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organic chemistry

Organic Chemistry structure and function 6th edition K. Peter C. Vollhardt, Neil E. Schore - Solutions

The following mixed Claisen condensation works best when one of the starting materials is present in large excess. Which of the two starting materials should be present in excess? Why? What side reaction will compete if the reagents are present in comparable amounts? NaOCH,, CH,OH CH;CH,COCH,
Give the expected results of the reaction of each of the following molecules (or combinations of molecules) with excess NaOCH2CH3 in CH3CH2OH, followed by aqueous acidic work-up. (a)(b)(c)(d)(e)(f)(g)(h)(i) CH;CH,CH,COOCH,CH;
Arrange the following compounds in order of increasing acidity. Estimate pKa values for each. (a)(b) CH3CO2H(c) CH3OH (d)(e) CH3CHO (f)(g) CH3O2CCH2CO2CH3(h) CH3O2CCO2CH3 СОСН
Examination of the 1H NMR spectra of the following three isomeric nitrophenols reveals that one of them displays a hydroxy (phenolic) proton at substantially lower field than do the other two. Which one? (a)(b)(c) HO NO2
What is the principal product after the slurry obtained on treating benzenamine (aniline) with potassium nitrite and HCl at 0°C has been added to 4-ethylphenol?(a)(b)(c)(d) ОН N=NC,Hs CH,CH3
The transformation of 4-methylbenzenediazonium bromide to toluene is best carried out by using: (a) H+, H2O (b) H3PO2, H2O (c) H2O, -OH (d) Zn, NaOH
What are the products of the following reaction? (a) C6H5I + CH3OH (b) C6H5OH + CH3I (c) C6H5I + CH3I (d) CH;OCH, HL A, HI. A, ?
After chlorobenzene has been boiled in water for 2 h, which of the following organic compounds will be present in greatest concentration? (a) C6H5OH (b)(c)(d) C6H5Cl(e) Cl HO
As a team, consider the following schemes that outline steps toward the total synthesis of taxodone D, a potential anticancer agent. For the first scheme, divide your team into two groups, one to discuss the best option for A to effect the initial reduction step, the second to assign a structure to
Is the site of reaction in the biosynthesis of norepinephrine from dopamine (see Chapter 5, Problem 65) consistent with the principles outlined in this chapter? Would it be easier or more diffi cult to duplicate this transformation nonenzymatically? Explain. Chapter 5 Problem 65 НО н НО.
The urushiols are the irritants in poison ivy and poison oak that give you rashes and make you itch upon exposure. Use the following information to determine the structures of urushiols I (C21H36O2) and II (C21H34O2), the two major members of this family of unpleasant compounds.
(a) Give the key reaction that illustrates the inhibition of fat oxidation by the preservative BHT. (b) The extent to which fat is oxidized in the body can be determined by measuring the amount of pentane exhaled in the breath. Increasing the amount of vitamin E in the diet decreases the
Show the reagents that would be necessary for the synthesis by diazo coupling of each of the following three compounds. (a) Methyl Orange(b) Congo Red (c) -SO,NH2 Prontosil, H2N- which is NH2 converted microbially into sulfanilamide, H,N- -SO,NH2
Write the most reasonable structure of the product of each of the following reaction sequences. (a)(b)For the following reaction, assume that electrophilic substitution occurs preferentially on the most activated ring. (c) I. NANO, HCI, 5°C NH2 OH 2. HO Golden Yellow SO,H
Devise a synthesis of each of the following substituted benzene derivatives, starting from benzene. (a)(b)(c)(d)(e)(f)(g) Br
Show how you would convert 3-methylbenzenamine into each of the following compounds: (a) methylbenzene; (b) 1-bromo-3-methylbenzene; (c) 3-methylphenol; (d) 3-methylbenzonitrile; (e) N-ethyl-3-methylbenzenamine.
Formulate a detailed mechanism for the diazotization of benzenamine (aniline) in the presence of HCl and NaNO2. Then suggest a plausible mechanism for its subsequent conversion into iodobenzene by treatment with aqueous iodide ion (e.g., from K+I-).
As mentioned in Section 22-10, the Sandmeyer reactions, in which copper(I) ion catalyzes substitution of the nitrogen in arenediazonium salts by Cl, Br, or CN, take place by complex mechanisms involving radicals. Explain why these substitutions do not follow either the SN1 or SN2
A common application of the Cope rearrangement is in ring-enlargement sequences. Fill in the reagents and products missing from the following scheme, which illustrates the construction of a 10-membered ring. 1. LIAIH, (CH,CH,).O 2. H, Н.О (а) Excess PCC, CH,CI, 200°C (e) (d)
Biochemical oxidation of aromatic rings is catalyzed by a group of liver enzymes called aryl hydroxylases. Part of this chemical process is the conversion of toxic aromatic hydrocarbons such as benzene into water-soluble phenols, which can be easily excreted. However, the primary purpose of the
Chili peppers contain significant quantities of vitamins A, C, and E, as well as folic acid and potassium. They also contain small quantities of capsaicin, the fiery essence responsible for the “hot” in hot peppers. The pure substance is in fact quite dangerous: Chemists working with capsaicin
As a children’s medicine, acetaminophen (Tylenol) has a major marketing advantage over aspirin: Liquid Tylenol preparations (essentially, acetaminophen dissolved in fl avored water) are stable, whereas comparable aspirin solutions are not. Explain.
Give the expected product(s) of each of the following reaction sequences. (a)(b)(c)(d)(e)(e) ОН 1.2 CН—СНСH, Br, NaOH 2. Д ОН
Name each of the following compounds. (a)(b)(c)(d)(e) OH ОН Cl, Br
Starting with benzene, propose syntheses of each of the following phenol derivatives. (a)(b)(c) ОСН-СООН CI Ci The herbicide 2,4-D
Design a synthesis of each of the following phenols, starting with either benzene or any monosubstituted benzene derivative. (a)(b)(c) The three benzenediols(d) ОН ČH3
Rank the following compounds in order of descending acidity. (a) CH3OH(b) CH3COOH(c)(d)(e)(f) OH ŠO,H
Give the expected major product(s) of each of the following reactions and reaction sequences. (a)(b)(c) 1. KMNO,. -OH, A 2. H*, H,O
The reaction sequence shown below illustrates the synthesis of 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), a powerful herbicide. A 1 : 1 mixture of the butyl esters of 2,4,5-T and its dichlorinated analog 2,4-D was used between 1965 and 1970 as a defoliant during the Vietnam War under the code
A very efficient short synthesis of resveratrol was reported in 2006. Fill in reasonable reagents for steps (a) through (d). Refer to the referenced text sections as needed. CH,CO, HO HO (a) (b) -СНО -CH=CH2 CH=CH, Section Sections 17-12 19-9, 20-3 НО НО CH;CO CH;CO (c) (d) -CH=CH-
Give the likely products of each of the following reactions. Each one is carried out in the presence of a Pd catalyst, a phosphine, and heat. (a)(b)(c)(d) F;C- Cl 'N' H
Based on the mechanism presented for the Pd-catalyzed reaction of a halobenzene with hydroxide ion, write out a reasonable mechanism for the Pd-catalyzed reaction of 1-bromo-3-methoxybenzene with 2-methyl-1-propanamine.
In nucleophilic aromatic substitution reactions that proceed by the addition – elimination mechanism, fluorine is the most easily replaced halogen in spite of the fact that F- is by far the worst leaving group among halide ions. For example, 1-fluoro-2,4-dinitrobenzene reacts much more rapidly
Explain the mechanism of the following synthetic transformation. ỌCH3 OCH3 1. CH,CH,CH,CH,Li F 2. H.C=0 3. Н, Н.О CH,OH CH2CH,CH,CH3
Starting with benzenamine, propose a synthesis of aklomide, an agent used to treat certain exotic fungal and protozoal infections in veterinary medicine. Several intermediates are shown to give you the general route. Fill in the blanks that remain; each requires as many as three sequential
Predict the main product(s) of the following reactions. In each case, describe the mechanism(s) in operation. (a)(b)(c) CI NO2 H,NNH, NO2
Rank the following compounds in descending order of reactivity toward hydroxide ion. Br Br Br Br Br NO2 NO2 `NO2 `NO2 ÑO2 ÑO2 ÑO2
Outline a straightforward, practical, and efficient synthesis of each of the following compounds. Start with benzene or methylbenzene. Assume that the para isomer (but not the ortho isomer) may be separated efficiently from any mixtures of ortho and para substitution products. (a)(b)(c)(d)
The hydrocarbon with the common name fluorene is acidic enough (pKa ≈ 23) to be a useful indicator in deprotonation reactions of compounds of greater acidity. Indicate the most acidic hydrogen(s) in fl uorene. Draw resonance structures to explain the relative stability of its conjugate
Give the expected products of the following reactions or reaction sequences. (a)(b)(c) H,O, A BГCH-CH,CH> CH,Br
Triphenylmethyl radical, (C6H5)3C•, is stable at room temperature in dilute solution in an inert solvent, and salts of triphenylmethyl cation, (C6H5)3C+, can be isolated as stable crystalline solids. Propose explanations for the unusual stabilities of these species.
By drawing appropriate resonance structures, illustrate why halogen atom attachment at the para position of phenylmethyl (benzyl) radical is unfavored compared with attachment at the benzylic position.
Predict the order of relative stability of the three benzylic cations derived from chloromethylbenzene (benzyl chloride), 1-(chloromethyl)-4-methoxybenzene (4-methoxybenzyl chloride), and 1-(chloromethyl)-4-nitrobenzene (4-nitrobenzyl chloride). Rationalize your answer with the help of resonance
Propose syntheses of each of the following compounds, beginning in each case with ethylbenzene. (a) (1-Chloroethyl)benzene; (b) 2-phenylpropanoic acid; (c) 2-phenylethanol; (d) 2-phenyloxacyclopropane.
Formulate a mechanism for the reaction described in Problem 35(b). Problem 35(b)(b) NBS (1 equivalent), hv
Give the expected major product(s) of each of the following reactions. (a)(b) CH,CH3 CI.(1 equivalent), hv
Use the following partial IR- and mass-spectral data to identify one of the structures among the selection given. IR spectrum: 3300 and 1690 cm-1; mass spectrum: m/z = 73 (parent ion). (a)(b)(c)(d)(e) HCN(CH3)2
Which of the following formulas best represents diazomethane? (a)(b)(c)(d)(e) CH,=N=N:
Rank the basicities of the following three nitrogen-containing compounds (most basic first): A: NH3 B: CH3NH2 C: (CH3)4N+ NO3-(a) A > B > C; (b) B > C > A; (c) C > A > B; (d) C > B > A; (e) B > A > C.
Identify the best conditions for the following transformation: (a) H2, metal catalyst; (b) excess CH3I, K2CO3; (c) Br2, NaOH, H2O; (d) LiAlH4, ether; (e) CH2N2, ether. CH;CH,CNH, CH;CH,NH, + CO2
One of the following four amines is tertiary. Which one? (a) Propanamine; (b) N-methylethanamine; (c) N,N-dimethylmethanamine;(d) N-methylpropanamine.
Quaternary ammonium salts catalyze reactions between species dissolved in two immiscible phases, a phenomenon called phase-transfer catalysis. For example, heating a mixture of 1-chlorooctane dissolved in decane with aqueous sodium cyanide shows no sign of the SN2 product, nonanenitrile. On the
Many alkaloids are synthesized in nature from a precursor molecule called norlaudanosoline, which in turn appears to be derived from the condensation of amine A with aldehyde B. Formulate a mechanism for this transformation. Note that a carbon – carbon bond is formed in the process. Name a
Skytanthine is a monoterpene alkaloid with the following properties. Analysis: C11H21N. 1H NMR: two CH3 doublets (J = 7 Hz) at δ = 1.20 and 1.33 ppm; one CH3 singlet at δ = 2.32 ppm; other hydrogens give rise to broad signals at δ = 1.3 – 2.7 ppm. IR: no bands ≥ 3100 cm-1. Deduce the
Pethidine, the active ingredient in the narcotic analgesic Demerol, was subjected to two successive exhaustive methylations with Hofmann eliminations, and then ozonolysis, with the following results: (a) Propose a structure for pethidine based on this information. (b) Propose a synthesis
From the following information, deduce the structure of coniine, a toxic amine found in poison hemlock, which, deservedly, has a very bad reputation. IR: 3330 cm-1. 1H NMR: δ = 0.91 (t, J = 7 Hz, 3 H), 1.33 (s, 1 H), 1.52 (m, 10 H), 2.70 (t, J = 6 Hz, 2 H), and 3.0 (m, 1 H) ppm. Mass spectrum: m/z
Several of the natural amino acids are synthesized from 2-oxocarboxylic acids by an enzymecatalyzed reaction with a special coenzyme called pyridoxamine. Use electron-pushing arrows to describe each step in the following synthesis of phenylalanine from phenylpyruvic acid. CO.H CH,NH, CH,N=C
Reductive amination of excess formaldehyde with a primary amine leads to the formation of a dimethylated tertiary amine as the product (see the following example). Propose an explanation. NABH,CN, CH,OH (CH3),CCH,NH, + 2 CH,=0 (CH3),CCH,N(CH;), 84% 2,2-Dimethylpropanamine
Reductive amination of excess formaldehyde with a primary amine leads to the formation of a dimethylated tertiary amine as the product (see the following example). Propose an explanation. NABH,CN, CH,OH (CH3),CCH,NH, + 2 CH,=0 (CH3),CCH,N(CH3), 84% 2,2-Dimethylpropanamine
Reductive amination of excess formaldehyde with a primary amine leads to the formation of a dimethylated tertiary amine as the product (see the following example). Propose an explanation. NABH,CN, CH,OH (CH3),CCH,NH, + 2 CH,=0 (CH3),CCH,N(CH3), 84% 2,2-Dimethylpropanamine
Tertiary amines undergo reversible conjugate addition to a,b-unsaturated ketones (see Chapter 18). This process is the basis for the Baylis-Hillman reaction, which is catalyzed by tertiary amines, that resembles a crossed aldol reaction. An example is shown below. (a) Formulate a mechanism for
Tertiary amines add readily as nucleophiles to carbonyl compounds, but, lacking a hydrogen on nitrogen, they cannot deprotonate to give a stable product. Instead, their addition gives an intermediate that is highly reactive toward other nucleophiles. Thus, tertiary amines are occasionally used as
Give the expected product(s) of each of the following reactions. (a)(b) H;C NH2 CH NaNO,, HCI, H,O
Illustrate a method for achieving the transformation shown in the margin, using combinations of reactions presented in Sections 21-8 and 21-9. Section 21-8Section 21-9 Hofmann Elimination of 1-Butanamine CH;CH,CH,CH,NH, Excess CH,I, K,CO, H,0 CH;CH,CH,CHN(CH;)3 I- Ag.0, H,O 1-Butanamine -AgI
Tropinone (Problem 48) was first synthesized by Sir Robert Robinson, in 1917, by the following reaction. Show a mechanism for this transformation. Problem 48 H3C H H3C H,C + CH;NH, + C=0 H,C. H;C H
Show how each of the following molecules might be synthesized by Mannich or Mannich-like reactions. (a)(b)(c)(d)(e) N(CH3)2 =0
Attempted Hofmann elimination of an amine containing a hydroxy group on the b-carbon gives an oxacyclopropane product instead of an alkene. (a) Propose a sensible mechanism for this transformation. (b) Pseudoephedrine (see Problem 42) and ephedrine are closely related, naturally occurring
Reaction of the tertiary amine tropinone with (bromomethyl)benzene (benzyl bromide) gives not one but two quaternary ammonium salts, A and B. Compounds A and B are stereoisomers that are interconverted by base; that is, base treatment of either pure isomer leads to an equilibrium mixture of
Formulate a detailed mechanism for the Mannich reaction between 2-methylpropanal, formaldehyde, and methanamine shown on page 994. Page 994 Mannich Reaction CH,N(CH,), Cl- 1. H HCI, CH,CH,OH, A + CH2=0 + (CH3)2NH 85% Ketone More reactive Amine Salt of Mannich base aldehyde CH3 CH3 1. HCI,
What primary amine(s) would give each of the following alkenes or alkene mixtures upon Hofmann elimination? (a) 3-Heptene; (b) mixture of 2- and 3-heptene; (c) 1-heptene;(d) mixture of 1- and 2-heptene.
Give the structures of the possible alkene products of Hofmann elimination of each of the following amines. If a compound can be cycled through multiple eliminations, give the products of each cycle. (a)(b)(c)(d)(e) NH2 -CHCH,CH3
Suggest the best syntheses that you can for the following amines, beginning each with any organic compounds that do not contain nitrogen. (a) Butanamine; (b) N-methylbutanamine; (c) N,Ndimethylbutanamine.
Apetinil, an appetite suppressant, has the structure shown in the margin. Is it a primary, a secondary, or a tertiary amine? Propose an effi cient synthesis of Apetinil from each of the following starting materials. Try to use a variety of methods. (a) C6H5CH2COCH3 (b)(c) Br C,H;CH,CHCH3
Phenylpropanolamine (PPA) has long been an ingredient in many cold remedies and appetite suppressants. In late 2000, the FDA asked manufacturers to remove products containing this compound from the market because of evidence of an increased risk of hemorrhagic stroke. This action has caused a
Give the structures of all possible nitrogen-containing organic products that might be expected to form on reaction of chloroethane with ammonia.
For each synthesis in Problem 39 that does not work well, propose an alternative synthesis of the final amine, starting either with the same material or with a material of similar structure and functionality. Data From Problem 39(a)(b)(c)(d)(e)(f)(g)(h)(i)(j) 1. KCN, CH,CH,ОН 2. LIAIH,
The following syntheses are proposed for amines. In each case, indicate whether the synthesis will work well, poorly, or not at all. If a synthesis will not work well, explain why (a)(b)(c)(d)(e)(f)(g)(h)(i)(j) 1. KCN, CH,CH,ОН 2. LIAIH, (CH,CH,),O CH;CH2CH,CH,CI → CH;CH,CH,CH,NH2
Without consulting the Reaction Road Map on page 1009, suggest reagents that convert each of the following starting materials into the indicated product: (a) (chloromethyl)- benzene (benzyl chloride) into phenylmethanamine (benzylamine); (b) benzaldehyde into phenylmethanamine
Several functional groups containing nitrogen are considerably stronger bases than are ordinary amines. One is the amidine group found in DBN and DBU, both of which are widely used as bases in a variety of organic reactions. Another unusually strong organic base is guanidine, . Indicate
How would you expect the following classes of compounds to compare with simple primary amines as bases and acids?(a) Carboxylic amides; for example, CH3CONH2 (b) Imides; for example, CH3CONHCOCH3 (c) Enamines; for example, CH2PCHN(CH3)2(d) Benzenamines; for example, -NH2
In which direction would you expect each of the following equilibria to lie? (a) NH3 + -OH ⇌ NH2- + H2O (b) CH3NH2 + H2O ⇌ CH3NH3+ + -OH (c) CH3NH2 + (CH3)3NH+ ⇌ CH3NH3+ + (CH3)3N
Is a molecule whose conjugate acid has a high pKa value a stronger or a weaker base than a molecule whose conjugate acid has a low pKa value? Explain using a general equilibrium equation.
The following mass-spectral data are for two of the compounds in Problem 32. Match each mass spectrum with one of them. (a) m/z (relative intensity) = 101(8), 86(11), 72(79), 58(10), 44(40), and 30(100). (b) m/z (relative intensity) = 101(3), 86(30), 58(14), and 44(100).Data From Problem
The following spectroscopic data (13C NMR and IR) are for several isomeric amines of the formula C6H15N. Propose a structure for each compound. (a) 13C NMR: δ = 23.7 (CH3) and 45.3 (CH) ppm. IR: 3300 cm-1. (b) 13C NMR: δ = 12.6 (CH3) and 46.9 (CH2) ppm. IR: no bands in 3250 – 3500
Use the following NMR- and mass-spectral data to identify the structures of two unknown compounds, A and B. A: 1H NMR: δ = 0.92 (t, J = 6 Hz, 3 H), 1.32 (broad s, 12 H), 2.28 (broad s, 2 H), and 2.69 (t, J = 7 Hz, 2 H) ppm. Mass spectrum myz (relative intensity) 5 129(0.6) and 30(100). B: 1H
The inversion of nitrogen requires a change of hybridization. (a) What is the approximate energy difference between pyramidal nitrogen (sp3 hybridized) and trigonal planar nitrogen (sp2 hybridized) in ammonia and simple amines? (b) Compare the nitrogen atom in ammonia with the carbon atom
Name each of the following compounds pictured in Chemical Highlight 21-1 according to IUPAC or Chemical Abstracts. Pay attention to the order of precedence of the functional groups. (a) Propylhexedrine; (b) Amphetamine; (c) Mescaline; (d) Epinephrine.
Give structures that correspond to each of the following names. (a) N,N-Dimethyl-3-cyclohexenamine; (b) N-ethyl-2-phenylethylamine; (c) 2-aminoethanol; (d) m-chloroaniline.
Give at least two names for each of the following amines. (a)(b)(c)(d)(e) (CH3)3N(f)(g)(h) (CH3CH2)2NCH2CH=CH2 NH,
Formulate a mechanism for the reaction of methyl 9-octadecenoate with 1-dodecanamine shown on p. 939. Page 939 H. 230°C CH3(CH,),CH=CH(CH,),COCH; + CH3(CH,)1|NH (See Problem 43) Methyl 9-octadecenoate 1-Dodecanamine CH3(CH),CH=CH(CH,),ČNH(CH,)11CH3 + CH;OH 69% N-Dodecyl-9-octadecenamide
Formulate a mechanism for the acid-catalyzed transesterifi cation of ethyl 2-methylpropanoate (ethyl isobutyrate) into the corresponding methyl ester. Your mechanism should clearly illustrate the catalytic role of the proton.
Draw the structure of each of the following compounds: (a) β-butyrolactone; (b) β-valerolactone; (c) δ-valerolactone; (d) β-propiolactam; (e) α-methyl-d-valerolactam; (f) N-methyl-g-butyrolactam.
Give the products of reaction of γ-valerolactone (5-methyloxa-2-cyclopentanone,) with each of the reagents in Problem 39. Data From Problem 39(a) NaOH, H2O, heat; then H+, H2O (b) (CH3)2CHCH2CH2OH(excess), H+ (c) (CH3CH2)2NH, heat (d) CH3MgI(excess), (CH3CH2)2O; then H+,
Give the products of reaction of methyl pentanoate with each of the following reagents under the conditions shown. (a) NaOH, H2O, heat; then H+, H2O (b) (CH3)2CHCH2CH2OH(excess), H+ (c) (CH3CH2)2NH, heat (d) CH3MgI(excess), (CH3CH2)2O; then H+, H2O (e) LiAlH4, (CH3CH2)2O;
Which of the three compounds below would be the most reactive toward hydrolysis with aqueous base? (a)(b)(c) СОСH
The best description for compound A (see margin) is (a) An amide; (b) A lactam; (c) An ether; (d) A lactone. H2C-C H2C-O A
Saponification of with aqueous NaOH will give (a) (CH3)2CHCO2 -Na+ + CH3CH2CH2 18OH; (b)(c) (CH3)2CHOCH2CH2CH3 + C≡ 18O; (d) (CH3)2CHCHO + CH3CH2CH2 18OH. (CH3)2CHC18OCH2CH2CH3
What is the IUPAC name of the compound shown in the margin? (a) Isopropyl 2-fluoro3-methylbutanoate; (b) 2-fluoroisobutanoyl 2-propanoate; (c) 1-methylethyl 2-fluorobutyrate; (d) 2-fluoroisopropyl isopropanoate; (e) 1-methylethyl 2-fluoro-2-methylpropanoate. F
Friedel-Crafts acylations are best carried out with acyl halides, but other carboxylic acid derivatives undergo this process, too, such as carboxylic anhydrides or esters. These reagents may have some drawbacks, however, the subject of this problem. Before you start, discuss as a group the
Spectroscopic data for two carboxylic acid derivatives are given in NMR-A and NMR-B. Identify these compounds, which may contain C, H, O, N, Cl, and Br but no other elements. (a) 1H NMR: spectrum A (one signal has been amplified to reveal all peaks in the multiplet). IR: 1728 cm-1.

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