Organic Chemistry - Access
7th Edition
ISBN: 9780321820020
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 20, Problem 40P
Pyrrole reacts with excess para-(N,N-dimethylamino) benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.
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p-Nitrobenzaldehyde is more reactive toward nucleophilic additions than p-methoxybenzaldehyde. Explain.
The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of
formation of an enamine from a ketone,
Michael addition to an α,β-unsaturated carbonyl compound, and
hydrolysis of the enamine in dilute acid to regenerate the ketone.
Consider the Stork reaction between acetophenone and 3-buten-2-one.
Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine.
Draw the structure of the Michael addition product.
Draw the structure of the final product.
Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.
Chapter 20 Solutions
Organic Chemistry - Access
Ch. 20.1 - Name the following:Ch. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Draw the product of each of the following...Ch. 20.5 - Prob. 6PCh. 20.5 - When pyrrole is added to a dilute solution of...Ch. 20.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 20.6 - Prob. 10PCh. 20.6 - How to the mechanisms of the following reactions...Ch. 20.6 - Prob. 12P
Ch. 20.6 - Rank the following compounds from easiest to...Ch. 20.7 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.7 - Prob. 16PCh. 20.7 - Prob. 17PCh. 20.7 - Prob. 18PCh. 20.7 - Prob. 19PCh. 20.7 - Prob. 20PCh. 20 - Name the following:Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Which of the following compounds is easier to...Ch. 20 - Rank the following compounds from most reactive to...Ch. 20 - One of the following compounds undergoes...Ch. 20 - Benzene undergoes electrophilic aromatic...Ch. 20 - The dipole moments of furan and tetrahydrofuran...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - The chemical shifts of the C-2 hydrogen in the...Ch. 20 - Explain why protonating aniline has a dramatic...Ch. 20 - Prob. 33PCh. 20 - Propose a mechanism for the following reaction:Ch. 20 - Prob. 35PCh. 20 - Propose a mechanism for the following reactions:Ch. 20 - Prob. 37PCh. 20 - a. Draw resonance contributors to show why...Ch. 20 - Prob. 39PCh. 20 - Pyrrole reacts with excess...Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Organic chemists work with tetraphenylporphyrins...
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- 3′-chloro-4′-methoxyacetophenone has a higher melting point than 4-methoxyacetophenone. explain why?arrow_forwardRank the following compounds in order of increasing basicity: I. p-nitroaniline III. N-methylaniline II. p-aminobenzaldehyde IV. p-methylanilinearrow_forwardExplain this observation: Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5CH=CHCO2CH2CH3) reacts with electrophiles to afford meta- disubstituted arenes.arrow_forward
- What will be the right combination of reagents to be required for the synthesis of the following compound? a. Ethanal + n-Propylamine b. Ethanal + isopropylamine c. Propanal + Ethylamine d. Ethylamine + Ethanal .arrow_forwardwhich of the following compounds would be the most basic? A. p-methoxyaniline B. p-nitroaniline C. p-toluidine D. aniline E. All would have the same basicityarrow_forwardWhat product will be made with aqueous acid?arrow_forward
- Show how the p-bromoanisole can be synthesized from benzene:arrow_forwardWhich of the following set of reagents will make cyclobutamine from bromocyclobutane? a NaN3 / ethanol and LiAlH4 in ether solution b NH3 and NaBH4 in ethanol solution c NaCN and LiAlH4 in ether solution d NH3 and H2 /Pdarrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forward
- Arrange the compounds in order of INCREASING reactivity towards bromination. Toluene, Nitrobenzene, Anisole, Aniline Acetophenone, Bromobenzene, Aniline, Phenol Acetanilide, Benzaldehyde, Toluene, Iodobenzenearrow_forwardExplain 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_forward
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