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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

When compound C, which is often used to model a more frequently occurring unit in lignins, was ozonized, product D was obtained. In a variety of ways it has been established that the stereochemistry
Explain how the percentages just given show that the methyl group exerts an ortho-para directive effect by considering the percentages that would be obtained if the methyl group had no effect on the
Predict the major products formed when: (a) Toluene is sulfonated. (b) Benzoic acid is nitrated. (c) Nitrobenzene is brominated. (d) Isopropylbenzene reacts with acetyl chloride and AlCl3. If the
Use resonance theory to explain why the hydroxyl group of phenol is an activating group and an ortho-para director. Illustrate your explanation by showing the arenium ions formed when phenol reacts
Phenol reacts with acetic anhydride in the presence of sodium acetate to produce the ester phenyl acetate:The CH3COOi- group of phenyl acetate, like the -OH group of phenol (Practice Problem 15.8),
(a) Give IUPAC substitutive names for the seven isomeric aldehydes and ketones with the formula C5H10O. (b) Give structures and names (common or IUPAC substitutive names) for all the aldehydes and
Write a detailed mechanism for the formation of an acetal from benzaldehyde and methanol in the presence of an acid catalyst.
Outline all steps in the mechanism for the formation of a cyclic acetal from acetone and ethylene glycol (1,2-ethanediol) in the presence of gaseous HCl.
What product would be obtained if A were treated with lithium aluminum hydride without first converting it to a cyclic acetal?
(a) Show how you might use a cyclic acetal in carrying out the following transformation:(b) Why would a direct addition of methylmagnesium bromide to A fail to give B?
Dihydropyran reacts readily with an alcohol in the presence of a trace of anhydrous HCl or H2SO4 to form a tetrahydropyranyl (THP) ether:(a) Write a plausible mechanism for this reaction. (b)
Show how you might use thioacetal formation and Raney nickel desulfurization to convert: (a) cyclohexanone to cyclohexane and (b) benzaldehyde to toluene.
(a) Show how you might prepare lactic acid from acetaldehyde through a cyanohydrin intermediate.(b) What stereoisomeric form of lactic acid would you expect to obtain?
In addition to triphenylphosphine, assume that you have available as starting materials any necessary aldehydes, ketones, and organic halides. Show how you might synthesize each of the following
Triphenylphosphine can be used to convert epoxides to alkenes-for example,Propose a likely mechanism for this reaction.
When benzaldehyde reacts with a peroxy acid, the product is benzoic acid. The mechanism for this reaction is analogous to the one just given for the oxidation of acetophenone, and the outcome
Which compound in each of the following pairs has the higher boiling point? (Answer this problem without consulting tables.) (a) Pentanal or 1-pentanol (b) 2-Pentanone or 2-pentanol (c) Pentane or
Give the structure of the product that would result from a Baeyer-Villiger oxidation of cyclopentanone.
Give a structural formula and another acceptable name for each of the following compounds: (a) Formaldehyde (b) Acetaldehyde (c) Phenylacetaldehyde (d) Acetone (e) Ethyl methyl ketone (f)
Write structural formulas for the products formed when propanal reacts with each of the following reagents:(a) NaBH4 in aqueous NaOH(b) C6H5MgBr, then H3O+(c) LiAlH4, then H2O(d) Ag2O, HO-(e)(f) H2
Give structural formulas for the products formed (if any) from the reaction of acetone with each reagent?
What products would be obtained when acetophenone reacts under each of the following conditions?(a) (b) (c) (d) (e) (f) (g)
Predict the major organic product from each of the following reactions.(a)(b) (c) (d) (e) (f) (g)
Predict the major product from each of the following reactions.(a)(b) (c) (d) (e) (f) (g) (h) (i)
Predict the major product from each of the following reactions.(a)(b) (c) (d) (e)
Provide the reagents needed to accomplish each of the following transformations.(a)(b) (c) (d) (e) (f) (g) (h)
Show how you would synthesize propanal from each of the following: (a) 1-propanol and (b) propanoic acid (CH3CH2CO2H).
Write detailed mechanisms for each of the following reactions.(a)(b) (c) (d)
Provide the reagents necessary for the following synthesis.
(a) Synthesize phenyl propyl ketone from benzene and any other needed reagents. (b) Give two methods for transforming phenyl propyl ketone into butylbenzene.
Show how you would convert benzaldehyde into each of the following. You may use any other needed reagents, and more than one step may be required. (a) Benzyl alcohol (b) Benzoic acid (c) Benzoyl
Show how ethyl phenyl ketone (C6H5COCH2CH3) could be synthesized from each of the following: (a) Benzene (b) Benzonitrile, C6H5CN (c) Benzaldehyde
Show how benzaldehyde could be synthesized from each of the following: (a) Benzyl alcohol (b) Benzoic acid (c) Phenylethyne (d) Phenylethene (styrene) (e) C6H5CO2CH3 (f) C6H5C(N
Give structures for compounds A-E.
Warming piperonal (Section 16.3) with dilute aqueous HCl converts it to a compound with the formula C7H6O3. What is this compound, and what type of reaction is involved?
Starting with benzyl bromide, show how you would synthesize each of the following:(a)(b) (c) (d)
Compounds A and D do not give positive Tollens' tests; however, compound C does. Give structures for A-D.
Provide the reagents and indicated intermediates in each of the following syntheses.(a)(b) (c) (d) (e) (f)
Dianeackerone is a volatile natural product isolated from secretory glands of the adult African dwarf crocodile. The compound is believed to be a pheromone associated with nesting and mating.
Outlined here is a synthesis of glyceraldehyde (Section 5.15A). What are the intermediates A-C and what stereoisomeric form of glyceraldehyde would you expect to obtain?
Consider the reduction of (R)-3-phenyl-2-pentanone by sodium borohydride. After the reduction is complete, the mixture is separated by chromatography into two fractions. These fractions contain
The structure of the sex pheromone (attractant) of the female tsetse fly has been confirmed by the following synthesis. Compound C appears to be identical to the natural pheromone in all respects
Provide reagents that would accomplish each of the following syntheses. Begin by writing a retrosynthetic analysis.(a)(b)
Write a detailed mechanism for the following reaction.
When(semicarbazide) reacts with a ketone (or an aldehyde) to form a derivative known as a semicarbazone, only one nitrogen atom of semicarbazide acts as a nucleophile and attacks the carbonyl carbon
Dutch elm disease is caused by a fungus transmitted to elm trees by the elm bark beetle. The female beetle, when she has located an attractive elm tree, releases several pheromones, including
The following structure is an intermediate in a synthesis of prostaglandins F2a and E2 by E. J. Corey (Harvard University). A Horner-Wadsworth-Emmons reaction was used to form the (E)-alkene. Write
Compounds W and X are isomers; they have the molecular formula C9H8O. The IR spectrum of each compound shows a strong absorption band near 1715 cm-1. Oxidation of either compound with hot, basic
The reaction of an aldehyde or ketone with a Grignard reagent is a nucleophilic addition to the carbon-oxygen double bond. (a) What is the nucleophile? (b) The magnesium portion of the Grignard
Compounds Y and Z are isomers with the molecular formula C10H12O. The IR spectrum of each compound shows a strong absorption band near 1710 cm-1. The 1H NMR spectra of Y and Z are given in Figs. 16.4
Compound A (C9H18O) forms a phenylhydrazone, but it gives a negative Tollens' test. The IR spectrum of A has a strong band near 1710 cm-1. The broadband proton decoupled 13C NMR spectrum of A is
Compound B (C8H12O2) shows a strong carbonyl absorption in its IR spectrum. The broadband proton-decoupled 13C NMR spectrum of B has only three signals, at δ 19 (CH3), 71 (C), and 216 (C). Propose a
(a) What would be the frequencies of the two absorption bands expected to be most prominent in the infrared spectrum of 4-hydroxycycloheptanone (C)? (b) In reality, the lower frequency band of these
One of the important reactions of benzylic alcohols, ethers, and esters is the ease of cleavage of the benzyl-oxygen bond during hydrogenation. This is another example of "hydrogenolysis," the
Dissolving formaldehyde in water leads to a solution containing primarily the gem-diol CH2(OH)2. Show the steps in its formation from formaldehyde.
When acetone is dissolved in water containing 18O instead of ordinary 16O (i.e., H2 18O instead of H2 16O), the acetone soon begins to acquire 18O and becomesThe formation of this oxygen-labeled
Shown below is the structural formula for sucrose (table sugar). Sucrose has two acetal groupings. Identify these.
Give an IUPAC systematic name for each of the following:(a)(b) (c) (d) (e)
Esters can also be synthesized by transesterificationIn this procedure we shift the equilibrium to the right by allowing the low-boiling alcohol to distill from the reaction mixture. The mechanism
(a) Write stereochemical formulas for compounds A-F:1.2. 3. 4. (b) Which of the last two methods, 3 or 4, would you expect to give a higher yield of F? Why?
Base-promoted hydrolysis of methyl mesitoate occurs through an attack on the alcohol carbon instead of the acyl carbon:(a) Can you suggest a reason that accounts for this unusual behavior? (b)
What products would you obtain from acidic and basic hydrolysis of each of the following amides?(a) N, N-Diethylbenzamide(b)(c)
(a) Provide the reagents required to accomplish the following transformation.(b) What product would you likely obtain if you attempted to synthesize the nitrile above by the following method?
Write structures for the products of the following reactions: (a) C6H5CH2OH + C6H5N==C==O →: (b) ClCOCl + excess CH3NH2 →: (c) Glycine (H3+NCH2CO2-) + C6H5CH2OCOCI →HO:- (d) Product of (c) +
Using decarboxylation reactions outline a synthesis of each of the following from appropriate starting materials: (a) 2-Hexanone (b) 2-Methylbutanoic acid (c) Cyclohexanone (d) Pentanoic acid
Diacyl peroxidesdecompose readily when heated. (a) What factor accounts for this instability? (b) The decomposition of a diacyl peroxide produces CO2. How is it formed? (c) Diacyl peroxides are often
Write a structural formula for each of the following compounds: (a) Octanoic acid (b) Propanamide (c) N, N-Diethylhexanamide (d) 2-Methyl-4-hexenoic acid (e) Butanedioic acid (f) 1,
Give an IUPAC systematic or common name for each of the following compounds:(a)(b) (c) (d) (e) (f) (g) (h) CH3CN
Experiments show that the molecular weight of acetic acid in the vapor state (just above its boiling point) is approximately 120. Explain the discrepancy between this experimental value and the true
Amides are weaker bases than corresponding amines. For example, most water-insoluble amines (RNH2) will dissolve in dilute aqueous acids (aqueous HCl, H2SO4, etc.) by forming water-soluble
While amides are much less basic than amines, they are much stronger acids. Amides have pKa values in the range 14-16, whereas for amines, pKa = 33-35.(a) What factor accounts for the much greater
What major organic product would you expect to obtain when acetyl chloride reacts with each of the following?(a) H2O(b) BuLi (excess)(c)(d) NH3 (excess) (e) (f) LiAlH(t-BuO)3 (g) NaOH/H2O (h)
What major organic product would you expect to obtain when acetic anhydride reacts with each of the following? (a) NH3 (excess) (b) H2O (c) CH3CH2CH2OH (d) C6H6 + AlCl3 (e) CH3CH2NH2 (excess) (f)
What major organic product would you expect to obtain when succinic anhydride reacts with each of the reagents given in Problem 17.23? In problem 17.23 (a) NH3 (excess) (b) H2O (c) CH3CH2CH2OH (d)
What products would you expect to obtain when ethyl propanoate reacts with each of the following? (a) H3O+, H2O (b) HO-, H2O (c) 1-Octanol, HCl (d) CH3NH2 (e) LiAlH4, then H2O (f) Excess
What products would you expect to obtain when propanamide reacts with each of the following? (a) H3O+, H2O (b) HO-, H2O (c) P4O10 and heat
What products would you expect to obtain when each of the following compounds is heated?(a) 4-Hydroxybutanoic acid(b) 3-Hydroxybutanoic acid(c) 2-Hydroxybutanoic acid(d) Glutaric acid(e)(f)
Write structural formulas for the major organic products from each of the following reactions.(a)(b) (c) (d) (e) (f) (g) (h)
Indicate reagents that would accomplish each of following transformations. More than one reaction may be necessary in some cases.(a)(b) (c) (d) (e) (f)
Which acid of each pair shown here would you expect to be stronger?(a)(b) (c) (d) (e)
Write structural formulas for the major organic products from each of the following reactions.(a)(b) (c) (d) (e)
Write structural formulas for the major organic products from each of the following reactions.(a)(b) (c) (d) (e)
Provide a detailed mechanism for each of the following reactions.(a)(b) (c)
On heating, cis-4-hydroxycyclohexanecarboxylic acid forms a lactone but trans-4-hydroxycyclohexanecarboxylic acid does not. Explain.
Show how p-chlorotoluene could be converted to each of the following:(a) p-Chlorobenzoic acid(b)(c) p-Chlorophenylacetic acid (d)
Indicate the reagents needed for each of the following syntheses. More than one step may be needed.(a)(b)
Show how pentanoic acid can be prepared from each of the following: (a) 1-Pentanol (b) 1-Bromobutane (two ways) (c) 5-Decene (d) Pentanal
The active ingredient of the insect repellent Off is N, N-diethyl-m-toluamide, m-CH3C6H4CON (CH2CH3)2. Outline a synthesis of this compound starting with 3-methylbenzoic acid (m-toluic acid).
Starting with benzene and succinic anhydride and using any other needed reagents, outline a synthesis of 1-phenylnaphthalene.
Write structural formulas for the following: (a) Methyl propanoate (b) Ethyl p-nitrobenzoate (c) Dimethyl malonate (d) N, N-Dimethylbenzamide (e) Pentanenitrile (f) Dimethyl phthalate (g) Dipropyl
Starting with either cis-or trans-HO2C--CH==CH--CO2H (i.e., either maleic or fumaric acid) and using any other needed compounds, outline syntheses of each of the following:(a)(b) (c)
Give stereochemical formulas for compounds A-Q:(a)(b)(c)(d)(e)(f)(g)
(R)-(+)-Glyceraldehyde can be transformed into (+)-malic acid by the following synthetic route. Give stereochemical structures for the products of each step.
R)-(+)-Glyceraldehyde can also be transformed into (-)-malic acid. This synthesis begins with the conversion of (R)-(+)-glyceraldehyde into (-)-tartaric acid, as shown in Problem 17.41, parts (e) and
Cantharidin is a powerful vesicant that can be isolated from dried beetles (Cantharis vesicatoria, or "Spanish fly"). Outlined here is the stereospecific synthesis of cantharidin reported by Gilbert
The IR and 1H NMR spectra of phenacetin (C10H13NO2) are given in Fig. 17.7. Phenacetin is an analgesic and antipyretic compound and was the P of A-P-C tablets (aspirin-phenacetin-caffeine). (Because
Given here are the 1H NMR spectra and carbonyl IR absorption peaks of five acyl compounds. Propose a structure for each.(a)(b) (c) (d) (e)
Compound X (C7H12O4) is insoluble in aqueous sodium bicarbonate. The IR spectrum of X has a strong absorption peak near 1740 cm-1, and its broadband proton-decoupled 13C spectrum is given in Fig.
Compound Y (C8H4O3) dissolves slowly when warmed with aqueous sodium bicarbonate. The IR spectrum of Y has strong peaks at 1779 and at 1854 cm-1. The broadband proton-decoupled 13C spectrum of Y
Show how each of the following compounds could be converted to benzoic acid:(a)(b) (c) (d) (e) Benzyl alcohol (f) Benzaldehyde

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