Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 9.SE, Problem 54AP
Interpretation Introduction

Interpretation:

Hydrocarbon A(C9H12) absorbs 3 equivalents of H2 in the presence of Pd/C to yield B(C9H18). A when treated with aqueous H2SO4 in the presence of Hg(II) gives two isomeric ketones C and D. A upon oxidation with KMnO4 gives a mixture of acetic acid and tricarboxylic acid E. Based on these data, structures for the compounds A-D are to be given and the reactions are to be written.

Concept introduction:

The degree of unsaturation can be calculated by comparing the molecular formula of compound given with that of its parent hydrocarbon. Both alkenes and alkynes yield alkanes by adsorbing H2 in the presence of Pd catalyst. Alkynes require two equivalents of H2 while alkenes require one equivalent of H2 to give alkanes. Internal alkynes will yield a mixture of isomeric ketones when treated with aqueous H2SO4 in the presence of mercury (II) if they are symmetrically substituted. When oxidized with KMnO4, monosubstituted carbons in both double and triple bonds get oxidized to carboxylic acids.

To give:

Based on the data given, the structures of A-D and to write the reactions.

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Chapter 9 Solutions

Organic Chemistry

Ch. 9.8 - Prob. 11PCh. 9.9 - Show the terminal alkyne and alkyl halide from...Ch. 9.9 - Beginning with acetylene and any alkyl halide...Ch. 9.SE - Name the following alkynes, and predict the...Ch. 9.SE - From what alkyne might each of the following...Ch. 9.SE - Prob. 16VCCh. 9.SE - The following cycloalkyne is too unstable to...Ch. 9.SE - Prob. 18MPCh. 9.SE - Assuming that strong acids add to alkynes in the...Ch. 9.SE - Prob. 20MPCh. 9.SE - Prob. 21MPCh. 9.SE - Prob. 22MPCh. 9.SE - Prob. 23MPCh. 9.SE - Prob. 24MPCh. 9.SE - Reaction of acetone with D3O+ yields...Ch. 9.SE - Give IUPAC names for the following compounds:Ch. 9.SE - Draw structures corresponding to the following...Ch. 9.SE - Prob. 28APCh. 9.SE - Prob. 29APCh. 9.SE - Prob. 30APCh. 9.SE - Predict the products from reaction of l-hexyne...Ch. 9.SE - Prob. 32APCh. 9.SE - Prob. 33APCh. 9.SE - Propose structures for hydrocarbons that give the...Ch. 9.SE - Identify the reagents a-c in the following scheme:Ch. 9.SE - Prob. 36APCh. 9.SE - Prob. 37APCh. 9.SE - Prob. 38APCh. 9.SE - How would you carry out the following...Ch. 9.SE - Prob. 40APCh. 9.SE - Synthesize the following compounds using 1-butyne...Ch. 9.SE - Prob. 42APCh. 9.SE - Prob. 43APCh. 9.SE - Prob. 44APCh. 9.SE - Prob. 45APCh. 9.SE - A hydrocarbon of unknown structure has the formula...Ch. 9.SE - Compound A(C9H12) absorbed 3 equivalents of H2 on...Ch. 9.SE - Hydrocarbon A has the formula C12H8. It absorbs 8...Ch. 9.SE - Occasionally, a chemist might need to invert the...Ch. 9.SE - Prob. 50APCh. 9.SE - Prob. 51APCh. 9.SE - Prob. 52APCh. 9.SE - Prob. 53APCh. 9.SE - Prob. 54APCh. 9.SE - Prob. 55APCh. 9.SE - Prob. 56APCh. 9.SE - Prob. 57AP
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