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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
a. Show two ways to convert an alkyl halide into an alcohol that contains one additional carbon atom. b. Show how a primary alkyl halide can be converted into an amine that contains one additional
Show how each of the following compounds could be synthesized from the given starting material:a.b. c. d.
Fill in the blank with "oxidized" or "reduced." a. Secondary alcohols are _____ to ketones. b. Acyl halides are _____ to aldehydes. c. Aldehydes are _____ to primary alcohols. d. Alkenes are _____ to
Give the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction:a.b. c. d. e. f. g. h. i. j. k. l. m. n. o. p. q. r.
How could each of the following compounds be converted toa.b. CH3CH2CH2CH2OHc. CH3CH2CH2CH2Brd. CH3CH2CH=CH2
Identify A-G:
Identify the alkene that would give each of the following products upon ozonolysis followed by treatment with hydrogen peroxide:a.b. c. d. e. f.
Fill in each box with the appropriate reagent:a.b. c.
Give the products of the following reactions:a.b. c. d. e. f.
Describe how 1-butyne can be converted into each of the following compounds:a.b.
a. Give the products obtained from ozonolysis of each of the following compounds, followed by work-up under oxidizing conditions:b. What compound would form the following products upon reaction with
Show how each of the following compounds can be prepared from cyclohexene:a.b. c. d.
The 1H NMR spectrum of the product obtained when an unknown alkene reacts with ozone and the ozonolysis product is worked up under oxidizing conditions is shown. Identify the alkene.
Chromic acid oxidizes 2-propanol six times faster than it oxidizes 2-deuterio-2-propanol. Explain.
Fill in each box with the appropriate reagent:
Show how each of the following compounds could be prepared, using the given starting material:a.b. c. d. e.
Which of the following compounds would be more rapidly cleaved by HIO4?
Can carbon-nitrogen double and triple bonds be reduced by lithium aluminum hydride? Explain your answer.
Show how cyclohexylacetylene can be converted into each of the following compounds:a.b.
Show how the following compounds could be synthesized. The only carbon-containing reagents that are available for each synthesis are shown.a.b. c.
The catalytic hydrogenation of 0.5 g of a hydrocarbon at 25 °C consumed about 200 mL of H2 under 1 atm of pressure. Reaction of the hydrocarbon with ozone, followed by treatment with hydrogen
Tom Thumbs was asked to prepare the following compounds from the given starting materials. The reagents he chose to use for each synthesis are shown.a. Which of his syntheses were successful?b. What
The catalytic hydrogenation of compound A formed compound B. The IR spectrum of compound A and the spectrum of compound B are shown. Identify the compounds.
Diane Diol worked for several days to prepare the following compounds:She labeled them carefully and went to lunch. To her horror, when she returned, she found that the labels had fallen off the
Show how propyl propionate could be prepared, using allyl alcohol as the only source of carbon.
Compound A has a molecular formula of C5H12O and is oxidized by an acidic solution of sodium dichromate to give compound B, whose molecular formula H5SO4 is When compound A is heated with C and D are
Show how you could converta. maleic acid to (2R,3S)-tartaric acidb. fumaric acid to (2R,3S)-tartaric acidc. maleic acid to (2R,3R)- and (2S,3S)-tartaric acidd. fumaric acid to (2R,3R)- and
Give the products of the following reactions (assume that excess reducing agent is used in d):a.b. c. d.
Identify A through O:
Show how the following compounds could be prepared, using only the indicated starting material as the source of carbon:a.b. c. d.
A primary alcohol can be oxidized only as far as the aldehyde stage if the alcohol is first treated with tosyl chloride (TsCl) and the resulting tosylate is allowed to react with dimethyl sulfoxide
Identify the alkene that gives each of the following products upon ozonolysis, followed by treatment with dimethyl sulfide:a.b.
Propose a mechanism to explain how dimethyl sulfoxide and oxalyl chloride react to form the dimethylchlorosulfonium ion used as the oxidizing agent in the Swern oxidation.
Show how the following compounds could be prepared, using only the indicated starting material as the source of carbon:a.b. c. d. e. f.
Terpineol (C10H18O) is an optically active compound with one asymmetric carbon. It is used as an antiseptic. Reaction of terpineol with H2/pt forms an optically inactive compound (C10H20C) Heating
Propose a mechanism for the following enzyme-catalyzed reaction. (Notice that Br is attached to the more substituted carbon.)
How could you synthesize the following compounds from starting materials containing no more than four carbons?a.b.
Give the product formed from the reaction of each of the following alcohols with a. An acidic solution of sodium dichromate: b. The reagents required for a Swern oxidation: 1. 3-pentanol 2.
Propose a mechanism for the chromic acid oxidation of 1-propanol to propanal.
Name the following compounds:a.b. c. d. e. f.
Describe a synthesis for each of the following compounds, using the given starting material and any necessary reagents:a.b.
Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?
Give the products that would be obtained by treating the following tertiary amines with hydrogen peroxide followed by heat:a.b. c. d.
Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with an excess of the carbonyl compound instead?
When pyrrole is added to a dilute solution of D2SO4 in D2O, in 2-deuteriopyrrole is formed. Propose a mechanism to account for the formation of this compound.
Use resonance contributors to explain why pyrrole is protonated on C-2 rather than on nitrogen.
Explain why pyrrole (PKa ~ 17) is less acidic than cyclopentadiene (PKa = 15) even though nitrogen is considerably more electronegative than carbon.
Will an amide be formed from the reaction of an acyl chloride with an aqueous solution of pyridine? Explain your answer.
Give the product of the following reaction:
Why is the of the conjugate acid of morpholine significantly lower than the of the conjugate acid of piperidine?
a. Propose a mechanism for the following reaction:b. What other product is formed?
Rank the following compounds in order of decreasing ease of removing a proton from a methyl group:
Give the major product of the following reaction:
List imidazole, pyrrole, and benzene in order of decreasing reactivity toward electrophilic aromatic substitution.
Imidazole boils at 257 °C, whereas N-methylimidazole boils at 199 °C. Explain this difference in boiling points
What percent of imidazole will be protonated at physiological pH (7.3)?
Is porphyrin aromatic?
Show how the last two porphobilinogen molecules are incorporated into the porphyrin ring.
Name the following compounds:a.b. c. d.
Give the product of each of the following reactions:a.b. c. d. e. f. g. h. i.
a. Draw the structure of 3-quinuclidinone.b. What is the approximate pka of its conjugate acid?c. Which has a lower PKa the conjugate acid of 3-bromoquinuclidine or the conjugate acid of
List the following compounds in order of decreasing acidity:
Which of the following compounds is easier to decarboxylate?
Rank the following compounds in order of decreasing reactivity in an electrophilic aromatic substitution reaction
One of the following compounds undergoes electrophilic aromatic substitution predominantly at C-3, and one undergoes electrophilic aromatic substitution predominantly at C-4. Which is which?
Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such asa. What are the major and minor products of the following reaction?b. Would you
A Hofmann degradation of a primary amine forms an alkene that gives butanal and 2 methylpropanal upon ozonolysis and workup under reducing conditions. Identify the amine.
The dipole moments of furan and tetrahydrofuran are in the same direction. One compound has a dipole moment of 0.70 D, and the other has a dipole moment of 1.73 D. Which is which?
Show how the vitamin niacin can be synthesized from nicotine
The chemical shifts of the C-2 hydrogen in the 1H NMR spectra of pyrrole, pyridine, and pyrrolidine are and Match each chemical shift with its heterocycle.
Explain why protonation of aniline has a dramatic effect on the compound's UV spectrum, whereas protonation of pyridine has only a small effect on that compound's UV spectrum.
Why is it that a halide ion such as Br- can react with a protonated primary alcohol, but cannot react with a protonated primary amine?
Explain why pyrrole is a much stronger acid than ammonia (pKa = 36).
Propose a mechanism for the following reaction:
Quinolines are commonly synthesized by a method known as the Skraup synthesis, which involves the reaction of aniline with glycerol under acidic conditions. Nitrobenzene is added to the reaction
Propose a mechanism for each of the following reactions:a.b.
Give the major product of each of the following reactionsa.b. c. d. e. f. g. h. i.
When piperidine undergoes the indicated series of reactions, 1,4-pentadiene is obtained as the product. When the four different methyl-substituted piperidines undergo the same series of reactions,
a. Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution b. At what position does pyridine-N-oxide undergo electrophilic
Propose a mechanism for the following reaction:
Explain why the aziridinium ion has a considerably lower (8.0) than that of a typical secondary ammonium ion (10.0). (Hint: Recall that the larger the bond angle, the greater the s character, and the
Pyrrole reacts with excess para-(N,N-dimethylamino)benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.
Give the product of each of the following reactions:a.b. c. d.
2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis. Propose a mechanism for this reaction. (Hint: The reactive species is
What starting materials are required for the synthesis of the following compounds, using the Fischer indole synthesis? (Hint: See Problem 50.)a.b. c.
Organic chemists work with tetraphenylporphyrins rather than porphyrins because tetraphenylporphyrins are much more resistant to air oxidation. Tetraphenylporphyrin can be prepared by the reaction of
Propose a mechanism different from the one shown in Section 21.11 for the biosynthesis of porphobilinogen.
What is the difference between the reaction that occurs when isopropyltrimethylammonium hydroxide is heated and the reaction that occurs when 2-bromopropane is treated with hydroxide ion?
What are the minor products in the preceding Hofmann elimination reaction?
Give the major products of each of the following reactionsa.b. c. d.
Identify the amine in each case. a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a
a. What other monosaccharide is reduced only to the alditol obtained from the reduction of1. D-talose?2. D-galactose?b. What monosaccharide is reduced to two alditols, one of which is the alditol
Write the mechanism for the base-catalyzed conversion of D-fructose into D-glucose and D-mannose.
When D-tagatose is added to a basic aqueous solution, an equilibrium mixture of three monosaccharides is obtained. What are these monosaccharides?
a. Name an aldohexose other than D-glucose that is oxidized to D-glucaric acid by nitric acid. b. What is another name for D-glucaric acid? c. Name another pair of aldohexoses that are oxidized to
Name a ketose and another aldose that form the same osazone as a. D-ribose b. D-altrose c. L-idose d. D-galactose
Identify A, B, C, and D in the preceding problem if D is oxidized to an optically inactive aldaric acid, A, B, and C are oxidized to optically active aldaric acids, and interchanging the aldehyde and
Draw Fischer projections of L-glucose and L-fructose.
4-Hydroxy- and 5-hydroxyaldehydes exist primarily in the cyclic hemiacetal form. Give the structure of the cyclic hemiacetal formed by each of the following: a. 4-hydroxybutanal b. 5-hydroxypentanal
Draw the following sugars, using Haworth projections: a. α-D-galactopyranose b. α -D-tagatopyranose c. α -L-glucopyranose
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