Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 19, Problem 28P
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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Dibenzalpropanone is a compound that can absorb UV rays and can be used as a sunscreen. Write down the reagents used to synthesize the compound dibenzalpropanone.
From each pair of compounds, choose the one with the indicated
property and explain your choice.
a) is racemized when placed in basic solution: (R)-4-methyl-2-hexanone or
(R)-3-methyl-2-hexanone
b)
forms an enamine when treated with a ketone: diethylmethylamine or
diethylamine
complete the reaction and draw:
N-methylethanamine is treated with acetophenone and the resulting product is dehydrated
Chapter 19 Solutions
Organic Chemistry (8th Edition)
Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3PCh. 19.2 - Prob. 4PCh. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6PCh. 19.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 19.5 - When pyrrole is added to a dilute solution of...Ch. 19.6 - Prob. 10PCh. 19.6 - How to the mechanisms of the following reactions...Ch. 19.6 - Prob. 12P
Ch. 19.6 - Rank the following compounds from easiest to...Ch. 19.7 - Prob. 14PCh. 19.7 - Prob. 15PCh. 19.7 - Prob. 16PCh. 19.7 - Prob. 17PCh. 19.7 - Prob. 18PCh. 19.7 - Prob. 19PCh. 19.7 - Prob. 20PCh. 19 - Name the following:Ch. 19 - Prob. 22PCh. 19 - Rank the following compounds from strongest acid...Ch. 19 - Which of the following compounds is easier to...Ch. 19 - Rank the following compounds from most reactive to...Ch. 19 - One of the following compounds undergoes...Ch. 19 - Benzene undergoes electrophilic aromatic...Ch. 19 - Pyrrole reacts with excess...Ch. 19 - The dipole moments of furan and tetrahydrofuran...Ch. 19 - Name the following:Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - a. Draw resonance contributors to show why...Ch. 19 - The chemical shifts of the C-2 hydrogen in the...Ch. 19 - Explain why protonating aniline has a dramatic...Ch. 19 - Prob. 36PCh. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38PCh. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...
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- Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.arrow_forwardThe following compounds are named incorrectly. Draw the structure of each compound and give it a correct name (either IUPAC or common is acceptable.) a) N-phenyl-N-ethyl-2-propanamine b) N-sec-butyl-N-propylmethanamine c) N-methyl-N-ethyl-4-ethylpentanamide d) 2,5-diethylhexanoic acid f Googlo Chegg Course Hero orarrow_forwardDraw the products formed when each compound is treated with HNO3 and H2SO4.State whether the reaction occurs faster or slower than a similar reaction with benzene.arrow_forward
- Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution. CH3CH2CO2H, (CH3CH2CO)2O, CH3CH2CONHCH3arrow_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_forward1) Draw AND name the product that would result upon treatment of R-3-methylheptanal with Excess aqueous sodium hydroxide together with excess chlorine. 2) Draw AND name the product that would result upon treatment of R-3-methylheptanal with Bromine in acetic acid. 3) Draw the product that would result upon treatment of R-3-methylheptanal with1-butanamine using a Dean Stark trap. Draw the product and then react the product with lithium aluminum hydride followed by hydrochloric acid. Give a complete mechanism. 4) Draw the product that would result upon treatment of R-3-methylheptanal with Disopropyl amine using a Dean Stark trap. Draw the product and then react the product with hydrogen gas in the presence of a platinum catalyst.arrow_forward
- Which of the following reactions provides iso-propyl methyl ether in a high yield? A) potassium iso-propoxide + iodomethane B) sodium methoxide + iso-propyl bromide C) methanol + iso-propyl alcohol in the presence of KOH D) iodomethane + iso-propyl bromide in the presence of KOHarrow_forwardDraw the structure (including stereochemistry) of the cyclic hemiacetal(s) formed when each hydroxy carbonyl compound is treated with aqueous acid.arrow_forwardWhat compound is formed when methyloxirane (shown below) is reacted with ethylmagnesium bromide followed by treatment with aqueous acid? 2-methyl-1-butanol 2-methyl-2-butanol 2-pentanol 3-methyl-1-butanol 1-pentanolarrow_forward
- Provide a two step method to distinguish between the following compounds. (Propanal, butanal, butanone, propanone). Explain your choice of reagents and your expected results.arrow_forwardDraw the major organic product formed when the benzoyl chloride undergoes a reaction with sodium acetate (sodium ethanoate).arrow_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 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.arrow_forward
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