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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Which of the following alkyl halides could be successfully used to form a Grignard reagent?a. HOCH2CH2CH2CH2Brb.c. d. H2NCH2CH2CH2Br
Starting with (R)-1-deuterio-1-propanol, how could you prepare:a. (S)-1-deuterio-1-propanol? b. (S)-1-deuterio-1-methoxypropane? c. (R)-1-deuterio-1-methoxypropane?
What alkenes would you expect to be obtained from the acid-catalyzed dehydration of 1 hexanol?
Give the product of each of the following reactions:a.b. c. d. e. f. g. h.
When heated with H2SO4both 3,3-dimethyl-2-butanol and 2,3-dimethyl-2-butanol are dehydrated to form 2,3-dimethyl-2-butene. Which alcohol dehydrates more rapidly?
Using the given starting material, any necessary inorganic reagents, and any carbon containing compounds with no more than two carbon atoms, indicate how the following syntheses could be carried
Propose a mechanism for the following reaction:
When deuterated phenanthrene oxide undergoes an epoxide rearrangement in water, 81% of the deuterium is retained in the product.a. What percentage of the deuterium will be retained if an NIH shift
When 3-methyl-2-butanol is heated with concentrated HBr, a rearranged product is obtained. When 2-methyl-1-propanol reacts under the same conditions, a rearranged product is not obtained. Explain.
When the following seven-membered ring alcohol is dehydrated, three alkenes are formed:Propose a mechanism for their formation.
Show how 1-butanol can be converted into the following compounds:a. CH3CH2CH2CH2Brb.c. CH3CH2CH2CH2OCH3 d. CH3CH2CH2CH2NHCH2CH3 e. CH3CH2CH2CH2SH f. CH3CH2CH2CH2C==N
How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?
Ethylene oxide reacts readily with because of the strain in the three-membered ring. Cyclopropane has approximately the same amount of strain, but does not react with. HO-. Explan
Which of the following ethers would be obtained in greatest yield directly from alcohols?
Propose a mechanism for each of the following reactions:a.b.
Indicate how each of the following compounds could be prepared, using the given starting material:a.b. c. d. e. CH3CH2CH ===CH2†’ CH3CH2CH2CH2CH2CH2CH2CH3
Triethylene glycol is one of the products obtained from the reaction of ethylene oxide and hydroxide ion. Propose a mechanism for its formation.
Give the major product expected from the reaction of 2-ethyloxirane with each of the following reagents: a. 0.1 M HCl b. CH3OH/H+ c. ethyl magnesium bromide in ether, followed by 0.1 M HCl d. 0.1 M
When ethyl ether is heated with excess HI for several hours, the only organic product obtained is ethyl iodide. Explain why ethyl alcohol is not obtained as a product.
a. Propose a mechanism for the following reaction:b. A small amount of a product containing a six-membered ring is also formed. Give the structure of that product.c. Why is so little six-membered
Identify A through H.
Explain why the acid-catalyzed dehydration of an alcohol is a reversible reaction, whereas the base-promoted dehydrohalogenation of an alkyl halide is an irreversible reaction
Greg Nard added an equivalent of 3,4-epoxy-4-methylcyclohexanol to an ether solution of methyl magnesium bromide and then added dilute hydrochloric acid. He expected that the product would be a diol.
An ion with a positively charged nitrogen atom in a three-membered ring is called an aziridinium ion. The following aziridinium ion reacts with sodium methoxide to form A and B:If a small amount of
Dimerization is a side reaction that occurs during the preparation of a Grignard reagent. Propose a mechanism that accounts for the formation of the dimer.
Propose a mechanism for each of the following reactions:a.b.
One method used to synthesize an epoxide is to treat an alkene with an aqueous solution of followed by an aqueous solution of sodium hydroxide. a. Propose a mechanism for the conversion of
Which of the following reactions occurs most rapidly? Why?a.b. c.
When bromobenzene reacts with propene in a Heck reaction, two constitutional isomers are obtained as products. Give the structures of the products and explain why two products are obtained.
A vicinal diol has OH groups on adjacent carbons. The dehydration of a vicinal diol is accompanied by a rearrangement called the pinacol rearrangement. Propose a mechanism for this reaction.
Although 2-methyl-1,2-propanediol is an asymmetrical vicinal diol, only one product is obtained when it is dehydrated in the presence of acid.a. What is this product? b. Why is only one product
What product is obtained when the following vicinal diol is heated in an acidic solution?
What product would be formed if the preceding alcohol were heated with an equivalent amount of HBr rather than with a catalytic amount of H2SO4?
Two stereoisomers are obtained from the reaction of cyclopentene oxide and dimethylamine. The R,R-isomer is used in the manufacture of eclanamine, an antidepressant. What other isomer is obtained?
Propose a mechanism for each of the following reactions:a.b.
List the following alcohols in order of decreasing rate of dehydration in the presence of acid:
Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether. It is not a good method for preparing an unsymmetrical ether such as ethyl propyl ether. a.
How could you distinguish the mass spectrum of 2,2-dimethylpropane from those of pentane and 2-methylbutane?
How could their mass spectra distinguish the following compounds?
Identify the ketones that are responsible for the mass spectra shown in Figure 13.9.
Using curved arrows, show the principal fragments that would be observed in the mass spectrum of each of the following compounds:a.b.c.d.e.f.
Two products are obtained from the reaction of (Z)-2-pentene with water and a trace of H2SO4. The mass spectra of these products are shown in Figure 13.10. Identify the compounds responsible for the
a. Which is higher in energy per photon, electromagnetic radiation with wavenumber 100 cm-1 or with wavenumber 2000 cm-1? b. Which is higher in energy per photon, electromagnetic radiation with
a. Radiation of what wavenumber has a wavelength of 4μm? b. Radiation of what wavelength has a wavenumber of 200 cm-1?
Which would be expected to be more intense, the stretching vibration of a C==O bond or the stretching vibration of a C==C bond?
Which will occur at a larger wavenumber? 1. a C≡≡C stretch or a C==C stretch 2. a C--H stretch or a C--H bend 3. a C--N stretch or a C==N stretch b. Assuming that the force constants are the
Which will occur at a larger wavenumber? a. The C--N stretch of an amine or the C--N stretch of an amide b. The C--O stretch of phenol or the C--O stretch of cyclohexanol c. The C==O stretch of a
Which would show an absorption band at a larger wavenumber: a carbonyl group bonded to an sp3 hybridized carbon or a carbonyl group bonded to an sp2 hybridized carbon?
What m zvalue is most likely for the base peak in the mass spectrum of 3-methylpentane?
List the following compounds in order of decreasing wavenumber of the C==O absorption band:a.b. c.
Which will show an O--H stretch at a higher wavenumber, ethanol dissolved in carbon disulfide or an undiluted sample of ethanol?
a. Why is an O--H stretch more intense than an N--H stretch? b. Why is the O--H stretch of a carboxylic acid broader than the O--H stretch of an alcohol?
How does one know that the absorption band at ~ 1100 cm-1 in Figure 13.26 is due to a C--O bond and not to a C--N bond?
a. An oxygen-containing compound shows an absorption band at ~ 1700 cm-1 and no absorption bands at ~ 3300 cm-1, ~ 2700 cm-1,or ~ 1100 cm-1. What class of compound is it? b. A nitrogen-containing
How could IR spectroscopy distinguish between the following? a. a ketone and an aldehyde b. a cyclic ketone and an open-chain ketone c. benzene and cyclohexene d. cis-2-hexene and trans-2-hexene e.
For each of the following pairs of compounds, give one absorption band that could be used to distinguish between them:a.b. c. d. e. f.
The mass spectrum and infrared spectrum of an unknown compound are shown in Figures 13.27 and 13.28, respectively. Identify the compound.
A compound with molecular formula C4H6O gives the infrared spectrum shown in Figure 13.34. Identify the compound.
Which peak would be more intense in the mass spectrum of the following compounds the peak at or the peak at m/z = 71? a. 3-methylpentane b. 2-methylpentane
List three factors that influence the intensity of an IR absorption band.
For each of the following pairs of compounds, identify one IR absorption band that could be used to distinguish between them:a.b. c. d. e. f. g. h. i. cis-2-butene and trans-2-butene j. CH3CH2CH2OH
a. How could you determine by IR spectroscopy that the following reaction had occurred?b. After purifying the product, how could you determine that all the NH2 NH2 had been removed?
What identifying characteristics would be present in the mass spectrum of a compound containing two bromine atoms?
Assuming that the force constant is approximately the same for C--C, C--N, and C--O bonds, predict the relative positions of their stretching vibrations.
A mass spectrum shows significant peaks at m/z = 87, 115, 140, and 143. Which of the following compounds is responsible for that mass spectrum: 4,7-dimethyl-1-octanol, 2,6-dimethyl-4-octanol, or
How could IR spectroscopy distinguish between 1,5-hexadiene and 2,4-hexadiene?
A compound gives a mass spectrum with peaks at m/z = 77 (40%), 112 (100%), 114 (33%), and essentially no other peaks. Identify the compound.
What hydrocarbons will have a molecular ion peak at m/z = 112?
The "nitrogen rule" states that if a compound has an odd-mass molecular ion, the compound contains an odd number of nitrogen atoms. a. Calculate m/z the value for the molecular ion of the following
In the following boxes, list the types of bonds and the approximate wavenumber at which each type of bond is expected to show an IR absorption:
For each of the IR spectra in Figures 13.35, 13.36, and 13.37, four compounds are shown. In each case, indicate which of the four compounds is responsible for the spectrum.a.b. c.
What peaks in their mass spectra would be used to distinguish between 4-methyl-2 pentanone and 2-methyl-3-pentanone?
A compound is known to be one of those shown here. What absorption bands in the compound's IR spectrum would allow you to identify the compound.
How could IR spectroscopy distinguish among 1-hexyne, 2-hexyne, and 3-hexyne?
For each of the IR spectra in Figures 13.38, 13.39, and 13.40, indicate which of the five given compounds is responsible for the spectrum.a.b. c.
Each of the IR spectra shown in Figure 13.41 is the spectrum of one of the following compounds. Identify the compound that is responsible for each spectrum.a. b. c.
Predict the major characteristic IR absorption bands that would be given by each of the following compounds:a.b. c. d. e. f.
Given that the force constants are similar for C--H and C--C bonds, explain why the stretching vibration of a bond occurs at a greater wavenumber.
The IR spectrum of a compound with molecular formula C5H8O was obtained in CCl4 and is shown in Figure 13.42. Identify the compound.
The mass spectrum of an unknown compound has a molecular ion peak with a relative intensity of 43.27% and an M + 1 peak with a relative intensity of 3.81%. How many carbon atoms are in the compound?
The IR spectrum shown in Figure 13.43 is the spectrum of one of the following compounds. Identify the compound.
The IR spectrum shown in Figure 13.44 is the spectrum of one of the following compounds. Identify the compound.
Determine the molecular formula of a saturated acyclic hydrocarbon with an M peak at m/z = 100 with a relative intensity of 27.32%, and an M + 1 peak with a relative intensity of 2.10%.
Calculate the approximate wavenumber at which a C==C stretch will occur, given that the force constant for the C==C bond is 10 × 105 gs-2.
The IR and mass spectra for three different compounds are shown in Figures 13.45-13.47. Identify each compound.a.b. c.
Which molecular formula has an exact molecular mass of 86.1096 amu: C6H14, C4H10N2, or C4H6O2?
Sketch the mass spectrum of 1-chloropropane.
The mass spectra of 1-methoxybutane, 2-methoxybutane, and 2-methoxy-2-methylpropane are shown in Figure 13.7. Match the compounds with the spectra.
Primary alcohols have a strong peak at m/z = 31. What fragment is responsible for this peak?
What frequency (in MHz) is required to cause a proton to flip its spin when it is exposed to a magnetic field of 1 tesla?
One of the spectra in Figure 14.6 is due to 1-chloropropane, and the other to 1-iodopropane. Which is which?
In each of the following compounds, which of the underlined protons has the greater chemical shift (i.e., the farther downfield signal or the higher frequency signal)?a.b. c. d. e.
In each of the following pairs of compounds, which of the underlined protons has the greater chemical shift (i.e., the farther downfield signal or the higher frequency signal)?a.b. c.
Without referring to Table 14.1, label the protons in the following compounds. The proton that gives the signal at the lowest frequency should be labeled a, the next b, etc.a.b. c. d. e. f. g. h. i.
How would integration distinguish the 1H NMR spectra of the following compounds?
The 1H NMR spectrum shown in Figure 14.8 corresponds to one of the following compounds. Which compound is responsible for this spectrum?
[18]-Annulene shows two signals in its 1H NMR spectrum: one at 9.25 ppm and the other very far upfield (beyond TMS) at - 2.88 ppm. What hydrogens are responsible for each of the signals?
Using a diagram like the one in Figure 14.13, predicta. the relative intensities of the peaks in a tripletb. the relative intensities of the peaks in a quintet
The 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown in Figure 14.14. Identify the carboxylic acids. (The "offset" notation means that the signal has been moved to the
a. Calculate the magnetic field (in tesla) required to flip an 1H nucleus in an NMR spectrometer that operates at 360 MHz. b. What strength magnetic field is required when a 500-MHz instrument is

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