Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 13, Problem 13.12YT
Interpretation Introduction
Interpretation:
To show how 26% was obtained as the overall yield for the six-step synthesis.
Concept introduction:
In linear synthesis, the overall product yield is the product of each step yield in the sequence.
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What do you mean by kinetic product ?
OH
SYNTHESIS
1. POCI3
2. HBr, ROOR
3. Mg, ether
4. benzaldehyde
5. H3O+ workup
6. PCC
7. CH3MgBr
8. H3O+ workup
Br
T
Complete the reactions given below. (For question 2 - KOC (CH3) 3 / heat)
Chapter 13 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 13 - Prob. 13.1PCh. 13 - Prob. 13.2PCh. 13 - Prob. 13.3PCh. 13 - Prob. 13.4PCh. 13 - Prob. 13.5PCh. 13 - Prob. 13.6PCh. 13 - Prob. 13.7PCh. 13 - Prob. 13.8PCh. 13 - Prob. 13.9PCh. 13 - Prob. 13.10P
Ch. 13 - Prob. 13.11PCh. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - Prob. 13.16PCh. 13 - Prob. 13.17PCh. 13 - Prob. 13.18PCh. 13 - Prob. 13.19PCh. 13 - Prob. 13.20PCh. 13 - Prob. 13.21PCh. 13 - Prob. 13.22PCh. 13 - Prob. 13.23PCh. 13 - Prob. 13.24PCh. 13 - Prob. 13.25PCh. 13 - Prob. 13.26PCh. 13 - Prob. 13.27PCh. 13 - Prob. 13.28PCh. 13 - Prob. 13.29PCh. 13 - Prob. 13.30PCh. 13 - Prob. 13.31PCh. 13 - Prob. 13.32PCh. 13 - Prob. 13.33PCh. 13 - Prob. 13.34PCh. 13 - Prob. 13.35PCh. 13 - Prob. 13.36PCh. 13 - Prob. 13.37PCh. 13 - Prob. 13.38PCh. 13 - Prob. 13.39PCh. 13 - Prob. 13.40PCh. 13 - Prob. 13.41PCh. 13 - Prob. 13.42PCh. 13 - Prob. 13.43PCh. 13 - Prob. 13.44PCh. 13 - Prob. 13.45PCh. 13 - Prob. 13.46PCh. 13 - Prob. 13.47PCh. 13 - Prob. 13.48PCh. 13 - Prob. 13.49PCh. 13 - Prob. 13.50PCh. 13 - Prob. 13.51PCh. 13 - Prob. 13.1YTCh. 13 - Prob. 13.2YTCh. 13 - Prob. 13.3YTCh. 13 - Prob. 13.4YTCh. 13 - Prob. 13.5YTCh. 13 - Prob. 13.6YTCh. 13 - Prob. 13.7YTCh. 13 - Prob. 13.8YTCh. 13 - Prob. 13.9YTCh. 13 - Prob. 13.10YTCh. 13 - Prob. 13.11YTCh. 13 - Prob. 13.12YT
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- Prepare benzonitrile from benzene more than one step is requiredarrow_forwardWrite the reaction mechanism for the synthesis of methyl orange.arrow_forwardCH3 CH3 H3C N. H Tetracaine Tetracaine can be synthesized from benzene. The synthesis involves the following steps: 1. Benzene + CH3CI, AICI3 to form product A; 2. A + HNO3, H2SO4 to form product B; 3. B + KMNO4, H2O to form product C; 4. C + SOCI, to form product D; 5. D + HOCH2CH2N(CH3)2 to form product E; 6. E + H2, Pt to form product F; 7. F + CH3CH2CH2CHO to form product G; 8. G + NABH3CN to form Tetracaine. Draw the structures of product A and product G. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Show the order of synthesis by drawing a reaction arrow between A and G, pointing toward the later-synthesized product.arrow_forward
- 4) Give an example of an enol which would tautomerize into a) an aldehyde and b) a ketone.arrow_forwardComplete the reactions given below.arrow_forwardUpon completion of a chemical reaction, you find you have a mixture of benzoic acid and ethyl benzoate. Propose a procedure to separate the ethyl benzoate from the mixture. You should look up the structures of benzoic acid and ethyl benzoate.arrow_forward
- Please don't provide handwritten solution....arrow_forwardWhat is the slow, rate-determining step, in the acid-catalyzed dehydration of 2- butanol? Loss of a b-hydrogen from the carbocation to form an alkene. Protonation of the alcohol to form an oxonium ion. Loss of water from the oxonium ion to form a carbocation. The simultaneous loss of a B-hydrogen and water from the oxonium ion.arrow_forwardCyclopropane decomposes fairly rapidly at moderate temperatures whereas cyclohexane is quite stable. Why is this the case?arrow_forward
- Reagents a. CeHsCHO b. NaOH, ethanol c. Pyrrolidine, cat. H* j. Brz, H* d. H2C=CHCN e. H3O* f. h. BRCH2CH=CH2 i. Na* OEt, ethanol k. K* t-Buo I. CH2(CO,Et)2 m. heat CH2CH2CN LDA g. ELOC(=0)COEt Select reagents from the table to synthesize this compound from cyclopentanone. Enter the letters of the chosen reagents, in the order that you wish to use them, without spaces or punctuation (i.e. geda).arrow_forwardShow how to convert the given starting material into the desired product. Note that some syntheses require only one step, whereas others require two or more.arrow_forwardNonearrow_forward
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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY