Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 18, Problem 35P
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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b) Optical isomers can often be formed during these reactions. For products A-H
indicate how many different optical isomers you expect to form for each
from these reactions (you do not have to indicate whether they are diastereomers/enantiomers).
c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction
mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which
would probably explode when isolated. What is the structure of substance V?
*24
X
1: ozone
V
e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III -
PhSCI in diethyl ether; IV - Selectfluor in methanol.
P
M
EtOH
NA
EtONa
PhSNa
EtOH E
H+
O
TsCl
Pyridín
F-
T2, Pd/C
G4
mCPBA
H₂SO4
10 %, H₂O
1: BH3
H◄
2: H₂O₂
ill
X
Br₂
cyclohexane
HCI
A
> В
B
HBr
warmth,
benzoylperoxid
1: ozone
2: Zn, ACOH
Mg
THF
с
D
D₂O
K
I + J
NaOH
(a)Which compound/s will produce an orange precipitate upon reaction with 2,4-DNPH?
(b)Which compound/s will test positive towards Baeyer’s test?
(c)Which compound/s will produce a brick-red precipitate upon reaction with Fehling’s reagent (CuSO4, tartrate, NaOH)?
(d)Which compound/s will test positive towards the Iodoform test?
The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde toform an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)
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 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...Ch. 18 - Prob. 1QCh. 18 - Prob. 2QCh. 18 - Prob. 3QCh. 18 - Prob. 4QCh. 18 - Prob. 5Q
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