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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

The compound whose structure isIs best named (IUPAC) (a) 3, 5-dimethylcyclopentyl ether (b) 3,5-dimethylcyclopentane-oxo (c) cis-3,5-dimethyloxacyclohexane. (d) trans-3,5- dimethyloxacyclohexane?
The first step in the detailed mechanism for the dehydration of 1-propanol with concentrated H2SO4 would be (a) Loss of OH- (b) Formation of a sulfate ester (c) Protonation of the alcohol (d) Loss of
Identify the nucleophile in the following reaction: RX + H2O -→ ROH + H+X- (a) X- (b) H+ (c) H2O (d) ROH (e) RX
Which is the method of choice for preparing the ether (CH2CH2)3 COCH3? (a) CH3Br + (CH3CH2)3CO-K+ (b) (CH3CH2)3 COH + CH3MgBr (c) (CH3CH2)3 CMgBr + CH3OH (d) (CH3CH2)3 CBr + CH3O-K+
Where on the chart presented in Figure 10-2 would the following be located: AM radio waves (v ~ 1 MHz = 1000 kHz = 106 Hz = 106 s-1, or cycles s-1); FM broadcast frequencies (v ~ 100 MHz = 108 s-1)?
Convert each of the following quantities into the specified units, (a) 1050 cm-1 into (, in (m; (b) 510 nm (green light) into v, in s-1 (cycles s-1, or hertz); (c) 6.15 (m into v̄, in cm-1; (d) 2250
Convert each of the following quantities into energies, in kcal mol-1. (a) A bond rotation of 750 wavenumbers (cm-1); (b) A bond vibration of 2900 wavenumbers (cm-1); (c) An electronic transition of
Calculate to three significant figures the amount of energy absorbed by a hydrogen when it undergoes an (-to-( spin flip in the field of (a) A 2.11-T magnet (v = 90 MHz); (b) An 11.75-T magnet {v =
For each of the following changes, indicate whether it corresponds to moving to the right or the left in an NMR spectrum, (a) Increasing radio frequency (at constant magnetic field strength); (b)
Sketch a hypothetical low-resolution NMR spectrum showing the positions of the resonance peaks for all magnetic nuclei for each of the following molecules. Assume an external magnetic field of 2.11
If the NMR spectra of the molecules in Problem 30 were recorded by using high resolution for each nucleus, what differences would be observed?
The 1H NMR spectrum of CH3COCH2C(CH3)3, 4,4-dimethyl-2-pentanone, taken at 300 MHz shows signals at the following positions: 307, 617, and 683 Hz downfield from tetramethylsilane (a) What are the
Order the 1H NMR signals of the following compounds by chemical-shift position (lowest to highest). Which one is the most upheld? The most downfield?(a) H3C-CH3(b) H2C==CH2(c) H3C-O-CH3(d)(e) (f)
Which hydrogens in the following molecules exhibit the more downfield signal relative to (CH3)4 Si in the NMR experiment? Explain.(a) (CH3)2O or (CH3)3N(b)(c) (d) (CH3)2S or (CH3)2S==O
How many signals would be present in the 1H NMR spectrum of each of the cyclopropane derivatives shown below? Consider carefully the geometric environments around each hydrogen.(a)(b) (c) (d) (e)
1H NMR spectra for two haloalkanes are shown below. Propose structures for these compounds that are consistent with the spectra.(a) C5H11C1, spectrum A;(b) C4H8Br2, spectrum B.
The following 1H NMR signals are for three molecules with ether functional groups. All the signals are singlets (single, sharp peaks). Propose structures for these compounds, (a) C3H8O2, ( = 3.3 and
(a) The 1H NMR spectrum of a ketone with the molecular formula C6Hl2O has ( = 1.2 and 2.1 ppm (ratio 3:1). Propose a structure for this molecule. (b) Each of two isomeric molecules related to the
List the four important features of 1H NMR and the information you can derive from them.
Describe in which ways the 1H NMR spectra of the compounds below would be similar and how they would differ. Address each of the four issues you listed in Problem 41. To which compound class does
Below are shown three C4H8C12 isomers on the left and three sets of 1H NMR data that one would expect on application of the simple N + 1 rule on the right. Match the structures to the proper spectral
The 1H NMR chemical shifts are given for each of the following compounds.-As best you can, assign each signal to the proper group of hydrogens in the molecule and sketch a spectrum for each compound,
A hydrocarbon with the formula C6H14 gives rise to 'H NMR spectrum G (margin). What is its structure? This molecule has a structural feature similar to that of another compound whose spectrum is
Treatment of the alcohol corresponding to NMR spectrum D in Problem 47 with hot concentrated HBr yields a substance with the formula C5H11Br. Its 1H NMR spectrum exhibits signals at ( = 1.0 (t, 3 H),
The 1H NMR spectrum of 1-chloropentane is shown at 60 MHz (spectrum H) and 500 MHz (spectrum I), Explain the differences in appearance of the two spectra, and assign the signals to specific hydrogens
Propose a reasonable structure for each of the following molecules on the basis of the given molecular formula and of the 1H and proton-decoupled l3C NMR data(a) C7H16O, spectra J and K (* = CH2 by
The 1H NMR spectrum of cholesteryl benzoate is shown as spectrum N. Although complex, il contains a number of distinguishing features. Analyze the absorptions marked by integrated values. The inset
The tcrpcne a-terpineol has the molecular formula C10H18O and is a constituent of pine oil. As the -ol ending in the name suggests, it is an alcohol. Use its 1H NMR spectrum (spectrum O, p. 443) to
Study of the solvolysis of derivatives of menthol [5-methyl 2 (I methylethyl) cyclohexanol] has greatly enhanced our understanding of these types of reactions. Heating the isomer of the
The molecule (CH3)4Si (tetramethylsilane) is used as an internal standard in 1H NMR spectroscopy. One of the following properties makes it especially useful. Which one? (a) Highly paramagnetic (b)
One of the following compounds will show a doublet as part of its 'H NMR spectrum. Which one?(a) CH4(b) ClCH(CH3)2(c) CH3CH2CH3(d)
In the1'H NMR spectrum of 1-fluorobutane, the most deshielded hydrogens are those bound to (a) C4 (b) C3 (c) C2 (d) C1
One of the following compounds will have one peak in its 'H NMR spectrum and two peaks in its l3C NMR spectrum. Which one?(a)(b) (c) CH3--CH3 (d) (e)
Draw the structures of the molecules with the following names. (a) 4,4-Dichloro-trans-2-octene (b) (Z)-4-bromo-2-iodo-2-pentene (c) 5-Methyl.cis-3-hexen-l-ol (d) (R)-l,3-Dichlorocycloheptene (e)
Name each of the following molecules in accord with the IUPAC system of nomenclature.a.b. c. d. e. f. g. h. i.
Name each of the compounds below. Use cis / trans and/or E/Z designations, if appropriate, to designate stereochemistrya.b. c.
Of each pair of the following compounds, which one should have the higher dipole moment the higher boiling point? (a) cis- or trans-1,2-Difluoroethene; (b) Z- or E-1,2-difluoropropene: (c) Z- or
Draw the structures of each of the following compounds, rank them in order of acidity, and circle the most acidic hydrogen(s) in each: cyclopentane, cyclopentanol, cyclopentene, 3-cyclopenten-l-ol.
Assign structures to the following molecules on the basis of the indicated 'H NMR spectra A-E Consider stereochemistry, where applicable(a) C4H7C1, NMR spectrum A;(b) C5H8O2, NMR spectrum B;(c)
Explain the splitting patterns in 1HNMR spectrum D in detail. The insets are fivefold expansions
For each of the pairs of alkenes below, indicate whether measurements of polarity alone would be sufficient to distinguish the compounds from one another. Where possible, predict which compound would
Place the alkenes in each group in order of increasing stability of the double bond and increasing heat of hydrogenation.a.b. c. d. e.
Write the structures of as many simple alkenes as you can that, upon catalytic hydrogenation with H2 over Pt. will give as the product (a) 2-methylbutane: (b) 2.3-dimethylbutane; (c)
The reaction between 2-bromobutane and sodium ethoxide in ethanol gives rise to three E2 products. What are they? Predict their relative amounts.
What key structural feature distinguishes haloalkanes that give more than one stereoisomer on E2 elimination from those that give only a single isomer exclusively?
Write the most likely major product(s) of each of the following haloalkanes with sodium ethoxide in ethanol or potassium tert-butoxide in 2-methyl-2-propanol (tert-butyl alcohol), (a)
Referring to the data in Chapter Integration Problem 11-27 predict how the rate of E2 reaction between 1-bromopropane and sodium ethoxide in ethanol would compare with those of the three substrates
Draw Newman projections of the four stereo-isomers of 2-bromo-3-methylpentane in the conformation required for E2 elimination. Are the reactive conformations also the most stable conformations?
Referring to the answer to Problem 38 of Chapter 7, predict (qualitatively) the relative amounts of isomeric alkenes that are formed in the elimination reactions shown.
Referring to the answers to Problem 30 of Chapter 9, predict (qualitatively) the relative yields of all the alkenes formed in each reaction
Compare and contrast the major products of dehydrohalogenation of 2-chloro-4-methylpentane with (a) Sodium ethoxide in ethanol and (b) Potassium tert-butoxide in 2-methyl-2-propanol (tert-butyl
Referring to Problem 59 of Chapter 7, write the structure of the alkene that you would expect to be formed as the major product from E2 elimination of each of the chlorinated steroids shown.
1-Methylcyclohexene is more stable than methylene-cyclohexane (A, in the margin), but methylene-cyclopropane (B) is more stable than 1-methyl-cyclopropene. Explain.
Give the products of bimolecular elimination from each of the following isomeric halogenated compounds.a.b. One of these compounds undergoes elimination 50 times faster than the other. Which compound
Explain in detail the differences between the mechanisms giving rise to the following two experimental results.
The molecular formulas and 13C NMR data (in ppm) for several compounds are given here. The type of carbon, as revealed from DEPT spectra, is specified in each case. Deduce a structure for each
Data from both ordinary and DEPT l3C NMR spectra for several compounds with the formula C5H10 are given here. Deduce a structure for each compound, (a) 25.3 (CH2); (b) 13.3 (CH3), 17.1 (CH3), 25.5
From the Hooke's law equation, would you expect the C-X bonds of common haloalkanes (X = Cl, Br, 1) to have IR bands at higher or lower wave numbers than are typical for bonds between carbon and
Convert each of the following IR frequencies into micrometers. (a) 1720 cm-1 (C=0) (b) 1650 cm-1 (C=C) (c) 3300 cm-1 (O-H) (d) 890 cm-1 (alkene bend) (e) 1100 cm-1 (C-O) (f) 2260 cm-1 (C=N)
Match each of the following structures with the IR data that correspond best. Abbreviations: w. weak; m, medium: s, strong; br, broad,(a) 905 (s), 995 (m), 1040 (m), 1640 (m), 2850-2980 (s), 3090
An organic compound exhibits IR spectrum F. From the group of structures below, choose one that matches the spectrum best.
The three compounds hexane. 2-methylpentane and 3-methylpentane correspond to the three mass spectra shown below. Match each compound with the spectrum that best fits its structure on the basis of
Assign as many peaks as you can in the mass spectrum of 1-bromopropane (Figure 11-24).
The following table lists selected mass-spectral data for three isomeric alcohols with the formula C5H12O. On the basis of the peak positions and intensities, suggest structures for each of the three
Calculate the degree of un-saturation that corresponds to each of the following molecular formulas, (a) C7H12 (b) C8H7NO2; (c) C6C16; (d) C10H22O11 (e) C6H10S; (f) C18H28O2
A hydrocarbon with an exact molecular mass of 96.0940 exhibits the following spectroscopic data: 1H NMR Î´ = 1.3 (m, 2 H), 1.7 (m, 4 H), 2.2 (m, 4 H), and 4.8 (quin, J = 3 Hz, 2 H) ppm;
The isolation of a novel form of molecular carbon C60 was reported in 1990. The substance has the shape of a soccer ball of carbon atoms and possesses the nickname "buckyball" (you don't want to know
You have just been named president of the famous perfume company. Scents "R" Us Searching for a hot new item to market, you run across a bottle labeled only C10lH26O, which contains a liquid with a
Using the information in Table 11-4 match up each set of the following IR signals with one of these naturally occurring compounds, camphor, menthol, chrysanthemic ester, epiandrosterone you can find
Identify compounds A, B, and C from the following information and explain the chemistry that is taking place. Reaction of the alcohol shown in the margin with 4-methylbenzenesulfonyl chloride in
The citric acid cycle is a series of biological reactions that plays a central role in cell metabolism. The cycle includes dehydration reactions of both malic and citric acids, yielding fumaric and
The following data indicate that the dehydration of certain amino acid derivatives is stereo-specific.Divide the task of analyzing these data among you to determine the nature of the stereo
What is the empirical formula of compound A (see margin)? (a) C8H14; (b) C8HI6; (c) C8H12; (d) C4H7
What is the degree of un-saturation in cyclobutane? (a) Zero (b) One (c) Two (d) Three
Which of the following molecules would have the lowest heat of hydrogenation?a.b. c. d.
A certain hydrocarbon containing eight carbons was found to have two degrees of un-saturation but no absorption bands in the IR spectrum at 1640 cm-1. The best structure for this compound isa.b. c. d.

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