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organic chemistry

Organic Chemistry 1st edition David R. Klein - Solutions

Consider the following compound:(a) How many signals do you expect in the 1H NMR spectrum of this compound?(b) Rank the protons in terms of increasing chemical shift.(c) How many signals do you expect in the 13C NMR spectrum?(d) Rank the carbon atoms in terms of increasing chemical shift. Br Н CI
Draw the expected1H NMR spectrum of the following compound: CI
For each of the following compounds, compare the two indicated protons and determine whether they are enantiotopic, homotopic, or diastereotopic:(a)(b)(c)(d)(e)(f)(g)(h)(i)(j)(k)(l)(m)(n)(o) CI. CI Me н Me CI `H.
A compound with molecular formula C8H18 exhibits a 1H NMR spectrum with only one signal. How many signals would you expect in the 13C NMR spectrum of this compound?
For each pair of compounds, identify how you would distinguish them using either1H NMR spectroscopy or13C NMR spectroscopy:(a)(b)(c)(d) 'CI CI CI
Predict the multiplicity of each signal in the1H NMR spectrum of the following compound:
How would you distinguish between the following compounds using13C NMR spectroscopy? ОН
How many signals would you expect in the13C NMR spectrum of each of the compounds in Problem 16.34?In Problem 16.34How many signals would you expect in the 1H NMR spectrum of each of the following compounds:(a)(b)(c)(d)(e)(f) CI Br ū-
How many signals would you expect in the1H NMR spectrum of each of the following compounds:(a)(b)(c)(d)(e)(f) CI Br ū-
A compound with molecular formula C17H36 exhibits a 1H NMR spectrum with only one signal. How many signals would you expect in the 13C NMR spectrum of this compound?
A compound with molecular formula C12H24 exhibits a 1H NMR spectrum with only one signal and a 13C NMR spectrum with two signals. Deduce the structure of this compound.
Each of the following compounds exhibits a 1H NMR spectrum with only one signal. Deduce the structure of each compound:(a) C5H10(b) C5H8Cl4(c) C12H18
Below are NMR spectra of several compounds. Identify whether these compounds are likely to contain ethyl, isopropyl, and/or tert-butyl groups:(a)(b)(c)(d) Proton NMR C3H12 Chemical Shift (ppm) Proton NMR CgH12O2 3 5.0 4.5 4.0 3.5 2.0 3.0 Chemical Shift (ppm) 1.5 1.0 0.5 25
Below are NMR spectra of several compounds. Identify whether these compounds are likely to contain ethyl, isopropyl, and/or tert-butyl groups:(a)(b)(c)(d) Proton NMR CH12 5 Chemical Shift (ppm) 6
A compound with molecular formula C7H14O exhibits the following13C NMR spectra:Several structures are consistent with these spectra. To determine which structure is correct, a 1H NMR spectrum was acquired which exhibits six signals. One of those signals is a singlet at 1.9 ppm with an integration
Determine the structure of an alcohol with molecular formula C5H12O that exhibits the following signals in its 13C NMR spectra:(a) Broadband decoupled: 73.8 δ, 29.1 δ, and 9.5 δ(b) DEPT-90: 73.8 δ(c) DEPT-135: positive signals at 73.8 δ and 9.5 δ; negative signal at 29.1 δ
Determine the structure of a compound with molecular formula C5H10O that exhibits the following broadband-decoupled and DEPT-135 spectra. The DEPT-90 spectrum has no signals. Broadband-decoupled 180 160 140 120 220 100 80 40 200 20 60 DEPT-135 220 180 120 200 160 140 100 80 40 20 60 Chemical Shift
Draw the structure of a compound with molecular formula C8H10 that exhibits five signals in its 13C NMR spectrum, four of which appear between 100 and 150 ppm.
Compare the following two constitutional isomers. The13C NMR spectrum of the first compound exhibits five signals, while the second compound exhibits six signals. Explain. Он НО.
For each of the following compounds, predict the number of signals and location of each signal in a13C NMR spectrum:(a)(b)(c)(d)(e)(f)(g)(h)(i)(j) H.
A compound with molecular formula C10H10O4 produces a 1H NMR spectrum that exhibits only two signals, both singlets. One signal appears at 3.9 ppm with a relative integration value of 79. The other signal appears at 8.1 ppm with a relative integration value of 52. Identify the structure of this
Propose a structure that is consistent with each of the following1H NMR spectra. In each case, the molecular formula is provided.(a)(b)(c)(d)(e)(f) Proton NMR C,H,,0 i ppm Integration Values 18.8 12.1 19.1 45.1 Foo Proton NMR C,H0 3.5 Integration Values 10.8 1.0 ppm 85.7 2.5 2.0 1.5 3.0
A chemist was attempting to achieve the following transformation:Mass spectrometry was then used to verify that the molecular formula of the major product was C7H15Br, just as expected. However, the 1H NMR spectrum of the product exhibited more than two signals. Identify what product was actually
How would you use1H NMR spectroscopy to distinguish between the following compounds?(a)(b)(c)(d)(e)(f) НО. но. Но. CI
The 1H NMR spectrum of a compound with molecular formula C7H14O3 exhibits only three signals, and all three signals appear above 2 ppm (downfield of 2 ppm) on the spectrum. Propose a structure for this compound.
Assign an IUPAC name for each of the following compounds:a.b.c.d. но, Он
Using any compounds that have no more than two carbon atoms, identify a method for preparing each of the following compounds:a.b.c.d. ОН ОН
Propose a plausible synthesis for each of the following transformations.a.b.c.d.e.f. H.
Identify the reagents that you would need to accomplish each of the following transformations.a.b. H.
Using any reagents of your choosing, show how you would convert tert-butyl alcohol into 2-methyl-1-propanol
Show at least two different methods for preparing 1-methylcyclohexene from 1-methylcyclohexanol.
Propose a plausible synthesis for each of the following transformations.a.b.c.d.e.f. он Он
Propose a synthesis for each of the following transformations.a.b.c.d. Br н н
Predict the major organic product for each of the following reactions.a.b.c.d.e.f. Но ? PCC Cн-Clz Н -он -ОН NazCrz07 H2SO4. H20
Two of the compounds from Problem 13.14 can be prepared from the reaction between a Grignard reagent and an ester. Identify those two compounds, and explain why the other four compounds cannot be prepared from an ester. ОН ОН
Determine whether each of the following compounds is optically active or optically inactive:a.b.c.d.e.f.g.h. Он Н, Me Me н ОН Et Me. .CI Н Me Н
Predict the products for each of the following transformations.a.b. ОН Нaso heat 1) TsCl, py -OH 2) NaOEt
Compound Y has molecular formula C7H12. Hydrogenation of compound Y produces methylcyclohexane. Treatment of compound Y with HBr in the presence of peroxides produces the following compound:Predict the products when compound Y undergoes ozonolysis. Br
For each of the following elimination reactions, assume a concerted process is taking place and draw the mechanism:a.b.c. NaOH 'CI LOTS NaOEt
Determine the hybridization state of each carbon atom in the following compounds:a.b. Н, н C=c=c=C Н н || Н `H.
Identify the reagents you would use to accomplish the following transformation. CI Он
When (R)-2-chloro-3-methylbutane is treated with potassium tert-butoxide, a monosubstituted alkene is obtained. When this alkene is treated with HBr, a mixture of products is obtained. Draw all of the expected products.
Although 2, 2-dimethylhexane has a molecular weight of 114, no peak is observed at m/z = 114. The base peak in the mass spectrum occurs at M–57.a. Draw the fragmentation responsible for formation of the M–57 ion.b. Explain why this cation is the most abundant ion to pass through the
Identify the reagents you would use to accomplish each of the following transformations.a.b.c.d.e.f. Br ОН Br ОН
Propose a plausible mechanism for the following transformation: Br2 Br Н,о*
Occasionally, carbocation rearrangements can be accomplished via the migration of a carbon atom other than a methyl group. Such an example follows. Identify the group that is migrating, and draw the curved arrow that shows the migration:
Identify the reagents you would use to achieve the following transformations:a.b. ОН Br Но Но ОН Br Но Но ОН
When a double bond has two identical groups (one on each vinylic position), we can use either cis-trans terminology or E-Z terminology:The configuration of this double bond can be designated as either trans or E. Both designations are acceptable. In most cases, cis = Z and trans = E. However, there
Draw the mechanism and predict the product of the following reaction. In this case, H3O+must be used as a proton source instead of water. Explain why. 1) xs MeMgBr 2) Hзо*
For each of the following alkenes, assign the configuration of the double bond as either E or Z:a.b.c.d. F.
Three of the compounds from Problem 13.14 can be prepared from the reaction between a hydride reducing agent (NaBH4 or LAH) and a ketone or aldehyde. Identify those three compounds, and explain why the other three compounds cannot be prepared via a hydride reducing agent.
Classify each of the following alkenes as mono-substituted, di-substituted, tri-substituted, or tetra-substituted:a.b.c.d.e.
In Section 4.2, we learned how to name bicyclic compounds. Using those rules, together with the rules discussed in this section, provide a systematic name for the following bicyclic compound:
For each of the following molecules, determine the number of carbon atoms present, and then determine the number of hydrogen atoms connected to each carbon atom:a.b.c.d.e.f.g.h.i.j.k.l. -z:
Below are mass spectra for four different compounds. Identify whether each of these compounds contains a bromine atom, a chlorine atom, or neither.a.b.c.d. 100- 80- 60- 60- 40 20- 0- 60 70 10 20 30 40 50 80 90 100 m/z Relative Intensity 100 80- 40 ot 10 20 30 40 50 60 70 80 06 100 110 m/z 80 20
While 13C is the main contributor to the (M+1)+• peak, there are many other elements that can also contribute to the (M+1)+• peak. For example, there are two naturally occurring isotopes of nitrogen. The most abundant isotope, 14N, represents 99.63% of all nitrogen atoms on Earth. The other
In the following reaction, determine whether the alkyne has been oxidized, reduced, or neither. Using the answer from the previous problem, try to determine the answer without calculating oxidation states, and then use the calculations to see if your intuition was correct. H2SO4. H20 HgSO4
When (1R, 2R)-2-bromocyclohexanol is treated with a strong base, an epoxide (cyclic ether) is formed. Suggest a mechanism for formation of the epoxide: он Strong base Br An epoxide
Consider the structure of cyclopentadiene and then answer the following questions:(a) How many sp3-hybridized carbon atoms are present in the structure of cyclopentadiene?(b) Identify the most acidic proton in cyclopentadiene. Justify your choice.(c) Draw all resonance structures of the conjugate
Draw all constitutional isomers with molecular formula C3H8O, and rank them in terms of increasing acidity.
Draw the expected1H NMR spectrum for each of the following compounds:(a)(b)(c) H. エ
Each of the three vinylic protons of styrene is split by the other two, and the J values are found to be Jab= 11 Hz, Jac = 17 Hz, and Jbc= 1 Hz. Using this information, draw the expected splitting pattern for each of the three signals (Ha, Hb, and Hc). Н, Нь На Styrene
Propose the structure for a compound that lacks a methyl group but nevertheless exhibits a quartet in its 1H NMR spectrum.
For each of the following compounds, determine the multiplicity of each signal in the expected1H NMR spectrum:(a)(b)(c)(d)
The 1H NMR spectrum of a compound with molecular formula C7H15Cl exhibits two signals with relative integration 2 : 3. Propose a structure for this compound.
A compound with molecular formula C4H6O2has the following NMR spectrum. Determine the number of protons giving rise to each signal. Proton NMR 25 2.0 2.0 1.5 ppm 3.0 Integration Values 5.0 4.5 4.0 18.92 3.5 19.77 19.46
A compound with molecular formula C10H10O has the following NMR spectrum. Determine the number of protons giving rise to each signal. Proton NMR 10 3 1 ppm 4 87.1| 18.7 Integration Values 17.1 51.1
A compound with molecular formula C5H10O2has the following NMR spectrum. Determine the number of protons giving rise to each signal. Proton NMR lle 2.0 1.5 0.5 ppm 4.5 4.0 33.2 3.5 3.0 2.5 1.0 Integration Values 48.4 33.3 48.7
For each of the following compounds, identify the expected chemical shift for each type of proton:(a)(b)(c)(d) н н ОН
A1H NMR spectrum was acquired for each of the following two compounds. One spectrum exhibits two signals downfield of 2.0 ppm, while the other spectrum exhibits only one signal downfield of 2.0 ppm. Match each spectrum with its corresponding compound.
A1H NMR spectrum was acquired for each of the following constitutional isomers. Comparison of the spectra reveals that only one of these spectra exhibits a signal between 6 and 7 ppm. Identify the structure that corresponds with this spectrum.
Predict the chemical shifts for the signals in the 1H NMR spectrum of each of the following compounds:(a)(b)(c)(d)(e)
Identify the structure of a compound with molecular formula C9H20 that exhibits four CH2 groups, all of which are chemically equivalent. How many total signals would you expect in the 1H NMR spectrum of this compound?
We saw a general rule that the two protons of a CH2group will be chemically equivalent if there are no chirality centers in the compound. An example of an exception is 3-bromopentane. This compound does not possess a chirality center. Nevertheless, the two highlighted protons are not chemically
Identify the number of signals expected in the1H NMR spectrum of each of the following compounds.(a)(b)(c)(d)(e)(f)(g)(h)(i)(j)(k)(l) OMe MeO.
Identify the structure of a compound with molecular formula C5H12 that exhibits only one kind of proton. That is, all 12 protons are chemically equivalent.
Butane (C4H10) exhibits only two different kinds of protons, shown here in red and blue.(a) Explain why all four protons shown in red are chemically equivalent.(b) Explain why all six protons shown in blue are chemically equivalent.(c) How many different kinds of protons are present in pentane?(d)
For each of the following compounds, determine whether the two protons shown in red are homotopic, enantiotopic, or diastereotopic:(a)(b)(c)(d)(e) OMe Н. Н CI H,
In the mass spectrum of bromobenzene (Figure 15.27), the base peak appears at m/z = 77.Figure 15.27a) Does this fragment contain Br? Explain your reasoning.b) Draw the cationic fragment that represents the base peak. 100 Br 80 60 40- 20 50 25 75 100 125 150 175 m/z Relative Abundance
Show how you would use a Grignard reaction to prepare each compound below.a.b.c.d.e.f. OH
Draw a bond-line structure for each of the following compounds:a. 3-Isopropyl-2, 4-dimethyl-2-penteneb. 4-Ethyl-2-methyl-2-hexenec. 1, 2-Dimethylcyclobutene (The name of a cycloalkene will not include a locant to specify the position of the π bond, because, by definition, it is assumed to be
Draw a mechanism and predict the major product of the following reaction. 1) Excess LAH 2) H30*
Compound X has molecular formula C7H14. Hydrogenation of compound X produces 2, 4-dimethylpentane. Hydroboration-oxidation of compound X produces a racemic mixture of 2, 4-dimethylpentan-1-ol (shown below). Predict the major product(s) obtained when compound X is treated with aqueous acid (H3O+).
Provide a systematic name for each of the following compounds:a.b.c.d.
Most common amines (RNH2) exhibit pKavalues between 35 and 45. R represents the rest of the compound (generally carbon and hydrogen atoms). However, when R is a cyano group, the pKais found to be drastically lower:(a) Explain why the presence of the cyano group so drastically impacts the pKa.(b)
Cyclopropane (shown below) has only one constitutional isomer. Draw a condensed structure of that isomer. Н-С. Т Сн- CH2 H2Č
Propose a molecular formula for a compound that exhibits the following peaks in its mass spectrum.a) (M)+• at m/z = 72, relative height = 38.3% of base peak(M+1)+• at m/z = 73, relative height = 1.8% of base peakb) (M)+• at m/z = 68, relative height = 100% (base peak)(M+1)+• at m/z = 69,
Draw a mechanism and predict the major product for each reaction.a.b.c.d.e.f. ? 1) LAH H. 2) H20
Using acetylene and methyl bromide as your only sources of carbon atoms, propose a synthesis for each of the following compounds:(a)(b) En Et Me En Et Me
Propose a mechanism for the following transformation: ОН Он Но
Below is the structure of rilpivirine, a promising new anti-HIV drug that combats resistant strains of HIV. Its ability to side-step resistance will be discussed in the upcoming chapter.(a) Identify the two most acidic protons in rilpivirine.(b) Identify which of these two protons is more acidic.
Identify the number of sp3-hybridized carbon atoms in the following compound:(CH3)2C = CHC(CH3)3
Below are the structures of two common over-the-counter pain relievers. Determine the hybridization state of each carbon atom in these compounds:a.b. TH. H H H. .C. TH. .C: .Č. `H Н Acetylsalicyclic acid (aspirin) Dーエ Н Н. н. нн Н. Н. H. Н I II II :O. Н. C. н ннн н Ibuprofen
Consider the reaction below. The rate of this reaction is markedly increased if a small amount of sodium iodide is added to the reaction mixture. The sodium iodide is not consumed by the reaction and is therefore considered to be a catalyst. Explain how the presence of iodide can speed up the rate
Predict which of the following compounds is more acidic, and explain your choice. N- -N- -NH2 NH2
Sigma bonds experience free rotation at room temperature:In contrast, Ï€ bonds do not experience free rotation. Explain. н Н. cec с—н Н-С€с н `H Н
In Chapter 9, we learned about addition of water across a Ï€ bond. Identify whether the alkene has been oxidized, reduced, or neither. (First look at each carbon atom separately, and then look at the net change for the alkene as a whole.) н Он H3o*
The following compound can react rapidly via an SN1 process. Explain why this primary substrate will undergo an SN1 reaction so rapidly. OTs
Identify which two compounds below are constitutional isomers: (CH].Cнӧсн,сH, (CH),cӧсн, (CH),снӧсн,
Consider the structure of formaldehyde:a) Identify the type of bonds that form the C = O double bond.b) Identify the atomic orbitals that form each C = H bond.c) What type of atomic orbitals do the lone pairs occupy? .C. H. Formaldehyde

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