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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Rank the compounds in each of the following groups in order of decreasing acidity: (a) Acetic acid, ethane, ethanol (b) Benzene, benzoic acid, benzyl alcohol (c) Propanedial, 1, 3-propanediol,
Identify the more acidic compound in each of the following pairs: (a) CF3CH2CO2H or CF3CH2CH2CO2H (b) CH3CH2CH2CO2H or CH3C≡CCO2H
Propose methods for preparing butanoic acid from each of the following: (a) 1-Butanol (e) 2-Propanol (b) Butanal (f) Acetaldehyde (c) 1-Butene (g) CH3CH2CH (CO2H) 2 (d) 1-Propanol
It is sometimes necessary to prepare isotopically labeled samples of organic substances for probing biological transformations and reaction mechanisms. Various sources of the radioactive mass-14
Give the product of the reaction of pentanoic acid with each of the following reagents: (a) Sodium hydroxide (b) Sodium bicarbonate (c) Thionyl chloride (d) Phosphorus tribromide (e) Benzyl
Show how butanoic acid may be converted to each of the following compounds: (a) 1-Butanol (e) Phenyl propyl ketone (b) Butanal (f) 4-Octanone (c) 1-Chlorobutane (g) 2-Bromobutanoic acid (d)
Show by a series of equations, using any necessary organic or inorganic reagents, how acetic acid can be converted to each of the following compounds: (a) H2NCH2CO2H (e) ICH2CO2H (b) C6H5OCH2CO2H
Each of the following reactions has been reported in the chemical literature and gives a single product in good yield. What is the product in each reaction?
Show by a series of equations how you could synthesize each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (a) 2-Methylpropanoic
a) Which stereoisomer of 4-hydroxycyclohexanecarboxylic acid (cis or trans) can form a lactone? Make a molecular model of this lactone. What is the conformation of the cyclohexane ring in the
Suggest reasonable explanations for each of the following observations. (a) Both hydrogens are anti to each other in the most stable conformation of formic acid. (b) Oxalic acid has a dipole moment
When compound A is heated, two isomeric products are formed. What are these two products?
A certain carboxylic acid (C14H26O2), which can be isolated from whale blubber or sardine oil, yields nonanal and O=CH(CH2)3CO2H on ozonolysis. What is the structure of this acid?
When levulinic acid (CH3CCH2CH2CO2H) was hydrogenated at high pressure over a nickel catalyst at 220°C, a single product, C5H8O2, was isolated in 94% yield. This compound lacks hydroxyl absorption
On standing in dilute aqueous acid, compound A is smoothly converted to mevalonolactone.
Suggest reaction conditions suitable for the preparation of compound A from 5-hydroxy-2-hexynoic acid.
In the presence of the enzyme aconitase, the double bond of aconitic acid undergoes hydration. The reaction is reversible, and the following equilibrium is established:
The 1H NMR spectra of formic acid (HCO2H), maleic acid (cis-HO2CCH=CHCO2H), and malonic acid (HO2CCH2CO2H) are similar in that each is characterized by two singlets of equal intensity. Match these
Compounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra. Compound A: δ 1.3 ppm (3H, triplet); 3.6 ppm (2H, quartet); 4.1 ppm
Compounds A and B are carboxylic acids. Identify each one on the basis of its 1H NMR spectrum. (a) Compound A (C3H5ClO2) (Figure 19.10). (b) Compound B (C9H9NO4) has a nitro group attached to an
The list of carboxylic acids in Table 19.1 is by no means exhaustive insofar as common names are concerned. Many others are known by their common names, a few of which follow. Give a systematic IUPAC
Write a structural formula for each of the following compounds: (a) 2-Phenylbutanoyl bromide (e) 2-Phenylbutanamide (b) 2-Phenylbutanoic anhydride (f) N-Ethyl-2-phenylbutanamide (c) Butyl
The 1H NMR spectrum of N, N-dimethylformamide shows a separate signal for each of the two methyl groups. Can you explain why?
Write the structure of the tetrahedral intermediate formed in each of the reactions given in Problem 20.3. Using curved arrows, show how each tetrahedral intermediate dissociates to the appropriate
Benzoic anhydride has been prepared in excellent yield by adding one molar equivalent of water to two molar equivalents of benzoyl chloride. How do you suppose this reaction takes place?
Write a structural formula for the acyl cation intermediate in the preceding reaction.
Apply the knowledge gained by studying Table 20.3 to help you predict the major organic product of each of the following reactions:
Write the structure of the tetrahedral intermediate formed in each of the reactions given in Problem 20.7. Using curved arrows, show how each tetrahedral intermediate dissociates to the appropriate
The compound having the structure shown was heated with dilute sulfuric acid to give a product having the molecular formula C5H12O3 in 63–71% yield. Propose a reasonable structure for this product.
On the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Figure 20.4, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.
In a similar experiment, unlabeled 4-butanolide was allowed to stand in an acidic solution in which the water had been labeled with 18O. When the lactone was extracted from the solution after 4 days,
Trimyristin is obtained from coconut oil and has the molecular formula C45H86O6. On being heated with aqueous sodium hydroxide followed by acidification, trimyristin was converted to glycerol and
In a similar experiment, pentyl acetate was subjected to saponification with 18O-labeled hydroxide in 18O-labeled water. What product do you think became isotopically labeled here, acetate ion or
On the basis of the general mechanism for basic ester hydrolysis shown in Figure 20.5, write an analogous sequence of steps for the saponification of ethyl benzoate.
Give the structure of the expected product of the following reaction:
Write the structure of the tetrahedral intermediate formed in the reaction just described.
Write an equation showing the preparation of the following amides from the indicated carboxylic acid derivative:
Phthalimide has been prepared in 95% yield by heating the compound formed on reaction of phthalic anhydride (Section 20.4) with excess ammonia. This compound has the molecular formula C8H10N2O3. What
On the basis of the general mechanism for amide hydrolysis in acidic solution shown in Figure 20.6, write an analogous sequence of steps for the hydrolysis of acetanilide,
On the basis of the general mechanism for basic hydrolysis shown in Figure 20.7, write an analogous sequence for the hydrolysis of N, N-dimethylformamide,
Outline an efficient synthesis of 1-propanamine (CH3CH2CH2NH2) from butanoic acid.
Show how ethyl alcohol could be used to prepare (a) CH3CN and (b) CH3CH2CN. Along with ethyl alcohol you may use any necessary inorganic reagents.
Suggest a reasonable mechanism for the conversion of a nitrile (RCN) to the corresponding amide in aqueous acid.
Write an equation showing how you could prepare ethyl phenyl ketone from propanenitrile and a Grignard reagent. What is the structure of the imine intermediate?
Give an acceptable IUPAC name for each of the following compounds:
Write a structural formula for the principal organic product or products of each of the following reactions: (a) Acetyl chloride and bromobenzene, AlCl3 (b) Acetyl chloride and 1-butanethiol (c)
Using ethanol as the ultimate source of all the carbon atoms, along with any necessary inorganic reagents, show how you could prepare each of the following: (a) Acetyl chloride (f) Ethyl
Using toluene as the ultimate source of all the carbon atoms, along with any necessary inorganic reagents, show how you could prepare each of the following: (a) Benzoyl chloride (f) Benzyl
The saponification of 18O-labeled ethyl propanoate was described in Section 20.10 as one of the significant experiments that demonstrated acyl–oxygen cleavage in ester hydrolysis. The 18O-labeled
Suggest a reasonable explanation for each of the following observations: (a) The second-order rate constant k for saponification of ethyl trifluoroacetate is over 1 million times greater than that
The preparation of cis-4-tert-butylcyclohexanol from its trans stereoisomer was carried out by the following sequence of steps. Write structural formulas, including stereochemistry, for compounds A
The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give a compound A.
Ambrettolide is obtained from hibiscus and has a musk-like odor. Its preparation from a compound A is outlined in the table that follows. Write structural formulas, ignoring stereochemistry, for
Outline reasonable mechanisms for each of the following reactions: Discuss.
Identify compounds A through D in the following equations:
When compounds of the type represented by A are allowed to stand in pentane, they are converted to a constitutional isomer.
(a) In the presence of dilute hydrochloric acid, compound A is converted to a constitutional isomer, compound B.
Poly (vinyl alcohol) is a useful water-soluble polymer. It cannot be prepared directly from vinyl alcohol, because of the rapidity with which vinyl alcohol (CH2=CHOH) isomerizes to acetaldehyde.
(a) Assuming the first step in the polymerization of methyl methacrylate is as shown,
A certain compound has a molecular weight of 83 and contains nitrogen. Its infrared spectrum contains a moderately strong peak at 2270 cm-1. Its 1H and 13C NMR spectra are shown in Figure 20.10. What
A compound has a molecular formula of C8H14O4, and its infrared spectrum contains an intense peak at 1730 cm-1. The 1H NMR spectrum of the compound is shown in Figure 20.11. What is its structure?
A compound (C4H6O2) has a strong band in the infrared at 1760 cm 1. Its 13C NMR spectrum exhibits signals at δ 20.2 (CH3), 96.8 (CH2), 141.8 (CH), and 167.6 ppm (C). The 1H NMR spectrum of the
The common names and structural formulas of a few aldehydes follow. Provide an IUPAC name.
Convert each of the following functional class IUPAC names to a substitutive name. (a) Dibenzyl ketone (b) Ethyl isopropyl ketone (c) Methyl 2, 2-dimethylpropyl ketone (d) Allyl methyl ketone
Show how 2-butanone could be prepared by a procedure in which all of the carbons originate in acetic acid (CH3CO2H).
Chloral is one of the common names for trichloroethanal. A solution of chloral in water is called chloral hydrate; this material has featured prominently in countless detective stories as the
The hydroxyl group of a cyanohydrin is also a potentially reactive site. Methacrylonitrile is an industrial chemical used in the production of plastics and fibers. One method for its preparation is
Write a stepwise mechanism for the formation of benzaldehyde diethyl acetal from benzaldehyde and ethanol under conditions of acid catalysis.
Write the structures of the cyclic acetals derived from each of the following. (a) Cyclohexanone and ethylene glycol (b) Benzaldehyde and 1, 3-propanediol (c) Isobutyl methyl ketone and ethylene
Asked you to write a mechanism describing formation of benzaldehyde diethyl acetal from benzaldehyde and ethanol, write a stepwise mechanism for the acid hydrolysis of this acetal.
Acetal formation is a characteristic reaction of aldehydes and ketones, but not of carboxylic acids. Show how you could advantageously use a cyclic acetal protecting group in the following synthesis:
Write the structure of the carbinolamine intermediate and the imine product formed in the reaction of each of the following: (a) Acetaldehyde and benzylaminek, C6H5CH2NH2 (b) Benzaldehyde and
Write the structure of the carbinolamine intermediate and the enamine product formed in the reaction of each of the following: (a) Propanal and dimethylamine, CH3NHCH3 (b) 3-Pentanone and
Identify the alkene product in each of the following Wittig reactions
Can you write a resonance structure for (C6H5) P -CH2 in which neither phosphorus nor carbon has a formal charge? (Hint: Remember phosphorus can have more than eight electrons in its valence shell.)
What combinations of carbonyl compound and ylide could you use to prepare each of the following alkenes?
(a) Showed the preparation of 3-methyl-3-heptene by a Wittig reaction involving the ylide shown. Write equations showing the formation of this ylide beginning with 2-bromobutane
Using Figure 17.12 as a guide, write a mechanism for the Baeyer–Villiger oxidation of cyclohexyl methyl ketone by peroxybenzoic acid.
Baeyer–Villiger oxidation of aldehydes yields carboxylic acids (e.g., m-nitrobenzaldehyde yields m-nitrobenzoic acid). What group migrates to oxygen?
(a) Write structural formulas and provide IUPAC names for all the isomeric aldehydes nd Ketones that have the molecular formula C5H10O, Include stereoisomers. (b) Which of the isomers in part (a)
Each of the following aldehydes or ketones is known by a common name. It’s substitutive IUPAC name is provided in parentheses. Write a structural formula for each one. (a) Chloral (2, 2,
Predict the product of the reaction of Propanal with each of the following: (a) Lithium aluminum hydride (b) Sodium borohydride (c) Hydrogen (nickel catalyst) (d) Methylmagnesium iodide, followed
Hydride reduction (with LiAlH4 or NaBH4) of each of the following ketones has been reported in the chemical literature and gives a mixture of two diastereomeric alcohols in each case. Give the
Choose which member in each of the following pairs reacts faster or has the more favorable equilibrium constant for reaction with the indicated reagent. Explain your reasoning.
Equilibrium constants for the dissociation (Kdiss) of cyanohydrins according to the equation
Each of the following reactions has been reported in the chemical literature and gives a single organic product in good yield. What is the principal product in each reaction?
Wolff–Kishner reduction (hydrazine, KOH, ethylene glycol, 130°C) of the compound shown gave compound A. Treatment of compound A with m-chloroperoxybenzoic acid gave compound B, which on reduction
On standing in 17O-labeled water, both formaldehyde and its hydrate are found to have incorporated the 17O isotope of oxygen. Suggest a reasonable explanation for this observation.
Reaction of benzaldehyde with 1, 2-octanediol in benzene containing a small amount of p-toluenesulfonic acid yields almost equal quantities of two products in a combined yield of 94%. Both products
Compounds that contain both carbonyl and alcohol functional groups are often more stable as cyclic hemiacetals or cyclic acetals than as open-chain compounds. Examples of several of these are shown.
Compounds that contain a carbon–nitrogen double bond are capable of stereoisomerism much like that seen in alkenes.
Compounds known as lactones, which are cyclic esters, are formed on Baeyer–Villiger oxidation of cyclic ketones. Suggest a mechanism for the Baeyer–Villiger oxidation shown.
Organic chemists often use enantiomerically homogeneous starting materials for the synthesis of complex molecules (see Chiral Drugs, p. 273). A novel preparation of the S enantiomer of compound B has
Suggest reasonable mechanism for each of the following reactions:
Amygdalin, a substance present in peach, plum, and almond pits, is a derivative of the R enantiomer of benzaldehyde cyanohydrin. Give the structure of (R)-benzaldehyde cyanohydrin.
Using ethanol as the source of all the carbon atoms, describe efficient syntheses of each of the following, using any necessary organic or inorganic reagents:
Describe reasonable syntheses of Benzophenone, from each of the following starting materials and any necessary inorganic reagents. (a) Benzoyl chloride and benzene (b) Benzyl alcohol and
The sex attractant of the female winter moth has been identified as the tetraene CH3(CH2)8CH═CHCH2CH═CHCH2CH═CHCH═CH2. Devise a synthesis of this material from 3,
Hydrolysis of a compound a in dilute aqueous hydrochloric acid gave (along with methanol) a compound B, mp 164–165°C. Compound B had the molecular formula C16H16O4; it exhibited hydroxyl
Syntheses of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short

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