ORGANIC CHEMISTRY-MOLYMOD PACKAGE
5th Edition
ISBN: 9781260227307
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 18, Problem 18.64P
Synthesize each compound from toluene
a. 
b. 
c. 
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Synthesize each compound from benzene, organic halides with < 5 C's, and any other organic or inorganic reagents.
Devise a synthesis of each substituted cyclopropane. Use acetylene (HC=CH) as a starting material in part (a) and cyclohexanone as a starting material in part (b). You may use any other organic compounds and any needed reagents.
(a) Give an acceptable name for each compound, (b) Draw the organic products formed when A or B is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.
Chapter 18 Solutions
ORGANIC CHEMISTRY-MOLYMOD PACKAGE
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - Prob. 18.6PCh. 18 - Prob. 18.7PCh. 18 - Prob. 18.8PCh. 18 - Problem 18.9 Draw the product of each reaction
a....Ch. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Problem 18.15 Classify each substituent as...Ch. 18 - Prob. 18.16PCh. 18 - Problem 18.17 Label each compound as more or less...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Problem 18.22 Draw the products formed when each...Ch. 18 - Problem 18.23 Devise a synthesis of each compound...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Problem 18.33 Synthesize each compound from...Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - 18.36 Draw the products formed when phenol is...Ch. 18 - Problem 18.37 Draw the products formed when each...Ch. 18 - 18.38 Draw the products of each reaction.
a. d....Ch. 18 - 18.39 What products are formed when benzene is...Ch. 18 - 18.40 Draw the products of each reaction.
c.
d....Ch. 18 - 18.41 You have learned two ways to make an alkyl...Ch. 18 - 18.42 Draw the structure of A, an intermediate in...Ch. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.46PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - 18.48 Consider the tetracyclic aromatic compound...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Prob. 18.50PCh. 18 - 18.51 Using resonance structures, explain why a...Ch. 18 - Prob. 18.52PCh. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - 18.63 Synthesize each compound from benzene and...Ch. 18 - Problem 18.64 Synthesize each compound from...Ch. 18 - Prob. 18.65PCh. 18 - Prob. 18.66PCh. 18 - Prob. 18.67PCh. 18 - Prob. 18.68PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.70PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - 18.72 Reaction of p-cresol with two equivalents of...Ch. 18 - Prob. 18.73PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.76PCh. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79P
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- Devise a synthesis of each compound from phenol (C6H5OH) and any other organic or inorganic reagents.arrow_forward(a) Give an acceptable name for compound A. (b) Draw the organic products formed when A is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forwardDevise a synthesis of each acetal from 1-bromo-2-methylhexane, alcohols (and diols) containing one or two carbons, and any needed inorganic reagents.arrow_forward
- Dimethyl cyclopropanes can be prepared by the reaction of an α,β-unsaturated carbonyl compound X with two equivalents of a Wittig reagent Y. Draw a stepwise mechanism for this reaction.arrow_forwardDimethyl cyclopropanes can be prepared by the reaction of an α, β- unsaturated carbonyl compound X with two equivalents of a Wittig reagent Y. Draw a stepwise mechanism for this reaction.arrow_forwardDraw a stepwise mechanism for the following reaction that forms ether D. D can be converted to the antidepressant uoxetine (trade name Prozac) in a single step.arrow_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