ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Question
Chapter 26, Problem 44P
Interpretation Introduction
Interpretation:
(a) The mechanism using curved arrows to show the flow of electrons is to be suggested for the given cyclization reaction.
(b) A stepwise mechanism is to be written for the hydrolysis of the conjugate acid of the iminolactone to corresponding lactone that cleaves the peptide chain.
Concept Introduction:
Cyanogen bromide adds to the sulfur atom of the methionine residue forming a sulfonium ion.
The sulfonium ion cyclizes to form an iminolactone.
Iminolactone undergoes hydrolysis, cleaving the bond between nitrogen and the ring carbon. This results in the peptide chain being cleaved between carbonyl of the methionine residue and the next amino acid.
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Predict the reactants used in the formation of the following compounds using Acid-Catalyzed dehydration reaction
Can I please get help with this?
.. Give the major organic product(s) for each of the following reactions or sequences of reactions. Show
ll relevant stereochemistry [3 ONLY].
A
H Br 1. NaCN
2 NaOH, H₂O, heat
3. H3O+
B.
CH₂COOH
19000
1. LiAlH4 THF, heat
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CH Br
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D.
Br
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E.
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2 H₂O+
Chapter 26 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 26.1 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Prob. 3PCh. 26.3 - Prob. 4PCh. 26.3 - Prob. 5PCh. 26.4 - Prob. 6PCh. 26.4 - Prob. 7PCh. 26.4 - Prob. 8PCh. 26.5 - Prob. 9PCh. 26.6 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.7 - Prob. 13PCh. 26.7 - Prob. 14PCh. 26.7 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Prob. 17PCh. 26.9 - Prob. 18PCh. 26.10 - Digestion of the tetrapeptide of Problem 26.18...Ch. 26.12 - Prob. 20PCh. 26.12 - Prob. 21PCh. 26.15 - Prob. 22PCh. 26.15 - Prob. 23PCh. 26.16 - Prob. 24PCh. 26.17 - Prob. 25PCh. 26.18 - Prob. 26PCh. 26 - Prob. 27PCh. 26 - Prob. 28PCh. 26 - Prob. 29PCh. 26 - Prob. 30PCh. 26 - Prob. 31PCh. 26 - Prob. 32PCh. 26 - Prob. 33PCh. 26 - Prob. 34PCh. 26 - Prob. 35PCh. 26 - Prob. 36PCh. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - Prob. 39PCh. 26 - Prob. 40PCh. 26 - If you synthesized the tripeptide Leu-Phe-Ser from...Ch. 26 - Prob. 42PCh. 26 - Prob. 43PCh. 26 - Prob. 44PCh. 26 - Prob. 45DSPCh. 26 - Prob. 46DSPCh. 26 - Prob. 47DSPCh. 26 - Prob. 48DSPCh. 26 - Prob. 49DSPCh. 26 - Prob. 50DSP
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