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Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 18, Problem 18.3P
Interpretation Introduction
Interpretation: The mechanism for the chlorination of benzene using
Concept introduction: Benzene is an
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Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown.
Note: You do not need to draw any of the side products of the reaction, only the substitution product.
□
+
HO
1
+ X
S
Click and drag to start
drawing a structure.
Acid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The
first step is the protonation of the alcohol oxygen to form an oxonium ion.
Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures,
including hydrogen atoms, of the three organic products of this reaction.
н
н
:бн
н
Нас.
Нас.
CHз
CH3
ČH3
CH3
3-methyl-2-butanol
an oxonium ion
Major Product
Minor Product
Minor Product
Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown.
Note: You do not need to draw any of the side products of the reaction, only the substitution product.
H
× 5
Br
+
HO
+
1
Click and drag to start
drawing a structure.
Chapter 18 Solutions
Organic Chemistry-Package(Custom)
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - What acid chloride would be needed to prepare each...Ch. 18 - Prob. 18.7PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.9PCh. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Classify each substituent as electron donating or...Ch. 18 - Prob. 18.15PCh. 18 - Label each compound as more or less reactive than...Ch. 18 - Rank the following compounds in order of...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 - Prob. 18.22PCh. 18 - Devise a synthesis of each compound from the...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 - Synthesize each compound from benzene.Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - Draw the products formed when phenol (C6H5OH) is...Ch. 18 - Prob. 18.37PCh. 18 - Draw the products of each reaction. a. e. i. b. f....Ch. 18 - What products are formed when benzene is treated...Ch. 18 - Draw the products of each reaction. a.d. b.e. c.f.Ch. 18 - You have learned two ways to make an alkyl...Ch. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.45PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - Which benzene ring in each compound is more...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Explain each statement in detail using resonance...Ch. 18 - Prob. 18.50PCh. 18 - Explain why the meta product is formed in the...Ch. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - Prob. 18.53PCh. 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 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.60PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.62PCh. 18 - Prob. 18.63PCh. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from toluene (C6H5CH3)...Ch. 18 - Prob. 18.67PCh. 18 - Use the reactions in this chapter along with those...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.72PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - Prob. 18.74PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79PCh. 18 - Prob. 18.80P
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- Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. D xx + H₂O + X Click and drag to start drawing a structure.arrow_forwardDraw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. HO + C+ Cl с с + T X Ć Click and drag to start drawing a structure. Karrow_forwardx ✓5 Br 6 Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. Ö + X S 8 C 9 Click and drag to start drawing a structure. 10arrow_forward
- Why must dehydration reactions of alcohols be carried out under acid catalysis? O 1) the hydroxide group is a poor leaving group and must be protonated to 1) generate a better leaving group. 2) the hydroxide group is a great leaving group and does not need to be protonated to generate a better leaving group. O 3) the acid isn't necessary for the reaction. O4) None of these are correct answers.arrow_forwardA certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure.arrow_forward2) How might you prepare 2-phenylethanol from benzyl bromide? More than one step is needed. O 236 Sajjad Oday, 10:36 PMarrow_forward
- The reaction of ozone with 2-butene leads to -10 formation of aldehyde + ketone 0 aldehyde + alcohol 0 two molecules of carboxylic acid 0arrow_forwardWhat is the name if the reaction for the synthesis of Benzhydrol? What is the full reaction mechanism? Benzhydrol MgBr 1. ether 2. H*, H₂O OHarrow_forwardAcetals are formed from the reaction of two alcohols with a carbonyl under acidic conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol molecules. Choose the factor that explains the difference in reaction rates. A) The reaction with 1,2-ethanediol has a lower AH (enthalpy) of reaction. B) The reaction with 1,2-ethanediol has a higher AH (enthalpy) of reaction. C) The reaction with 1,2-ethanediol has a more favorable entropy of reaction.arrow_forward
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