Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 20.6, Problem 11P
Interpretation Introduction
Interpretation:
The isoprene units has to be marked in lycopene and
Concept Introduction:
Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.
Monoterpenes are those terpenes with two isoprene units-have 10 carbons, sesquiterpenes have 15 carbons, diterpenes have 20 carbons, triterpenes have 30 carbons and tetraterpenes have 40 carbons.
Isopentenyl pyrophosphate (isoprene) is the five-carbon compound used for the biosynthesis of terpenes.
Isoprene unit:
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Compounds X and Y both have the formula C7H₁4.
Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylhexane.
The heat of hydrogenation of X is greater than that of Y.
Both X and Y react with HCI to give the same single C7H15Cl compound as the major product.
What is the structure of X?
• In cases where there is more than one answer, just draw one.
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ChemDoodleⓇ
146
Mark off the isoprene units in lycopene and beta-carotene. Can you detect a similarity in the way in which squalene, lycopene, and beta-carotene are biosynthesized?
5. An unknown hydrocarbon A with the formula C,H12 reacts with 1 molar equivalent of
H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B.
When oxidized with KMNO4 in acidic solution, A gives two fragments. One fragment
is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the
structures of A, B, and C? Write all reactions and show your reasoning.
Chapter 20 Solutions
Essential Organic Chemistry, Global Edition
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.2 - Draw the structure of an optically active fat...Ch. 20.4 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - The membrane phospholipids in deer have a higher...Ch. 20.4 - Prob. 9PCh. 20.6 - Prob. 10PCh. 20.6 - Prob. 11P
Ch. 20.6 - Prob. 12PCh. 20.7 - Propose a mechanism for the biosynthesis of...Ch. 20.7 - Prob. 14PCh. 20.8 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 20.9 - Prob. 16PCh. 20 - Prob. 17PCh. 20 - Prob. 18PCh. 20 - Cardiolipins are found in heart muscles. Draw the...Ch. 20 - Prob. 20PCh. 20 - 5-Androstene-3,17-dione is isomerized to...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Prob. 24PCh. 20 - Eudesmol is a sesquiterpene found in eucalyptus....
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- Analyze the following structure of abscisic acid in terms of isoprene units joined by head-to-tail linkages. HO. CO2H (1) How many isoprene units are there in a abscisic acid molecule? (2) Classify abscisic acid as a monoterpene (one terpene unit), a sesquiterpene (1.5 terpene units), or a diterpene (2 terpene units).arrow_forwardExplain briefly and clearly the following concepts, taking as reference the molecule of n-butane and the corresponding drawings or illustrations. See pages 149-152 of the book Organic Chemistry, sixth edition (J. G. Smith). 4. What is steric hindrance in a conformation? Then draw a picture to illustrate the concept? 5. What is the torsional stress of a conformation? Then draw a picture to illustrate the concept? 6. Describe 1,3-diaxial interaction and illustrate with a specific example.arrow_forwardCalculate the units of unsaturation of C6H7NO. And draw out the structure.arrow_forward
- For the following alkene, assign the configuration of the double bond as either Z or E. Farrow_forwardNH, CH31(excess) aq. Na2CO3 →A A48 "A".... NH, CH3 NH, CH, H,C (1) (2) CH3 CH, NH2 JA) Ph-N(CH) (3) CH, CH3arrow_forwardMark off the isoprene units in lycopene and β-carotene. Can you detect a similarity in the way in which squalene, lycopene, and β-carotene are biosynthesized?arrow_forward
- Analyze the following structure of phytol in terms of isoprene units joined by head-to-tail linkages. (1) How many isoprene units are there in a phytol molecule? (2) Classify phytol as a monoterpene (one terpene unit), a sesquiterpene (1.5 terpene units), or a diterpene (2 terpene units).arrow_forwardIn addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula C5H10F2. Draw the structures of all the isomers with the formula C5H10F2 that would be produced and label with a star all the chiral centers present in their structures.arrow_forwardDraw the structure of the terpene limonene and B-Caryophyllene and outline the isoprene units that make up these molecules. .arrow_forward
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