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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
Compound A has the formula C8H8. It reacts rapidly with KMnO4 to give CO2 and a carboxylic acid, B (C7H6O2), but reacts with only 1 molar equivalent of H2 on catalytic hydrogenation over a palladium
Plexiglas, a clear plastic used to make many molded articles, is made by polymerization of methyl methacrylate. Draw a representative segment of Plexiglas.
Poly (vinyl pyrrolidone), prepared from N-vinylpyrrolldone, is used both in cosmetics and as a synthetic blood substitute. Draw a representative segment of the polymer.
Reaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst yields methyl tert-butyl ether, CH3OC (CH3)3, by a mechanism analogous to that of acid-catalyzed alkene hydration. Write the
Isolated from marine algae, prelaureatin is thought to be biosynthesized from laurediol by the following route. Propose amechanism.
How would you distinguish between the following pairs of compounds using simple chemical tests? Tell what you would do and what you would see.(a) Cyclopentane and cyclopentane(b) 2-Hexene and benzene
Dichiorocarbene can be generated by heating sodium trichioroacetate. Propose a mechanism for the reaction, and use curved arrows to indicate the movement of electrons in each step. What relationship
(a) How many degrees of unsaturation does a-terpinene have? (b) How many double bonds and how many rings does it have? (c) Propose a structure fora-terpinene.
Evidence that cleavage of 1, 2-diols by HIO4 occurs through a five-membered cyclic periodate intermediate is based on kinetic data?the measurement of reaction rates. When diols A and B were prepared
Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis- and trans-1-bromo-3-methylcyclohexane and cis- and trans-1-bromo- 2-methylcyclohexane. The analogous reaction of HBr
Reaction of cyclohexane with mercury (II) acetate in CH3OH rather than H2O, followed by treatment with NaBH4, yields cyclohexyl methyl ether rather than Cyclohexanol Suggest a mechanism.
Use your general knowledge of alkene chemistry to suggest a mechanism for the following reaction:
Treatment of 4-penten-l-ol with aqueous Br2 yields a cyclic bromo ether rather than the expected bromohydrin. Suggest a mechanism, using curved arrows to show electronmovement.
Hydroboration of 2-mnethyl-2-pentene at 25?C followed by oxidation with alkaline 11202 yields 2-methyl-3-pentanol, but hydroboration at 160?C followed by oxidation yields 4-methyl?1?pentanol. Suggest
We?ll see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?
Hydroxylation of cis-2-butene with OsO4 yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference
Give IUPAC names for the followingsubstances:
Draw structures corresponding to the following names:(a) Phenyl benzoate(b) N-Ethyl-N-methylbutanamide(c) 2, 4-Dimethylpentanoyl chloride(d) Methyl 1-methylcyclohexanecarboxylate(e) Ethyl
Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in eachstep:
Rank the compounds in each of the following sets in order of their expected reactivity toward nucleophilic acylsubstitution:
Predict the products of the following nucleophilic acyl substitutionreactions:
The following structure represents tetrahedral alkoxide ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting
How might you prepare the following esters from the correspondingacids?
If the following molecules is treated with acid catalyst, an intra molecular esterification reaction occurs. What is the structure of the produced? (Intra molecular means within the samemolecule?
How might you prepare the following esters using a nucleophilic acyl substitution reaction of an acid chloride?(a) CH3CH2CO2CH3(b) CH3CHO2CH2CH3(c) Ethyl benzoate
Which method would you choose if you wanted to prepare cyclohexyl benzoate-Fischer esterification or reaction of an acid chloride with an alcohol? Explain.
Write the mechanism of the reaction just shown between 3, 4, 5-trimethoxybenzoyl chloride and morpholine to form trimetozine. Use curved arrows to show the electron flow in each step.
How could you prepare the following amides using an acid chloride and an amine or ammonia?(a) CH3CH2CONHCH3(b) N, N-Diethylbenzamide(c) Propanamide
How could you prepare the following ketones by reaction of an acid chloride with a lithium diorganocopper reagent?
Write the mechanism of the reaction between p-hydroxyaniline and acetic anhydride to prepare acetaminophen.
What product would you expect from reaction of 1 equivalent of methanol with a cyclic anhydride, such as phthalic anhydride (1, 2-benzenedicarboxylic anhydride)? What is the fate of the second ?half?
Why is the saponification of an ester irreversible? In other words, why doesn’t treatment of a carboxylic acid with an alkoxide ion yield an ester?
What product would you expect from the reaction of butyrolactone with LiAlH4 with DIBAH?
Show the products you would obtain by reduction of the following esters withLiAlH4:
What ester an what Grignard reagent might you start with to prepare the following alcohols?
How would you convert N-ethylbenzamide to each of the following products?(a) Benzoic acid(b) Benzyl alcohol(c) C6H5CH2NHCH2CH3
How would you use the reaction of an amide with LiAlH4 as the key step is going from bromo cyclohexane to (N, N-dimethylaminomethyl) cyclohexane? Write all the steps in the reactionsequence.
Write the mechanism of the reaction shown in figure between coenzyme A and acetyl adenylate to give acetylCoA.
Draw structures of the step-growth polymers you would expect to obtain from the followingreactions:
Kevlar, a nylon polymer prepared by reaction of 1, 4-benzenedicarboxylic acid (Terephthalic acid) with 1, 4-benzenediamine (p-phenylendiamine), is so strong that it’s used to make bulletproof
Draw the structure of the polymer you would expect to obtain from reaction of dimethyl terephthalate with a triol such as glycerol. What structural feature would this new polymer have that was not
What kinds of functional groups might compounds have if they show the following IR absorptions?(a) Absorption at 1735cm–1(b) Absorption at 1810cm–1(c) Absorptions at 2500-3300cm–1 and 1710
Propose structures for compounds that have the following formulas and IR absorptions:(a) C6H12O2, 1735 cm–1(b) C4H9NO, 1650 cm–1(c) C4H5ClO, 1780 cm–1
Name the following compounds:
How would you prepare the following compounds starting with an appropriate carboxylic acid and any other reagents needed? (Reddish brown =Br.)
The following structure represents a tetrahedral alkoxide-ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the
Electrostatic potential maps of a typical amide (acetamide) and an acyl azide (acetyl azide) are shown. Which of the two do you think is more reactive in nucleophilic acyl substitution reactions?
Give IUPAC names for the following compounds:
Draw structures corresponding to the following names:(a) p-Bromophenylacetamide(b) m-Benzoylbenzamide(c) 2, 2-Dimcthylhcxanamidc(d) Cyclohexyl cyclohexanecarboxylale(e) Ethyl 2-cyclobutenecarboxyl
Draw and name compounds that meet the following descriptions:(a) Three add chlorides having the formula C6H9CIO(b) Three amides having the formula C7H11NO
How might you prepare the following compounds from butanoic acid?(a) 1-Bulanol(b) Butanal(c) 1-Bromobutane(d) Pentanenitrile(e) 1-Butene(f) N-Methylpentanamidc(g) 2-Hexanone(h) Butyl benzene(i)
Predict the product(s) of the following reactions:
Predict the product, if any, of reaction between propanoyl chloride and the following reagents:(a) Li (Ph)2 Cu in ether (b) LiA1H4, then H3O+(c) CH3MgBr, then H3O+(d) H3O+(e)
Answer Problem2 .37 for reaction of the listed reagents with methyl propanoate.
Answer Problem 21.37 (or reaction of the listed reagents with Propanamide.
What product would you expect to obtain from Grignard reaction of an excess of phenyl magnesium bromide with dimethyl carbonate, CH3OCO2CH3?
Treatment of 5-aminopentanoic add with DCC (dicyclohexylcarbodiimide)) yields a lactam. Show the structure of the product and the mechanism of the reaction.
Outline methods for the preparation of acetophenone (phenyl methyl ketone) starting from the following:(a) Benzene(b) Bromobenzene(c) Methyl benzoate(d) Benzonitrile(e) Styrene
The following reactivity order has been found for the basic hydrolysis of p-substituted methyl benzoates: Y = NO2 > Br > H > CH3 > OCH3. How can you explain this reactivity order? Where
The following reactivity order has been found for the saponification of alkyl acetates by aqueous NaOH. Explain.CH3CO2CH3 > CH3CO2CH2CH3 > CH3CO2CH (CH3)2 > CH3CO2C (CH3)3
Explain the observation that attempted Fischer esterification of 2, 4, 6-tri-methylhenzoic acid with methanol and HC1 is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What
Fats arc biosynthesized from glycerol 3-phosphate and fatty-acyl CoA?s by a reaction sequence that begins with the following step. Show the mechanism of the reaction.
When a carboxylic acid is dissolved in isotopically labeled water, the label rapidly becomes incorporated into both oxygen atoms of the carboxylic acid. Explain.
When ethyl benzoate is heated in methanol containing a small amount of HC1, methyl benzoate is formed. Propose a mechanism for the reaction.
Tert-Butoxycarbonyl azide, a reagent used in protein synthesis, is prepared by treating tert-Butoxycarbonyl chloride with sodium azide. Propose a mechanism for thisreaction.
We said in Section 21.6 that mechanistic studies on ester hydrolysis have been carried out using ethyl propanoate labeled with 180 in the ether- like oxygen. Assume that 180-labcled acetic acid is
Treatment of a carboxylic acid with trifluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with alcohol to give an ester. (a) Propose a mechanism for formation of the
Treatment of an ?-amino acid with DCC yields a 2, 5-diketopiperazine. Propose a mechanism.
Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at 200 ?C. Propose a mechanism for this reaction. Why do you suppose such a high reaction temperature is
Butacetin is an analgesic (pain, killing) agent that is synthesized commercially from p-fluoronitrobenzene. Propose asynthesis.
Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthesis of this compound starting from 4-nitrosalicylicacid.
N, N-Diethyl-m-toluamide (DEFT) is the active ingredient in many insect- repellent preparations. Flow might you synthesize this substance fromm-bromotoluene?
Tranexamic acid, a drug useful against blood clotting, Is prepared commercially from p-methyl Benzonitrile. Formulate the steps likely to be used in the synthesis. (Don?t worry about cis-trans
One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (1) Protonation of diazomethane by the carboxylic
The hydrolysis of a biological thioester to the corresponding carboxylate is often more complex than the overall result might suggest. The conversion of succinyl CoA to succinate in the citric add
One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehydes 3-phosphate. The process occurs by phosphorylation with
Penicillin’s and other fl-lactam antibiotics (see the Focus On in this chapter) typically develop a resistance to bacteria due to bacterial synthesis of β-lactamase enzymes. Tazobactam, however,
The following reaction, called the benzilic acid rearrangement, takes place by typical carbonyl-group reactions. Propose a mechanism (Ph =phenyl).
The step-growth polymer nylon 6 is prepared from caprolactam. The reaction involves initial reaction of caprolactam with water to give an intermediate open?chain amino acid, followed by healing to
Qiana, a polyamide fiber with a silky texture, has the following structure. What is the monomer units used in the synthesis ofQiana?
What is the structure of the polymer produced by treatment of ?-propiolactone with a small amount of hydroxide ion?
Polyimides having the structure shown arc used as coatings on glass and plastics to improve scratch resistance how would you synthesize a polyimide?
How would you distinguish spectroscopically between the following isomer pairs? Tell what differences you would expect to see.(a) N-Methylpropanamide and N, N-dimethylacet amide(b)
Propose a structure for a compound, C4H7ClO2 that has the following 1R and 1H NMRspectra:
Assign structures to compounds with the following 1H NMR spectra:? (a) C4H7ClO? ??IR: 1810 cm?1? (b) C5H7NO2? ?IR: 2250, 1735 cm?1? (c) C5H10O2? ? ?IR: 1735 cm?1?
Propose structures for compounds with the following 1H NMR spectra: (a) C5H9ClO2? ?IR: 1735 cm?1? (b) C7H12O4? ? ?IR: 1735 cm?1? (c) C11H12O2? ??IR: 1710 cm?1?
Epoxy adhesives are prepared in two steps. SN2 reaction of the disodium salt of bisphenol A with epichiorohydrin forms a ?prepolymer,? which is then ?cured? by treatment with a triamine such as
In the iodoform reaction, a triiodomethyl ketone reacts with aqueous NaOH to yield a carboxylate ion and iodoform (triiodomethane). Propose a mechanism for thisreaction.
Draw structures for the enol tautomers of the following compounds:(a) Cyclopentanone(b) Methyl thioacetate(c) Ethyl acetate(d) Propanal(e) Acetic acid(f) Phenyl acetone
How many acidic hydrogen’s does each of the molecules listed in Problem 22.1 have? Identify them.Problem 22.1Draw structures for the enol tautomers of the following compounds:(a) Cyclopentanone(b)
Draw structure for all monoenol forms of the following molecule. Which would you expect to be most stable? Explain.
Write the complete mechanism of the deuteration of acetone on treatment with D3O+
Show how you might prepare 1-penten-3-one from 3-pentanone.
If methanol rather than water is added at the end of a Hell-Volhard-Zelinskii reaction, an ester rather than an acid is produced. Show how you could carry out the following transformation, and
Identify the most acidic hydrogen’s in each of the following molecules:(a) CH3CH2CHO(b) (CH3) CH3CCOCH3(c) CH3CO2H(d) Benz amide(e) CH3CH2CH2CN(f) CH3CON (CH3)2
Draw a resonance structure of the acetonitrile anion, –:CH2C ≡ N, and account for the acidity of nitriles.
Why do you suppose ketone halogenations in acidic media referred to as being acid-catalyzed, whereas halogenations in basic media are base-promoted? In other words, why is a full equivalent of base
How could you use a malonic ester synthesis to prepare the following compounds? Show allsteps.
Monoalkylated and dialkylated acetic acids can be prepared by the malonic ester synthesis, but trialkylated acetic acids (R3CCO2H) can’t be prepared. Explain
How could you use a malonic ester synthesis to prepare the following compound?
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