In the given conditions, the mechanism of formation of the aldol product by the rearrangement of epoxy alcohol is to be proposed.
Concept Introduction:
▸ TBSOTf stands for tert-butyldimethylsilyltriflate. It is the silylating reagent.
▸ TBSOTf is used for the protection of
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(19, 8, 2) Specify a synthetic scheme that would produce the compound shown above in the fewest steps possible. Use one of the starting materials shown together with any of the available reagents. Give the number of the starting material followed by the letters of the reagents in the order of their use, for example: 3be.
(R)-Pulegone is converted to (R)-citronellic acid by addition of HCI followed by treatment
with NaOH.
CI
1. NAOH
2. HCI
HCI
HO
(R)-Pulegone
(R)-Citronellic acid
Propose a mechanism for each step in this transformation and account for the regiose-
lectivity of HCI addition.
11. Compound A, C9H17N, is an optically inactive alkaloid, containing a tertiary amine that is
not located at the bridgehead of the structures fused bicyclic ring system. Exhaustive alkylation
of A with methyl iodide, followed by a Hofmann elimination reaction resulted in a racemic
mixture of chiral tertiary amine products B, C10H19N. Provide a structure for A and one of the
enantiomeric products B.
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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