Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 9.SE, Problem 53AP
Interpretation Introduction

Interpretation:

Erythrogenic acid, C18H26O2, an acetylenic fatty acid turns vivid red on exposure to light. It absorbs 5 equivalents of H2 in the presence of Pd to give stearic acid, CH3(CH2)16COOH.Upon ozonolysis it gives formaldehyde, CH2O; oxalic acid, HOOCCOOH; azelaic acid, HOOC(CH2)7COOH; and an aldehydic acid OHC(CH2)4COOH. From these data, two possible structures for Erythrogenic acid are to be given. A way to distinguish these two structures is also to be given.

Concept introduction:

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. Upon ozonolysis a monosubstituted carbon in double bond gives an aldehyde, a carbon in terminal double bond gives formaldehyde and carbons in triple bond yield carboxylic acids as products.

To give:

Two possible structures for erythrogenic acid from the data provided and a way to distinguish these two structures given.

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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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