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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

The following five-step synthesis has been reported in the chemical literature. Suggest reagents appropriate for each step.
Increased “single-bond character” in a carbonyl group is associated with a decreased carbon–oxygen stretching frequency. Among the three compounds benzaldehyde, 2,4,6-trimethoxybenzaldehyde,
A compound has the molecular formula C4H8O and contains a carbonyl group. Identify the compound on the basis of its 1H NMR spectrum shown in Figure 17.17.
A compound (C7H14O) has a strong peak in its infrared spectrum at 1710 cm-1. Its 1H NMR spectrum consists of three singlets in the ratio 9:3:2 at δ 1.0, 2.1, and 2.3 ppm, respectively. Identify
Compounds A and B are isomeric diketones of molecular formula C6H10O2. The 1H NMR spectrum of compound A contains two signals, both singlets, at δ 2.2 (6 protons) and 2.8 ppm (4 protons). The 1H
A compound (C11H14O) has a strong peak in its infrared spectrum near 1700 cm-1. Its 200-MHz 1H NMR spectrum is shown in Figure 17.18. What is the structure of the compound?
A compound is a ketone of molecular formula C7H14O. Its 13C NMR spectrum is shown in Figure 17.19. What is the structure of the compound?
Compound A and compound B are isomers having the molecular formula C10H12O. The mass spectrum of each compound contains an abundant peak at m/z 105. The 13C NMR spectra of compound A (Figure 17.20)
Give an acceptable alkylamine or alkanamine name for each of the following amines:
Assign alkanamine names to N-methylethylamine and to N, Ndimethylcycloheptylamine.
Classify the following amine as primary, secondary, or tertiary, and give it an acceptable IUPAC name.
As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens. P-Nitroaniline, for example, is planar. Write a resonance form for p-nitroaniline that shows how
A chemistry handbook lists Kb for quinine as 1 x 10-6. What is pKb for quinine? What are the values of Ka and pKa for the conjugate acid of quinine?
Apply the Henderson–Hasselbalch equation (see “Quantitative Relationships Involving Carboxylic Acids,” the box accompanying Section 19.4) to calculate the CH3NH3 +/CH3NH2 ratio in water
The two amines shown differ by a factor of 40,000 in their Kb values. Which is the stronger base? Why? View their structures on Learning By Modeling. What are the calculated charges on the two
Each of the following is a much weaker base than aniline. Present a resonance argument to explain the effect of the substituent in each case.
Alkylation of ammonia is sometimes employed in industrial processes; the resulting mixture of amines is separated by distillation. The ultimate starting materials for the industrial preparation of
Which of the following amines can be prepared by the Gabriel synthesis? Which ones cannot? Write equations showing the successful applications of this method. (a) Butylamine (d)
Outline syntheses of each of the following arylamines from benzene: (a) o-Isopropylaniline (d) p-Chloroaniline (b) p-Isopropylaniline (e) m-Aminoacetophenone (c) 4-Isopropyl-1,
Show how you could prepare each of the following amines from benzaldehyde by reductive amination: (a) Benzylamine (c) N, N-Dimethylbenzylamine (b) Dibenzylamine (d) N-Benzylpiperidine
Give the structure of the major alkene formed when the hydroxide of each of the following quaternary ammonium ions is heated.
Outline syntheses of each of the following from aniline and any necessary organic or inorganic reagents: (a) p-Nitroaniline (c) p-Aminoacetanilide (b) 2, 4-Dinitroaniline
N-Nitroso amines are stabilized by electron delocalization. Write the two most stable resonance forms of N-nitrosodimethylamine, (CH3)2NNO.
Nitrous acid deamination of 2, 2-dimethylpropylamine, (CH3)3CCH2NH2, gives the same products as were indicated as being formed from 1, 1-dimethylpropylamine in Figure 22.5. Suggest a mechanism for
Design a synthesis of m-bromophenol from benzene.
Show by a series of equations how you could prepare m-bromoiodobenzene from benzene.
Show the proper sequence of synthetic transformations in the conversion of benzene to ethyl m-fluorophenyl ketone.
Cumene (isopropylbenzene) is a relatively inexpensive commercially available starting material. Show how you could prepare m-isopropylnitrobenzene from cumene.
Write structural formulas or build molecular models for all the amines of molecular formula C4H11N. Give an acceptable name for each one, and classify it as a primary, secondary, or tertiary amine.
Provide a structural formula for each of the following compounds: (a) 2-Ethyl-1-butanamine (b) N-Ethyl-1-butanamine (c) Dibenzylamine (d) Tribenzylamine (e) Tetraethylammonium hydroxide (f)
Many naturally occurring nitrogen compounds and many nitrogen-containing drugs are better known by common names than by their systematic names. A few of these follow. Write a structural formula for
(a) Give the structures or build molecular models and provide an acceptable name for all the isomers of molecular formula C7H9N that contain a benzene ring. (b) Which one of these isomers is the
Arrange the following compounds or anions in each group in order of decreasing basicity: (a) H3C-, H2N-, HO-, F- (b) H2O, NH3, HO-, H2N- (c) HO-, H2N-, C N, NO3
Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2, 4-Dichloroaniline, 2, 4-dimethylaniline, 2,
Physostigmine, an alkaloid obtained from a West African plant, is used in the treatment of glaucoma. Treatment of Physostigmine with methyl iodide gives a quaternary ammonium salt. What is the
Describe procedures for preparing each of the following compounds, using ethanol as the source of all their carbon atoms. Once you prepare a compound, you need not repeat its synthesis in a
Show by writing the appropriate sequence of equations how you could carry out each of the following transformations: (a) 1-Butanol to 1-pentanamine (b) tert-Butyl chloride to 2,
Each of the following dihaloalkanes gives an N-(haloalkyl) phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Write the structure of the phthalimide derivative formed
Give the structure of the expected product formed when benzylamine reacts with each of the following reagents: (a) Hydrogen bromide (b) Sulfuric acid (c) Acetic acid (d) Acetyl chloride (e)
Write the structure of the product formed on reaction of aniline with each of the following: (a) Hydrogen bromide (b) Excess methyl iodide (c) Acetaldehyde (d) Acetaldehyde and hydrogen (nickel
Write the structure of the product formed on reaction of acetanilide with each of the following: (a) Lithium aluminum hydride (e) tert-Butyl chloride, aluminum chloride (b) Nitric acid and
Identify the principal organic products of each of the following reactions:
Each of the following reactions has been reported in the chemical literature and proceeds in good yield. Identify the principal organic product of each reaction.
Provide a reasonable explanation for each of the following observations: (a) 4-Methylpiperidine has a higher boiling point than N-methylpiperidine.
Give the structures, including stereochemistry, of compounds A through C.
Devise efficient syntheses of each of the following compounds from the designated starting materials. You may also use any necessary organic or inorganic reagents. (a) 3,3-Dimethyl-1-butanamine from
Each of the following compounds has been prepared from p-nitroaniline. Outline a reasonable series of steps leading to each one. (a) p-Nitrobenzonitrile (d) 3, 5-Dibromoaniline (b) 3, 4,
Each of the following compounds has been prepared from o-anisidine (o-methoxyaniline). Outline a series of steps leading to each one. (a) o-Bromoanisole (d) 3-Fluoro-4-methoxybenzonitrile (b)
Design syntheses of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (a) p-Aminobenzoic acid from p-methylaniline
Ammonia and amines undergo conjugate addition to a, ß-unsaturated carbonyl compounds (Section 18.12). On the basis of this information, predict the principal organic product of each of the following
A number of compounds of the type represented by compound A were prepared for evaluation as potential analgesic drugs. Their preparation is described in a retrosynthetic format as shown.
Mescaline, a hallucinogenic amine obtained from the peyote cactus, has been synthesized in two steps from 3, 4, 5-trimethoxybenzyl bromide. The first step is nucleophilic substitution by sodium
Methamphetamine is a notorious street drug. One synthesis involves reductive amination of benzyl methyl ketone with methylamine. What is the structure of methamphetamine?
The basicity constants of N, N-dimethylaniline and pyridine are almost the same, whereas 4-(N,N-dimethylamino)pyridine is considerably more basic than either.
Compounds A and B are isomeric amines of molecular formula C8H11N. Identify each isomer on the basis of the 1H NMR spectra given in Figure 22.9.
The compound shown is a somewhat stronger base than ammonia. Which nitrogen do you think is protonated when it is treated with an acid? Write a structural formula for the species that results Refer
Does the 13C NMR spectrum shown in Figure 22.10 correspond to that of 1-amino-2-methyl-2-propanol or to 2-amino-2-methyl-1-propanol? Could this compound be prepared by reaction of an epoxide with
Show Lewis structures for these atoms:(a) Bromine(b) Calcium(c) Germanium
Show reaction equation using Lewis structures for the formation of these compounds from their elements:(a) Calcium chloride(b) Sodium sulfide
Show Lewis structures for the simplest neutral compounds formed from these elements:(a) Carbon and chlorine(b) Hydrogen and bromine
Show a Lewis structure for the simplest neutral compound formed from hydrogen and sulfur.
Discuss the stability of these structures:
Write Lewis structures for these compounds:(a) C3H8(b) C2H2(c) CH3N(d) NH3O
Using Lewis structures show a balanced equation for the reaction of H2O with HCl.
Calculate the formal charges on each of the atoms, except hydrogen's, of the molecules and determine the total charge of the species:
Predict which of the following constitutional isomers for the compound that is formed from one atom each of hydrogen, oxygen, and chlorine is more stable:
Experimental evidence indicates that the two oxygen of acetate ion are identical. Use resonance to explain this observation
Show the direction of the dipoles, if any, of these bonds:(a) C –– N(b) O –– N(c) O –– l(d) C –– Cl(e) B –– O(f) C –– Mg(g) C –– C(h) C –– H
Predict the geometry at the carbon of these compounds:
Predict the geometry of the following compounds at the indicated atoms:
Predict the direction of the dipole moments of these compounds:
Explain whether the bonds in these compounds would be ionic or covalent and show Lewis structures for them:(a) KC1(b) NC13(c) NaCN(d) KOH
What is the formula for the simplest neutral compound formed from P and H? Show a Lewis structure for this compound and predict its shape.
Show Lewis structures for these compounds:(a) CH5N (b) C2H5Cl (c) N2 (d) CH2S(e) C2H3F (f) CH4S
Calculate the formal charges on all of the atoms except hydrogen's, in these compounds:
Explain which of the two following structures would be more stable. Explain whether they represent isomers or are resonance structures.
Draw a Lewis structure for carbon monoxide (CO). Calculate the formal charges on the atoms and comment on the stability of this compound.
Use heavy and dashed wedged hues to show the shapes of the following molecules. Show the bond dipole of each polar bond and show the overall dipole of each molecule.
Predict the geometry at each atom, except hydrogen's, in these compounds:
(a) Show the unshared electron pairs on the following anion, The S has a formal charge of ? 1, and the formal charges of the other atoms are zero. (b) Draw a resonance structure for this ion,
Show a Lewis structure for C2H6O in which both carbons are bonded to the oxygen. What is the geometry of this molecule at the oxygen? Show the direction of the dipole for the molecule,
Show a Lewis structure for NO2–, both oxygen’s are bonded to the nitrogen.) Show a resonance structure also.
Amino acids, from which proteins are formed, exist as ?dipolar ions.? The structure of the dipolar ion of the amino acid alanine is (a) Calculate the formal charges on all of the atoms, except
A covalent ion can also have polar bonds. Consider the ammonium caution. I low arc its bonds polarized? Do you think that the N of the ammonium caution is more or less ?electro negative? than the N
You need to know the melting point for CaC12, for a lab report you are writing. Your lab partner says that the Handbook of Chemistry and Physics lists this as 68oC. Do you think you should trust that
Show a Lewis structure for A1C14–. What are the formal charges on the atoms of this anion? What is its shape?
Ammonium cyanate is composed of an ammonium caution (NH4+) and a cyanate anion (OCN–). Show a Lewis structure for the cyanate anion. (Both O and N are bonded to C.) Which atom has the negative
(a) Show a Lewis structure for urea. CH4N2O. Both N’s and the O are bonded to the C. The H’s are bonded to the N’s. None of the atoms has a formal charge.(b) Show a Lewis structure of an isomer
Phosphorus forms two compounds with chlorine, PCl3, and PCl5. The former follows the octet rule, but the latter does not. Show Lewis structures for each of these compounds. For the corresponding
On the basis of the rule that anything unusual about a structure must be shown explicitly, the nitrogen in the structure NH3 is seen to have an unshared pair of electrons whether these electrons are
Ozone O3 is a form of oxygen found in the upper atmosphere. It has the connectivity O— O—O and is neutral.(a) Show a Lewis structure for ozone.(b) Calculate the formal charge on each oxygen of
(a) Draw a Lewis structure for the carbonate anion CO32– each oxygen is bonded only to the carbon.(b) Calculate the formal charge on each atom.(c) What is the shape of this species?(d) Experimental
Consider the species CH3, which has three normal carbon—hydrogen bonds arid no other electrons on the carbon.(a) What is the charge of this species?(b) What is its geometry?(c) Discuss the
Explain how the dipole moments of FCl (0.9 D) and 1Cl (0.7 D) can be so similar.
Chlorine is more electronegative than phosphorus. Predict the dipole moment of PCl5.
Although carbon?carbon double bonds are shorter than carbon?carbon single bonds, all of the carbon?carbon bonds of benzene are the same length. Explain.
Explain whether or not these molecules are polar (have a dipole moment).(a) CBr4 (b) NH3 (c) CH3OCH3(d) CH2C12 (e) CO2
For each model, draw a structure that fits the geometry of the molecule. Then explain the geometry at each atom other than the hydrogen’s.
Draw a structure for each model. Explain whether the molecule represented by each model has a dipole moment or not.
Draw a structure for each model. Show the direction of the dipole moment for the molecule represented by each model.

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