ORG CHEM CONNECT CARD
6th Edition
ISBN: 9781264860746
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 16, Problem 53P
For each N-substituted benzene, predict whether the compound reacts faster than, slower than, or at a similar rate to benzene in electrophilic
a. b. c. d.
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Determine whether each nucleophilic acyl substitution is likely to occur.
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Explain the reactivity and orientation effects observed in each heterocycle.
a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.
b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.
Chapter 16 Solutions
ORG CHEM CONNECT CARD
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.4 - Prob. 4PCh. 16.5 - Prob. 5PCh. 16.5 - Prob. 6PCh. 16.5 - Prob. 9PCh. 16.5 - Problem 18.9 Draw the product of each reaction
a....Ch. 16.5 - Prob. 11PCh. 16.5 - Prob. 12P
Ch. 16.5 - Prob. 13PCh. 16.6 - Prob. 14PCh. 16.6 - Problem 18.14 Draw all resonance structures for...Ch. 16.6 - Problem 18.15 Classify each substituent as...Ch. 16.7 - Prob. 17PCh. 16.9 - Prob. 22PCh. 16.10 - Problem 18.20 Draw the products of each...Ch. 16.10 - Prob. 24PCh. 16.11 - Problem 18.22 Draw the products formed when each...Ch. 16.12 - Problem 18.23 Devise a synthesis of each compound...Ch. 16.13 - Problem 18.24 Draw the products of each...Ch. 16.13 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 16.13 - Problem 18.26 Draw the products of each...Ch. 16.13 - Prob. 30PCh. 16 - Prob. 37PCh. 16 - 18.35 What is the major product formed by an...Ch. 16 - 18.36 Draw the products formed when phenol is...Ch. 16 - Problem 18.37 Draw the products formed when each...Ch. 16 - 18.38 Draw the products of each reaction.
a. d....Ch. 16 - 18.39 What products are formed when benzene is...Ch. 16 - Prob. 49PCh. 16 - 18.47 For each of the following substituted...Ch. 16 - 18.48 Consider the tetracyclic aromatic compound...Ch. 16 - 18.49 For each N-substituted benzene, predict...Ch. 16 - Prob. 54PCh. 16 - 18.51 Using resonance structures, explain why a...Ch. 16 - Prob. 56PCh. 16 - 18.53 Rank the aryl halides in each group in order...Ch. 16 - Prob. 64PCh. 16 - Prob. 65PCh. 16 - Prob. 66PCh. 16 - 18.63 Synthesize each compound from benzene and...Ch. 16 - Problem 18.64 Synthesize each compound from...
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- Rank the compounds according to their increasing reactivity toward electrophilic substitution. 1. Benzaldehyde 2. o-dimethylbenzene 3. nitrobenzene 4. phenolarrow_forwardSynthesize each compound from benzene and any other organic or inorganic reagents. NH2 NO2 Br. a. е. NH2 Br CH3 Br NH2 b. d. HOOC NO2 (РАВA) sunscreen componentarrow_forwardGive detailed Solution with explanation neededarrow_forward
- Determine which ring in each compound is more reactive in electrophilic aromatic substitution, and draw the product(s) formed when each compound is treated with the general electrophile E+.arrow_forwardDraw the organic products formed in each reactionarrow_forwardEnols are quite reactive toward electrophiles than alkenes because: а. The OH group has a powerful electron-donating O resonance effect b. A resonance structure can be drawn that places a negative charge on one of the carbon atoms, making this carbon electrophilic С. The enol can react with nucleophilic carbon to form a new bond to carbon d. None of the options are correctarrow_forward
- Explain the reactivity and orientation effects observed in each heterocycle.a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.arrow_forwardCoumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.arrow_forwardDevise a synthesis of each biologically active compound from benzenearrow_forward
- Explain the steps of the electrophilic aromatic substitution of this reactionarrow_forwardRank the following compounds from most reactive to least reactive toward nucleophilic addition:arrow_forwardRank by rate of electrophilic aromatic substitution. The compound that reacts the fastest in an electrophilic aromatic substitution is 1, while the compound that reacts the slowest is 5. b. H NH2 5 3 -arrow_forward
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