Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 22.SE, Problem 35MP
Amino acids can also be prepared by a two-step sequence that involves Hell–Volhard–Zelinskii reaction of a
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Comparing Hydration Products Using Two Different Methods Draw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.
NaH
HO
HO
PBR3
A
(a) Name the functional groups in compounds A and B, including, if relevant, whether they are
primary (1°), secondary (2°) or tertiary (3').
(b) Propose a reagent that could be used to convert A into B.
(c) Draw the structure of the intermediate C formed by reaction of compound A with NaH.
(d) Propose the structure of the organic compound D formed by reaction with PB.3.
(e) Could HBr be used for the conversion of A into D? Explain very briefly.
17. A
(A)-aq NaOH
(B)-
K₂Cr₂O, H
[0]
→ Propanone.
i) Identify the compounds (A) and (B).
ii) Starting from compound (A), how would you obtain 2,3-dimethylbutane?
Convert compound (B) into propene.
✓ Predict
(iv) Predict the product, when compound (A) is heated with sodium
methoxide.
[2+1+1+1]
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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