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organic chemistry

Organic Chemistry 1st edition David R. Klein - Solutions

In each of the following transformations, identify whether the starting material has been oxidized, reduced, or neither. Try to determine the answer without calculating Oxidation states, and then use the calculations to see if your intuition was correct.a.b.c.d.e.f. CI. CI - 3
When butyl bromide is treated with sodium iodide in ethanol, the concentration of iodide quickly decreases but then slowly returns to its original concentration. Identify the major product of the reaction.
Consider the following two compounds. These compounds are stereoisomers of 1,2,3-trimethylcyclohexane. One of these compounds has three chirality centers, while the other compound has only two chirality centers. Identify which compound has only two chirality centers and explain why.
Cyclopropane is a compound in which the carbon atoms form a three-membered ring:Each of the carbon atoms in cyclopropane is sp3 hybridized. Cyclopropane is more reactive than other cyclic compounds (four-membered rings, five-membered rings, etc.). Analyze the bond angles in cyclopropane and explain
In each of the following transformations, identify whether the starting material has been oxidized, reduced, or neither. Try to determine the answer without calculating Oxidation states, and then use the calculations to see if your intuition was correct.a.b.c.d.e.f. CI CI но. ОН H.
There are only four constitutional isomers with molecular formula C4H9NO2 that contain a nitro group (-NO2). Three of these isomers have similar pKa values, while the fourth isomer has a much higher pKa value. Draw all four isomers, and identify which one has the higher pKa. Explain your choice.
Consider the following compound with molecular formula C4H8O:(a) Draw a constitutional isomer that you expect will be approximately one trillion (1012) times more acidic than the compound above.(b) Draw a constitutional isomer that you expect will be less acidic than the compound above.(c) Draw a
Consider the pKavalues of the following constitutional isomers:Using the rules that we developed in this chapter (ARIO), we might have expected these two compounds to have the same pKa. Nevertheless, they are different. Salicylic acid is apparently more acidic than its constitutional isomer. Can
Identify reagents that can be used to achieve each of the following transformations:(a) To convert 1-hexene into a primary alcohol(b) To convert 3, 3-dimethyl-1-hexene into a secondary alcohol(c) To convert 2-methyl-1-hexene into a tertiary alcohol
Propose a plausible mechanism for the following tautomerization process: Н. CHз CH3 Н,о
Suggest an efficient synthesis for the following transformation: Он En Br
When the following ester is treated with lithium iodide in DMF, a carboxylate ion is obtained:(a) Draw the mechanism of this reaction.(b) When the methyl ester is used as the substrate, the reaction is 10 times faster:Explain the increase in rate. LiI DMF LiI Mel DMF
Identify the reagents that you would use to accomplish each of the following transformations:a.b.c.d.e.f. -Br OH
Propose a mechanism for the following transformation: он I. Н,о
You are given a solution containing a pair of enantiomers (A and B). Careful measurements show that the solution contains 98% A and 2% B. What is the ee of this solution?
Identify whether each of the following compounds is chiral or achiral:a.b.c.d.e.f.g.h.i.j.k.l.m.n.o.p. CI
Draw the alkoxide formed in each of the following cases:a.b.c.d. HO ? Na NaH ОН
Mandelate esters exhibit spasmolytic activity (they act as muscle relaxants). The nature of the alkyl group (R) greatly affects potency. Research indicates that the optimal potency is achieved when R is a nine-carbon chain (a nonyl group). Explain why nonyl mandelate is more potent than either
Provide an IUPAC name for each of the following alcohols:a.b.c.d.e. HO. Br Br
Each of the following compounds contains two carbonyl groups. Identify which carbonyl group will exhibit a signal at lower wave number.a.b.c. O:
1-Butyne was treated with sodium amide followed by ethyl iodide. An IR spectrum of the product was acquired and then compared with the spectrum of the starting alkyne. A signal at 2200 cm-1 was observed in the IR spectrum of the starting alkyne, but the same signal was not observed in the IR
In Chapter 21, we will explore how nitriles can be converted into carboxylic acids. How would you use IR spectroscopy to monitor the progress of this reaction? R-CEN A nitrile Н,о* C. он A carboxylic acid
Describe how IR spectroscopy might be used to monitor the progress of each of the following reactions.a.b.c.d.e. Na, Cr,0, H,SO,, H,0 HO, HO.
Describe how IR spectroscopy might be used to monitor the progress of each of the following reactions.a.b.c.d.e. Na,Cr,07 H,SO, H,0 ОН ОН .Н CH3 N. CH;I N.
Chrysanthemic acid is isolated from chrysanthemum flowers. The IR spectrum of chrysanthemic acid exhibits five signals above 1500 cm-1. Identify the source for each of these signals. Он (+)-trans-Chrysanthemic acid
Match each compound with the appropriate IR spectrum:a.b.c.d.e.f. `NH2 но но он 100- 60- 20- 4000 3500 3000 2500 2000 1500 1000 Wavenumber (cm-1) % Transmittance
Carefully consider the structure of 2, 3-dimethyl-2-butene. There are twelve Csp3—H bonds, and they are all identical. Nevertheless, there is more than one signal just to the right of 3000 cm-1 in the IR spectrum of this compound. Can you offer an explanation?
For each of the following IR spectra, determine whether it is consistent with the structure of a ketone, an alcohol, a carboxylic acid, a primary amine, or a secondary amine.a.b.c.d.e.f. 100- 80- 60- 20- 0. 2500 Wavenumber (cm-) 4000 3500 3000 2000 1500 1000 % Transmittance 100 80- 60- 40- 20-
For each of the following IR spectra, identify whether it is consistent with the structure of an alcohol, a carboxylic acid, or neither.a.b.c.d.e.f. 100- 80- 60- 40 20- 0. 2000 4000 3500 3000 2500 1500 1000 Wavenumber (cm-1) % Transmittance 100 80 60- 40 20- 4000 3500 3000 2500 2000 1500 1000
As explained previously, the concentration of an alcohol can be selected such that both a broad signal and a narrow signal appear simultaneously. In such cases, the broad signal is always to the right of the narrow signal, never to the left. Explain.
Trans-2-Butene does not exhibit a signal in the double bond region of the spectrum (1600–1850 cm-1); however, IR spectroscopy is still helpful in identifying the presence of the double bond. Identify the other signal that would indicate the presence of a C = C bond.
The C = C bond in 2-cyclohexenone produces an unusually strong signal. Explain using resonance structures. O=
For each pair of compounds, determine which C = C bond will produce a stronger signal.a.b. CI
For each pair of compounds, determine which C = C bond will produce a stronger signal.a.b. CI CI CI
Compare the wave number of absorption for the following two C = C bonds. Use resonance structures to explain why the C = C bond in the conjugated compound produces a signal at lower wave number. 1650 cm-1 1600 cm-
For each of the following compounds, determine whether or not you would expect its IR spectrum to exhibit a signal to the left of 3000 cm-1a.b.c..d.e.f.
For each of the following compounds, rank the highlighted bonds in terms of increasing wave number:a.b. TH. 0= H.
The SN2 reaction between a Grignard reagent and an epoxide works reasonably well when the epoxide is ethylene oxide. However, when the epoxide is substituted with groups that provide steric hindrance, a competing reaction can dominate, in which an allylic alcohol is produced. Propose a mechanism
Using bromobenzene and ethylene oxide as your only sources of carbon, show how you could prepare trans- 1, 2-diphenyloxirane (a racemic mixture of enantiomers). + Enantiomer
Propose a plausible synthesis for the following transformation. Enantiomer ОН
Draw a Lewis structure for each of the compounds below:a) CH2 = CHOCH2CH(CH3)2 b) (CH3CH2)2CHCH2CH2OHc) (CH3CH2)3COHd) (CH3)2C = CHCH2CH3e) CH2 = CHCH2OCH2CH(CH3)2 f) (CH3CH2)2C = CH2g) (CH3)3CCH2CH2OH h) CH3CH2CH2CH2CH2CH3i) CH3CH2CH2OCH3j) (CH3CH2CH2)2CHOHk)
Consider the structures of 2-nitrophenol and 3-nitrophenol. These compounds have very different pKa values. Predict which one has the lower pKa, and explain why. (In order to solve this problem, you must draw the structure of each nitro group.) ОН ОН „NO2 `NO2 2-Nitrophenol 3-Nitrophenol
Consider the following substitution reaction:a) Determine whether this reaction proceeds via an SN1 or SN2 process.b) Draw the mechanism of this reaction.c) What is the rate equation of this reaction?d) Would the reaction occur at a faster rate if the concentration of cyanide were doubled?e) Draw
For each of the following pairs of alcohols, identify the one that is more acidic, and explain your choice:a.b.c.d.e. но но F. OH
Draw all constitutional isomers with molecular formula C2H6S, and rank them in terms of increasing acidity.
For each of the following compounds, use the nitrogen rule to determine whether the molecular weight should be even or odd. Then calculate the expected m/z value for the molecular ion.a.b.c.d. O: O:
A compound with molecular formula C5H11N has no p bonds. Every carbon atom is connected to exactly two hydrogen atoms. Determine the structure of the compound.
Propose a plausible mechanism for the following transformation: ОН |Н,о+ Он
Predict the major product(s) of the following reaction: Br2 H2S
Draw an energy diagram of a reaction with the following characteristics:(a) A one-step reaction with a negative ΔG(b) A one-step reaction with a positive ΔG(c) A two-step reaction with an overall negative ΔG, where the intermediate is higher in energy than the reactants and the first transition
For each of the following reactions determine whether Î”S for the reaction (Î”Ssys) will be positive, negative, or approximately zero:a.b.c.d.e. Br НBr HCI CI
Which value of ΔG corresponds with Keq < 1?(a) +1 kJ/mol(b) 0 kJ/mol(c) -1 kJ/mol
Which value of ΔG corresponds with Keq = 1?(a) +1 kJ/mol(b) 0 kJ/mol(c) - 1 kJ/mol
How would you distinguish between each pair of compounds using mass spectrometry?a.b. N.
Draw the structure of each of the following compounds:a. (R)-3, 3-Dibromocyclohexanolb. (S)-2, 3-Dimethyl-3-pentanolc. (1S, 2S, 4R)-Bicyclo [2.2.1] heptan-2-ol
With current spectroscopic techniques (discussed in Chapters 15–17), chemists are generally able to determine the structure of an unknown organic compound in just one day. These techniques have only been available for the last several decades. In the first half of the twentieth century, structure
Identify which of the following two reactions you would expect to occur more rapidly: (1) addition of HBr to 2-methyl-2- pentene or (2) addition of HBr to 4-methyl-1-pentene. Explain your choice.
Determine the electron configuration for each of the following ions:a. A carbon atom with a negative chargeb. A carbon atom with a positive charge c. A nitrogen atom with a positive charged. An oxygen atom with a negative charge
Provide an IUPAC name for each of the following alcohols:a.
When 1-chlorobutane is treated with sodium hydroxide, two products are formed. Identify the two products, and explain how these products could be distinguished using IR spectroscopy.
Cyclopentanone was treated with lithium aluminum hydride followed by H3O+. Explain what you would look for in the IR spectrum of the product to verify that the expected reaction had occurred. Identify which signal should be present and which signal should be absent.
Identify the alkene that would yield the following products via ozonolysis:a.b.c.d. Н Н
Rank the following anions in terms of increasing basicity: ное
Draw all constitutional isomers with molecular formula C5H10 that possess one p bond.
Starting with acetylene as your only source of carbon atoms, propose a plausible synthesis for 1, 4-dioxane: 1,4-Dioxane
Starting with acetylene as your only source of carbon atoms, identify how you would prepare each member of the following homologous series of aldehydes:a. Ethanal b. Propanalc. Butanald. Pentanal
Single bonds generally experience free rotation at room temperature:Nevertheless, the €œsingle bond€ shown below exhibits a large barrier to rotation. In other words, the energy of the system is greatly increased if that bond is rotated. Explain the source of this energy
Identify the reagents you might use to achieve each of the following transformations: Br Br но, En
Identify the reagents you would use to accomplish each of the following transformations: Br Но. Но -ОН Br Но ОН Br он нин ОН En он Он En
In each case below, identify the acid and the base. Then draw the curved arrows showing a proton transfer reaction. Draw the products of that proton transfer, and then predict the position of equilibrium.(a)(b)(c) LIOH
Consider the following two compounds:a) Identify which of these two compounds has greater resonance stabilization.b) Would you expect compound C (below) to have a resonance stabilization that is more similar to compound A or to compound B? Compound B Compound A
In the previous problem, we saw that an acetylide ion can attack a variety of electrophiles. In Chapter 20, we will see that a C=O bond can also function as an electrophile. Consider the following reaction between an acetylide ion (the nucleophile) and a ketone (the electrophile):The acetylide ion
Identify the reagents you would use to accomplish each of the following transformations: Он Br ОН он Он Br -Br Он En Br En Он
In each case below, identify the acid and the base. Then draw the curved arrows showing a proton transfer reaction. Draw the products of that proton transfer, and then predict the position of equilibrium.(a)(b)(c) LIOH
In the compound below, identify all carbon atoms that are electron deficient (Î´+) and all carbon atoms that are electron rich (Î´-). Justify your answer with resonance structures. Н н H.
The following reaction does not produce the desired product, but does produce a product that is a constitutional isomer of the desired product. Draw the product that is obtained, and propose a mechanism for its formation: ОН Он 1) NaNH2 2) MeI
The following reaction is observed to be regioselective. Draw a mechanism for the reaction, and explain the source of regioselectivity in this case: Br HEг.
For each compound below, identify the most acidic proton in the compound:(a)(b)(c)(d)(e)(f)(g)(h) -NH2 н- Н—
Ramelteon is a hypnotic agent used in the treatment of insomnia:a) What is the molecular formula of this compound?b) How many sp3-hybridized carbon atoms are present in this structure?c) How many sp2-hybridized carbon atoms are present in this structure?d) How many sp-hybridized carbon atoms are
In this chapter, we have seen that an acetylide ion can function as a nucleophile and attack an alkyl halide in an SN2 process. More generally speaking, the acetylide ion can attack other electrophiles as well. For example, we will see in Chapter 14 that epoxides function as electrophiles and are
Cycloserine is an antibiotic isolated from the microbe Streptomyces orchidaceous. It is used in conjunction with other drugs for the treatment of tuberculosis.a) What is the molecular formula of this compound?b) How many sp3-hybridized carbon atoms are present in this structure?c) How many
Compound X is treated with Br2 to yield meso-2,3- dibromobutane. What is the structure of compound X?
For each reaction below, draw the mechanism (curved arrows) and then predict which side of the reaction is favored under equilibrium conditions.(a)(b)(c)(d) ОН ное Н H.
Propose at least two different structures for a compound with six carbon atoms that exhibits the following features:a. All six carbon atoms are sp2 hybridized.b. Only one carbon atom is sp hybridized, and the remaining five carbon atoms are all sp3 hybridized (remember that your compound can have
Propose a plausible synthesis for each of the following transformations:a.b.c.d.e. HO,
Explain why each of the following alcohols cannot be prepared via hydroboration-oxidation:a.b.c. ОН Он
HA has a pKa of 15, while HB has a pKa of 5. Draw the equilibrium that would result upon mixing HB with NaA. Does the equilibrium favor formation of HA or of HB?
Using any compounds that contain two carbon atoms or fewer, show a way to prepare a racemic mixture of (2R, 3S) - and (2S, 3R) -2, 3-dihydroxypentane.
Predict the major product(s) for each of the following reactions:a.b.c.d. На На (PPH3)3RHCI H;o*
Paclitaxel (marketed under the trade name TaxolTM) is found in the bark of the Pacific yew tree, Taxus berevifolia, and is used in the treatment of cancer:(a) Draw the enantiomer of paclitaxel.(b) How many chirality centers does this compound possess? ОН .н Он ОН ищО
For each pair of compounds below, identify the more acidic compound:(a)(b)(c)(d)(e)(f)(g)(h) ОН SH ОН Он
Using any compounds that contain two carbon atoms or fewer, show a way to prepare a racemic mixture of (2R, 3R)- 2,3-dihydroxypentane and (2S,3S)-2,3-dihydroxypentane.
Propose a mechanism for each of the following transformations:a.b. Он H;0* Br HBr
Consider the following substitution reaction:(a) Determine whether this reaction proceeds via an SN1 or SN2 process.(b) Draw the mechanism of this reaction.(c) What is the rate equation of this reaction?(d) Would the reaction occur at a faster rate if sodium bromide were added to the reaction
Consider the following reaction:This reaction has been determined to be second order.(a) What is the rate equation for this reaction?(b) How will the rate be affected if the concentration of hydroxide is tripled?(c) How will the rate be affected if the concentration of chloroethane is tripled?(d)
In each group of compounds below, select the most acidic compound:(a)(b) Zーエ Zーエ CI CI CI
Propose a plausible synthesis for each of the following transformations:a.b.
Propose a mechanism for the following transformation: ОН [H,SO,] Меон Meo
Consider the following tetra-substituted cyclohexane:(a) Draw both chair conformations of this compound.(b) Determine which conformation is more stable.(c) At equilibrium, would you expect the compound to spend more than 95% of its time in the more stable chair conformation? ОН CI
Suggest an efficient synthesis for the following transformation: OH

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