ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Textbook Question
Chapter 27, Problem 24P
When 6-chloropurine is heated with aqueous sodium hydroxide, it is quantitatively converted to hypoxanthine. Suggest a reasonable mechanism for this reaction.
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Chapter 27 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 27.1 - Problem 27.1 Write a structural formula for the...Ch. 27.1 - Prob. 2PCh. 27.1 - Prob. 3PCh. 27.2 - Prob. 4PCh. 27.3 - Prob. 5PCh. 27.3 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.5 - Prob. 8PCh. 27.5 - Prob. 9PCh. 27.6 - Prob. 10P
Ch. 27.7 - Prob. 11PCh. 27.9 - Prob. 12PCh. 27.12 - 27.13 Modify Figure 27.12 so that it corresponds...Ch. 27.13 - Prob. 14PCh. 27 - Prob. 15PCh. 27 - Prob. 16PCh. 27 - Prob. 17PCh. 27 - Nebularine is a toxic nucleoside isolated from a...Ch. 27 - Prob. 19PCh. 27 - The 5-nucleotide of inosine, inosinic acid...Ch. 27 - Prob. 21PCh. 27 - (a) The two most acidic hydrogens of uracil have...Ch. 27 - The phosphorylation of -D-glucopyranose by ATP...Ch. 27 - When 6-chloropurine is heated with aqueous sodium...Ch. 27 - Prob. 25PCh. 27 - Prob. 26PCh. 27 - Prob. 27PCh. 27 - Prob. 28PCh. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...
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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forward
- Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forwardComplete the following transformations by providing reagents or products:arrow_forwardWhen 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw the structural formula of this lactone and propose a mechanism for its formationarrow_forward
- Provide reagents needed to bring about the following transformation.arrow_forwardProvide the reagents needed to bring about the following transformations.arrow_forwardDraw mechanisms for the acetylation of aniline, the bromination of acetanilide and the hydrolysis of 4-bromoacetanilide (REMEMBER: NBS generates bromine in solution) Reagents used: aniline, acetic acid, acetic anhydride to make acetanilide. Then acetanilide dissolved in acetic acid, NBS, aqHBr to make 4-bromoaxetanilinde. Then 4-bromoacetanilinde, EtOh, HCl and NaOH (to neutralise) to make 4-bromoaniline Please include drawings of the mechanisms as well as a written explanation as it helps me process exactly whats going on...arrow_forward
- The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific.arrow_forward2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis.Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)arrow_forwardPropose a detailed mechanism for the following reactions: a) Reaction of 3-methylbutanal and diethyl malonate in the presence of sodium ethoxide solution in ethanol. b) Reaction of diethyl hexanedioate in the presence of sodium ethoxide followed by acid work up to form a beta-ketoester.arrow_forward
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