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organic chemistry

Organic Chemistry 1st edition David R. Klein - Solutions

Coniine has molecular formula C8H17N and was present in the hemlock extract used to execute the Greek philosopher Socrates. Subjecting coniine to a Hofmann elimination produces (S)-N,N dimethyloct-7-en-4-amine. Coniine exhibits one peak above 3000 cm−1 in its IR spectrum. Draw the structure of
Piperazine is an antihelminthic agent (a drug used in the treatment of intestinal worms) that has molecular formula C4H10N2. The proton NMR spectrum of piperazine exhibits two signals. When dissolved in D2O, one of these signals vanishes over time. Propose a structure for piperazine.
Primary or secondary amines will attack epoxides in a ring-opening process:For substituted epoxides, nucleophilic attack generally takes place at the less sterically hindered side of the epoxide. Using this type of reaction, show how you might prepare the following compound from benzene, ammonia,
Phenacetin was widely used as an analgesic before it was removed from the market in 1983 on suspicion of being a carcinogen. It was widely replaced with acetaminophen (Tylenol), which is very similar in structure but is not carcinogenic. Starting with benzene and using any other reagents of your
Propose a mechanism for the following process: REN heat + N2 + CO2
Draw the structure of the compound with molecular formula C6H15N that exhibits the following1H NMR and13C NMR spectra: 3 Proton NMR 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 0.4 Chemical Shift (ppm) Carbon NMR -45.8 -11.3 40 10 50 70 80 30 20 Chemical Shift (ppm) 2.
Draw the structure of the compound with molecular formula C8H11N that exhibits the following1H NMR and13C NMR spectra: Proton NMR 2 22 Chemical Shift (ppm) Carbon NMR 128.8 128.4 40.0 -126.1 43.5- 138.8 120 50 40 140 130 110 100 90 80 70 60 Chemical Shift (ppm)
Using benzene as your only source of carbon atoms and ammonia as your only source of nitrogen atoms, propose a synthesis for the following compound: HN NH
Propose a synthesis for the following transformation: 'N'
When 3-methyl-3-phenyl-1-butanamine is treated with sodium nitrite and HCl, a mixture of products is obtained. The following compound was found to be present in the reaction mixture. Account for its formation with a complete mechanism (make sure to show the mechanism of formation for a nitrosonium
Guanidine is a neutral compound but is an extremely powerful base. In fact, it is almost as strong a base as a hydroxide ion. Identify which nitrogen atom in guanidine is so basic, and explain why guanidine is a much stronger base than most other amines. NH H,N NH2 Guanidine
Propose an efficient synthesis for each of the following compounds using the acetoacetic ester synthesis.(a)(b)(c)(d)
In Problem 22.38, we saw an intramolecular example of a malonic ester synthesis using excess base and 1,4-dibromobutane. If this dibromide is used in an acetoacetic ester synthesis, an intramolecular process can also occur. Predict the product of that reaction.
Draw a mechanism for the following transformation: 'CI フーエエーZ エーZ
When the following compound is treated with excess methyl iodide, a quaternary ammonium salt is obtained that bears only one positive charge. Draw the structure of the quaternary ammonium salt. Н *NH2
Draw the structures of all isomeric amines with molecular formula C6H15N that are not expected to produce any signal above 3000 cm−1 in their IR spectra.
Clomipramine is marketed under the trade name Anafranil and is used in the treatment of obsessive compulsive disorder.(a) Identify which nitrogen atom in clomipramine is more basic, and justify your choice.(b) Draw the form of clomipramine that is expected to predominate at physiological pH. N. N'
Spermine is a naturally occurring compound that contributes to the characteristic odor of semen. Classify each nitrogen atom in spermine as primary, secondary, or tertiary. Н NH2 H,N 'N' Н Spermine
How would you use NMR spectroscopy to distinguish between the following pairs of compounds?(a)(b) 'N. 'N- N.
Starting with benzene and any reagents with three or fewer carbon atoms, show how you would prepare each of the following compounds:(a)(b)(c)(d) Zエ NH2 CI .CI ČI
Draw the expected product of the following reductive amination: [H,SO,] NABH,CN `NH2
Meta-Bromoaniline was treated with NaNO2 and HCl to yield a diazonium salt. Draw the product obtained when that diazonium salt is treated with each of the following reagents:(a) H2O (b) HBF4 (c) CuCN (d) H3PO2 (e) CuBr
Predict the major product(s) for each of the following reactions:(a)(b)(c)(d) NO2 Fe Н,о Br NH2 [H*] NABH;CN
Draw the major product(s) that are expected when each of the following amines is treated with excess methyl iodide and then heated in the presence of aqueous silver oxide.(a)(b) NH2 NH2
Consider the structure of the azo dye called alizarine yellow R (below). Show the reagents you would use to prepare this compound via an azo coupling process. Он .N. N' Он O2N
Draw the product formed when each of the following compounds is treated with NaNO2and HCl:(a)(b) NH2 N.
Benzphetamine is an appetite suppressant that is marketed under the trade name Didrex and used in the treatment of obesity. Identify at least two different ways to make benzphetamine via a reductive amination process. `N' Benzphetamine
Rimantadine is an antiviral drug used to treat people infected with life-threatening influenza viruses. Identify the starting ketone that would be necessary in order to prepare rimantadine via a reductive amination. NH2 Rimantadine
In this chapter, we explained why pyrrole is such a weak base, but we did not discuss the acidity of pyrrole. In fact, pyrrole is 20 orders of magnitude more acidic than most simple amines. Draw the conjugate base of pyrrole and explain its relatively high acidity.
Fill in the missing reagents: .N СнО -NH2 СНо -NH2
Predict the major product for each of the following reactions,(a)(b)(c)(d) N- 1) Excess Mel 2) Ag,0, H,0, heat
One variation of the Gabriel synthesis employs hydrazine to free the amine in the final step of the synthesis. Draw the by-product obtained in this process. ? RNH, + N-R H,N-NH2
Draw a mechanism for the last step of the Gabriel synthesis, performed under basic conditions. .cooe NaOH RNH, N-R cooe
Propose a synthesis for each of the following transformations:(a)(b) N. -СООН
In general, nitrogen atoms are more basic than oxygen atoms. However, when an amide is treated with a strong acid, such as sulfuric acid, it is the oxygen atom of the amide that is protonated, rather than the nitrogen atom. Explain this observation.
Methadone is a powerful analgesic that is used to suppress withdrawal symptoms in the rehabilitation of heroin addicts. Identify the major product that is obtained when methadone is subjected to a Hofmann elimination. -N- Methadone
Para-Nitroaniline is an order of magnitude less basic than meta-nitroaniline.(a) Explain the observed difference in basicity.(b) Would you expect the basicity of ortho-nitroaniline to be closer in value to meta-nitroaniline or to para-nitroaniline?
When aniline is treated with fuming sulfuric acid, an electrophilic aromatic substitution reaction takes place at the meta position instead of the para position, despite the fact that the amino group is an ortho-para director. Explain this curious result. NH2 NH2 Fuming H,SO, So,H
Propose a mechanism for the following transformation: [н'] NABH,CN + NH3 CH;NH2 Н
Lidocaine is one of the most widely used local anesthetics. Draw the form of lidocaine that is expected to predominate at physiological pH. 'N. H. Lidocaine
Tertiary amines with three different alkyl groups are chiral but cannot be resolved because pyramidal inversion causes racemization at room temperature. Nevertheless, chiral aziridines can be resolved and stored at room temperature.Aziridine is a three-membered heterocycle containing a nitrogen
Identify how you would make hexylamine from each of the following compounds:(a) 1-Bromohexane(b) 1-Bromopentane(c) Hexanoic acid(d) 1-Cyanopentane
Identify how you would make each of the following compounds from 1-hexanol:(a) Hexylamine (b) Heptylamine (c) Pentylamine
Draw the structure of the major product obtained when aniline is treated with each of the following reagents:(a) Excess Br2(b) PhCH2COCl, py(c) Excess methyl iodide(d) NaNO2 and HCl followed by H3PO2(e) NaNO2 and HCl followed by CuCN
Each pair of compounds below will undergo an acidbase reaction. In each case, identify the acid, identify the base, draw curved arrows that show the transfer of a proton, and draw the products.(a)(b) ОН `N' N. HO,
Draw all tertiary amines with molecular formula C5H13N, and provide a name for each isomer. Are any of these compounds chiral?
Draw all constitutional isomers with molecular formula C4H11N, and provide a name for each isomer.
Assign a name for each of the following compounds:(a)(b)(c)(d)(e)(f) `NH2 ▪NH2
Identify the number of chirality centers in each of the following compounds:(a)(b)(c) `NH2 N'
Consider the structure of lysergic acid diethylamide (LSD), a potent hallucinogen containing three nitrogen atoms. One of these three nitrogen atoms is significantly more basic than the other two. Identify the most basic nitrogen atom in LSD, and explain your choice. Н LSD
Draw the structure of each of the following compounds:(a) N-Ethyl-N-isopropylaniline(b) N,N-Dimethylcyclopropylamine(c) (2R,3S)-3-(N,N-Dimethylamino)-2-pentanamine(d) Benzylamine
For each pair of compounds, identify the stronger base.(a)(b)(c) vs. N. N. z. Vs. %3D N. N.
Cinchocaine is a long-acting local anesthetic used in spinal anesthesia. Identify the most basic nitrogen atom in cinchocaine. Н N. N. Cinchocaine
Starting with sodium azide as your source of nitrogen and using any other reagents of your choice, show how you would prepare each of the compounds in Problem 23.18.Compounds in 23.18(a)(b)(c)(d)(e)(f) -NH2
Draw the structure of each of the following compounds:(a) Cyclohexylmethylamine(b) Tricyclobutylamine(c) 2,4-Diethylaniline(d) (1R,2S)-2-Methylcyclohexanamine(e) ortho-Aminobenzaldehyde
Predict the product obtained when pyrrole is treated with a mixture of nitric acid and sulfuric acid at 0ºC.
Pyridine undergoes electrophilic aromatic substitution at the C3 position. Justify this regiochemical outcome by drawing resonance structures of the intermediate produced from attack at C2, at C3, and at C4.
Draw the product obtained when the diazonium salt formed from aniline is treated with each of the following compounds:(a) Aniline(b) Phenol(c) Anisole (methoxybenzene)
Starting with benzene and isopropyl chloride, show how you would prepare the following compound: N- -NH2 O,N-
Identify the reactants you would use to prepare each of the following azo dyes via an azo coupling reaction:(a)(b)(c) N- !i -NH2 но S SO,H -NO2 Но
Propose an efficient synthesis for each of the following transformations:(a)(b)(c)(d)(e)(f) -NH2 CN NO2 Br Br
Predict the major product obtained when each of the following amines is treated with a mixture of NaNO2and HCl:(a)(b)(c)(d) NH2 エZ
Phencyclidine (PCP) was originally developed as an anesthetic for animals, but it has since become an illegal street drug because it is a powerful hallucinogen. Treatment of PCP with excess methyl iodide followed by aqueous silver oxide gives the following three principal products. Draw the
Compound A is an amine that does not possess a chirality center. Compound A was treated with excess methyl iodide and then heated in the presence of aqueous silver oxide to produce an alkene. The alkene was further subjected to ozonolysis to produce butanal and pentanal. Draw the structure of
Propose a synthesis for the following transformation (be sure to count the carbon atoms): Br
Draw the major product that is expected when each of the following compounds is treated with excess methyl iodide followed by aqueous silver oxide and heat:(a) Cyclohexylamine(b) (R)-3-Methyl-2-butanamine(c) N,N-Dimethyl-1-phenylpropan-2-amine
Using acetic acid as your only source of carbon atoms, show how you could make N-ethyl acetamide. Но,
Starting with nitrobenzene and using any other reagents of your choice, outline a synthesis of para-chloroaniline.
When aniline is treated with a mixture of nitric acid and sulfuric acid, the expected nitration product (para-nitroaniline) is obtained in poor yield. Instead, the major product from nitration is meta-nitroaniline. Apparently, the amino group is protonated under these acidic conditions, and the
Show the reagents you would use to achieve the following transformation: N. H.
Starting with potassium phthalimide as your source of nitrogen and using any other reagents of your choice, show how you would prepare each of the compounds in Problem 23.18.Compounds in 23.18(a)(b)(c)(d)(e)(f) -NH2
Using ammonia as your source of nitrogen, show the reagents you would use to prepare each of the following amines:(a)(b)(c)(d)(e)(f) Zエ
Propose an efficient synthesis for the following transformation: N.
Tri-tert-butylamine cannot be prepared via a reductive amination. Explain.
Methamphetamine is used in some formulations for the treatment of attention deficit disorder and can be prepared by reductive amination using phenylacetone and methylamine. Draw the structure of methamphetamine.
Show two different ways of preparing each of the following compounds via a reductive amination:(a)(b)(c)(d)(e) Zエ
Using a Gabriel synthesis, propose an efficient synthesis for each of the following transformations. In each case, you will need to use reactions from previous chapters to convert the starting material into a suitable alkyl halide that can be used in a Gabriel synthesis.(a)(b) -NH2 NH2 Он
Using a Gabriel synthesis, show how you would make each of the following compounds:(a)(b)(c)(d) `NH2 NH,
The following compound cannot be prepared from an alkyl halide or a carboxylic acid using the methods described in this section. Explain why each synthesis cannot be performed. `NH2
Draw the structure of an alkyl halide or carboxylic acid that might serve as a precursor in the preparation of each of the following amines:(a)(b)(c) `NH2 NH2
For each of the following compounds, draw the form that predominates at physiological pH:(a)(b)(c) Н CI CHз CI Sertraline (Zoloft) An antidepressant NH2 Amantadine Used in the treatment of Parkinson's disease
When (E)-4-amino-3-buten-2-one is treated with molecular hydrogen in the presence of platinum, the resulting amine is more basic than the reactant. Draw the reactant and the product, and explain why the product is a stronger base than the reactant.
Rank the following compounds in terms of increasing basicity: N. Br z-
For each of the following pairs of compounds, identify which compound is the stronger base:(a)(b)(c)(d) N- N- N- N-
Identify whether each of the following compounds is expected to be water soluble:(a)(b)(c) -NH2 -NH2
Rank this group of compounds in order of increasing boiling point. н -NH2 -N-
Draw all constitutional isomers with molecular formula C3H9N, and provide a name for each isomer.
Assign a name for each of the following compounds:(a)(b)(c)(d)(e)(f) NH
The following transformation cannot be accomplished by direct alkylation of an enolate. Explain why not, and then devise an alternate synthesis for this transformation.
This chapter covered many C-C bond-forming reactions, including aldol reactions, Claisen condensations, and Michael addition reactions. Two or more of these reactions are often performed sequentially, providing a great deal of versatility and complexity in the type of structures that can be
Propose a plausible mechanism for the following transformation. NaOH, H20 Heat
Propose a plausible mechanism for the following transformation. ОН ОН Ph H,O* Ph
Consider the structures of the constitutional isomers, Compound A and Compound B (below). When treated with aqueous acid, Compound A undergoes isomerization to give a cis stereoisomer. In contrast, Compound B does not undergo isomerization when treated with the same conditions. That is, Compound B
Predict the major product of the following transformation. CO2ET Нао C10H100 Heat
Lactones can be prepared from diethyl malonate and epoxides. Diethyl malonate is treated with a base, followed by an epoxide, followed by heating in aqueous acid:Using this process, identify what reagents you would need to prepare the following compound: 1) NaOEt EtO EtO OEt 2) OEt Н,о Heat
Draw the structure of the product with molecular formula C10H10O that is obtained when the compound below is heated with aqueous acid. CN CN Но C10H100 Heat
Acrolein is an Î±,Î²-unsaturated aldehyde that is used in the production of a variety of polymers. Acrolein can be prepared by treating glycerol with an acid catalyst. Propose a plausible mechanism for this transformation. ОН НО. H2SO, но TH. Heat Acrolein Glycerol
For a pair of keto-enol tautomers, explain how IR spectroscopy might be used to identify whether the equilibrium favors the ketone or the enol.
Propose an efficient synthesis for the following transformation.
Draw a plausible mechanism for the following transformation. NO2 NO2 NaOH, H,0 Нeat

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