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organic chemistry
Organic Chemistry 1st edition David R. Klein - Solutions
Draw both resonance structures of the enolate formed when each of the following ketones is treated with a strong base:(a)(b)(c)(d)(e)
Draw the two possible enols that can be formed from 3-methyl-2-butanone, and show a mechanism of formation ofeach under base-catalyzed conditions.
Draw a mechanism for the reverse process of the previous problem. In other words, draw the acid-catalyzed conversion of 1-cyclohexenol to cyclohexanone.
Draw a mechanism for the acid-catalyzed conversion of cyclohexanone into its tautomeric enol.
Dimethylformamide (DMF) is a common solvent:(a) The 1H NMR spectrum of DMF exhibits three signals. Upon treatment with excess LAH followed by water, DMF is converted into a new compound that exhibits only one signal in its 1H NMR spectrum. Explain.(b) Based on your answer to part a, how many
N-Acetylazoles undergo hydrolysis more readily than regular amides. Suggest a reason for the enhanced reactivity of N-acetylazoles toward nucleophilic acyl substitution: N: 'N- N-Acetylazole
Propose a mechanism for the following transformation, and explain how you could use an isotopic labeling experiment to verify your proposed mechanism: [H,SO,] Но НО R.
A compound with molecular formula C8H8O3exhibits the following IR,1H NMR and13C NMR spectra. Deduce the structure of this compound.
Describe how you could use NMR spectroscopy to distinguish between benzoyl chloride and para-chlorobenzaldehyde.
Describe how you could use IR spectroscopy to distinguish between ethyl acetate and butyric acid.
A compound with molecular formula C10H10O4 exhibits only two signals in its 1H NMR spectrum: a singlet at 4.0 (I = 3H) and a singlet at 8.1 (I = 2H). Identify the structure of this compound.
A carboxylic acid with molecular formula C5H10O2 is treated with thionyl chloride to give compound A. Compound A has only one signal in its 1H NMR spectrum. Draw the structure of the product that is formed when compound A is treated with excess ammonia.
Draw a plausible mechanism for the following transformation Н,о* ОН но
Starting with benzene and using any other reagents of your choice, devise a synthesis for acetaminophen: N. но НО Acetaminophen (TylenolTM)
Propose an efficient synthesis for each of the following transformations:(a)
Meta-Hydroxybenzoyl chloride is not a stable compound, and it polymerizes upon preparation. Show a mechanism for the polymerization of this hypothetical compound.
Identify what monomers you would use to produce the following polymer: Zーエ Zーエ Zーエ Zーエ
Draw the structure of the polymer produced when the following two monomers are allowed to react with each other: ОН CI CI но
DexonTM (below) is a polyester that is spun into fibers and used for surgical stitches that dissolve over time, eliminating the need for a follow-up procedure to remove the stitches. The ester moieties are slowly hydrolyzed by enzymes present in the body, and in this way, the stitches are dissolved
Pivampicillin is a penicillin prodrug:The prodrug ester moiety (in red) enables a more rapid delivery of the prodrug to the bloodstream, where the ester moiety is subsequently hydrolyzed by enzymes, releasing the active drug.(a) Draw the structure of the active drug.(b) What is the name of the
Draw the structure of the diol that is produced when the following carbonate is heated under aqueous acidic conditions.
Ethyl trichloroacetate is significantly more reactive toward hydrolysis than ethyl acetate. Explain this observation.
Draw a plausible mechanism for each of the following transformations:a.b.c.d.e. он Pyridine CI
Aspartame (below) is an artificial sweetener used in diet soft drinks and is marketed under many trade names, including EqualTMand NutrasweetTM. In the body, aspartame is hydrolyzed to produce methanol, aspartic acid, and phenylalanine. The production of phenylalanine poses a health risk to infants
Benzyl acetate is a pleasant-smelling ester found in the essential oil of jasmine flowers and is used in many perfume formulations. Starting with benzene and using any other reagents of your choice, design an efficient synthesis for benzyl acetate. Benzyl acetate
Fluphenazine is an antipsychotic drug that is administered as an ester prodrug via intramuscular injection:The hydrophobic tail of the ester is deliberately designed to enable a slow release of the prodrug into the bloodstream, where the prodrug is rapidly hydrolyzed to produce the active drug.(a)
Phosgene is highly toxic and was used as a chemical weapon in World War I. It is also a synthetic precursor used in the production of many plastics.(a) When vapors of phosgene are inhaled, the compound rapidly reacts with any nucleophilic sites present (OH groups, NH2 groups, etc.), producing HCl
When acetic acid is treated with isotopically labeled water (18O, shown in red) in the presence of a catalytic amount of acid, it is observed that the isotopic label becomes incorporated at both possible positions of acetic acid. Draw a mechanism that accounts for this observation. [н]. H20 ОН
Predict the products that are formed when diphenyl carbonate is treated with excess methyl magnesium bromide. 1) Excess MeMgBr 2) H3o*
DEET is the active ingredient in many insect repellants, such as OFFTM. Starting with meta-bromotoluene and using any other reagents of your choice, devise an efficient synthesis for DEET. .Br m-Bromotoluene N,N-Diethyl-m-toluamide (DEET)
Identify the reagents necessary to accomplish each of the following transformations: H. Он OR NH2
When methyl benzoate bears a substituent at the para position, the rate of hydrolysis of the ester moiety depends on the nature of the substituent at the para position. Apparently, a methoxy substituent renders the ester less reactive, while a nitro substituent renders the ester more reactive.
Propose an efficient synthesis for each of the following transformations:a.b.c.d. Br ОН
Starting with benzene and using any other reagents of your choice, show how you would prepare each of the following compounds:a.b.c.d. ОН
Identify the reagents you would use to convert 1-bromopentane into each of the following compounds:(a) Pentanoic acid(b) Hexanoic acid(c) Pentanoyl chloride(d) Hexanamide(e) Pentanamide(f) Ethyl hexanoate
Determine the structures of compounds A through F: ОН Na,Cr,0, H2SO4, H20 [H'] A EtOН soch 1) LIAI(OR)H `2) H20 xS NH3
Identify the carboxylic acid and the alcohol that are necessary in order to make each of the following compounds via a Fischer esterification:a.b.c. CH3CH2CO2C (CH3)3
In each case, identify the most likely position at which monobromination would occur.(a)(b)(c)(d) N.
Picric acid is a military explosive formed via the nitration of phenol under conditions that install three nitro groups. Draw the structure and provide an IUPAC name for picric acid.
When para-bromotoluene is treated with sodium amide, two products are obtained. Draw both products, and propose a plausible mechanism for their formation.
Each of the following syntheses will not produce the desired product. In each case, identify the flaw in the synthesis.(a)(b)(c)(d) NO2 1) HNO3, H2SO, 2) EECI, AICI3 Et Br 1) Br2, FeBrz 2) AICI,
Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds:(a)(b)(c) Br-
For each of the following groups, identify whether it is an activator or a deactivator, and determine its directing effects:(a)(b)(c)(d)(e)(f)(g)(h)(i)(j) -OMe
Predict the major product obtained when each of the following compounds is treated with fuming sulfuric acid:(a) Chlorobenzene(b) Phenol(c) Benzaldehyde(d) Ortho-Nitrophenol(e) Para-Bromotoluene(f) Benzoic acid(g) Para-Ethyltoluene(h) Benzene
Predict the product(s) obtained when each of the following compounds is treated with a mixture of nitric acid and sulfuric acid:(a)(b)(c)(d)(e) Br
Identify which of the following compounds is most activated toward electrophilic aromatic substitution. Which compound is least activated? Br „NO2 NO2 OMe но.
Rank the following compounds in order of increasing reactivity toward electrophilic aromatic substitution: Br Br- Br
Identify the reagents necessary to accomplish each of the following transformations: SO3H Br ZON СВiз „NH2 ОН
When ortho-bromonitrobenzene is treated with NaOH at elevated temperature, only one product is formed.(a) Draw the product.(b) Identify the intermediate formed en route to the product.(c) Would the reaction occur if the starting compound were meta-bromonitrobenzene?(d) Would the reaction occur if
When 2-ethyl-5-chlorotoluene was treated with sodium hydroxide at high temperature, followed by treatment with H3O+, three constitutional isomers with molecular formula C9H12O were obtained. Draw all three products.
Draw the most likely mechanism for each of the following transformations.(a)(b)(c) Br ОН 1) NaOH, heat 2) Н,о* Br Br2 FeBr3
Starting with benzene and using any other necessary reagents of your choice, design a synthesis for anisole (methoxybenzene).
Draw both products that are obtained when 4-chloro- 2-methyltoluene is treated with sodium amide followed by treatment with H3O+.
The presence of additional nitro groups can have an impact on the temperature at which a nucleophilic aromatic substitution will readily occur. Consider the following example.When both R groups are hydrogen atoms, the reaction readily occurs at 130°C. When one of the R groups is a nitro group,
Starting with benzene and using any other necessary reagents of your choice, design a synthesis for the following compound. -NH2 но-
Predict the product of the following reaction. Br NaOCH3, heat -NO2
The following compound has a pentasubstituted benzene ring.(a) Starting with benzene and using any other necessary reagents of your choice, design a synthesis for this compound.(b) It is very difficult to install a sixth substituent. Explain.(c) Is the ring activated or deactivated (relative to
Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible answer.(a)(b)(c)(d) Br. H,N. Br
The following compounds cannot be made using only reactions that we learned in this chapter. For each compound, explain the issues that prevent its formation:(a)(b) NH2 „NO2
Using only reactions that we learned in this chapter, there are two different ways to prepare the following compound from benzene. Identify both ways, and then determine which way is likely to produce a better yield of the desired product. Explain your choice.
Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. Some of the problems have more than one plausible answer.(a)(b)(c)(d)(e)(f)(g)(h)(i)(j) H2N Br O,N .CI
Identify the product obtained when benzene is treated with each of the following reagents:(a) Fuming sulfuric acid(b) HNO3 / H2SO4(c) Cl2, AlCl3(d) Ethyl chloride, AlCl3(e) Br2, Fe(f) HNO3 / H2SO4 followed by Zn, HCl
Identify the reagents necessary to convert benzene into each of the following compounds:(a) Chlorobenzene(b) Nitrobenzene(c) Bromobenzene(d) Ethylbenzene(e) Propylbenzene(f) Isopropylbenzene(g) Aniline (aminobenzene)(h) Benzoic acid(i) Toluene
The following transformations cannot be accomplished, even with the help of blocking groups. In each case, explain why a blocking group will not help.(a)(b) но он Но. но ОН Но NO2 Br
Predict the major product of the following reaction. H®OS Dilute H2SO. Но,5S. ŠO,H
Determine whether a blocking group is necessary to accomplish each of the following transformations.(a)(b)(c)(d) `NO2 Br
When the following compound is treated with Br2in the presence of a Lewis acid, one product predominates. Determine the structure of that product. Br FeBr3 ?
The following compound is highly activated, but nevertheless undergoes bromination very slowly. Explain.
For each of the following compounds, determine the position that is most likely to be the site of an electrophilic aromatic substitution reaction:(a)(b)(c)(d)(e) Но. NO2 O,N OMe Br
When 2,4-dibromo-3-methyltoluene is treated with bromine in the presence of iron (Fe), a compound with molecular formula C8H7Br3 is obtained. Identify the structure of this product.
Predict the product(s) for each of the following reactions:(a)(b)(c) OH HNO, H,SO, OMe Br Br2 FeBr3
For each compound below, identify which position(s) is/are most likely to undergo an electrophilic aromatic substitution reaction.(a)(b)(c)(d)(e)(f)(g)(h)(i) CH3 „NO2 O,N. CH3 O,N NO2
The following compound has four aromatic rings. Rank them in terms of increasing reactivity toward electrophilic aromatic substitution.
The following compound has two aromatic rings. Identify which ring is expected to be more reactive toward an electrophilic aromatic substitution reaction.
For each of the following compounds, determine whether the ring is activated or deactivated, then determine the strength of activation/deactivation, and finally, determine the expected directing effects.(a)(b)(c)(d)(e)(f) -NO2
Predict and explain the regiochemical outcome for chlorination of bromobenzene.
Does chlorination of chlorobenzene require the use of a Lewis acid? Explain why or why not?
When 1,3-dinitrobenzene is treated with nitric acid and sulfuric acid at elevated temperature, the product is 1,3,5-trinitrobenzene. Explain the regiochemical outcome of this reaction. In other words, explain why nitration takes place at the C5 position. Make sure to draw the sigma complex for each
When ethoxybenzene is treated with a mixture of nitric acid and sulfuric acid, two products are obtained each of which has the molecular formula C8H9NO3.(a) Draw the structure of each product.(b) Propose a mechanism of formation for the major product.
Draw the two major products obtained when toluene undergoes monobromination.
A Friedel-Crafts acylation is an electrophilic aromatic substitution in which the electrophile (E+) is an acylium ion. There are other methods of forming acylium ions, such as treatment of an anhydride with a Lewis acid. The resulting acylium ion can also be attacked by a benzene ring, resulting in
The following compound cannot be made with either a Friedel-Crafts alkylation or acylation. Explain.
Consider the following two compounds. How would you distinguish between them using:a) IR spectroscopy?b) 1H NMR spectroscopy?c) 13C NMR spectroscopy?
One of the constitutional isomers of xylene was treated with sodium, methanol, and ammonia to yield a product that exhibited five signals in its 13C NMR spectrum. Identify which constitutional isomer of xylene was used as the starting material.
Predict the product of the following reaction, and propose a mechanism for its formation. Na, CH,OH NH;
Identify which of the following compounds is expected to be a stronger base. Justify your choice. N. N.
Which of the following compounds would you expect to be most acidic? Justify your choice.
Consider the structures of the following alkyl chlorides:a. Which compound would you expect to undergo an SN1 process most readily? Justify your choice.b Which compound would you expect to undergo an SN1 process least readily? Justify your choice. .CI .CI CI
Identify each of the following compounds as aromatic, nonaromatic, or antiaromatic. Explain your choice in each case.a.b.c.d.e.f.g.h. :N-H
Firefly luciferin is the compound that enables fireflies to glow.a. The structure exhibits three rings. Identify which of the rings are aromatic.b. Identify which lone pairs are participating in resonance. Но ОН N. Firefly luciferin
Identify which of the following compounds are aromatic.a.b.c.d.e. O.
Students often confuse cyclohexane and benzene.In fact, these compounds have different properties, different geometry, and different reactivity. Each of these compounds also has a unique set of terminology. For each of the following terms, identify whether it is used in reference to benzene or to
A compound with molecular formula C8H8O produces an IR spectrum with signals at 3063, 1686, and 1646 cm-1. The 1H NMR spectrum of this compound exhibits a singlet at 2.6 ppm (I = 3H) and a multiplet at 7.5 (I = 5H). a) Draw the structure of this compound.b) What is the common name of this
Chloramphenicol is an antibiotic isolated from the Streptomyces venezuelae bacterium. Predict the expected isotope pattern in the mass spectrum of this compound (the relative heights of the molecular ion peak and surrounding peaks). Он он ОН CI .N. н O2N H-N Chloramphenicol
Identify the stronger nucleophile:(a) NaSH vs. H2S(b) Sodium hydroxide vs. water(c) Methoxide dissolved in methanol vs. methoxide dissolved in DMSO
For each of the following pairs of compounds, determine the relationship between the two compounds:a.b.
Draw the expected isotope pattern that would be observed in the mass spectrum of CH2BrCl. In other words, predict the relative heights of the peaks at M, M + 2, and M + 4.
Treating 1,2-cyclohexanediol with concentrated sulfuric acid yields a product with molecular formula C6H10O. An IR spectrum of the product exhibits a strong signal at 1720 cm-1. Identify the structure of the product, and show a mechanism for its formation.
Esters contain two C–O bonds and therefore will produce two separate stretching signals in the fingerprint region of an IR spectrum. One of these signals typically appears at approximately 1000 cm-1, while the other appears at approximately 1300 cm-1. Predict which of the two C–O bonds produces
Predict the expected isotope pattern in the mass spectrum of a compound with molecular formula C90H180Br2.
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![[H,SO,] Но НО R.](https://dsd5zvtm8ll6.cloudfront.net/si.question.images/images/question_images/1524/8/1/0/4105ae2c2aaab9221524810398303.jpg)
![[н]. H20 ОН Он он](https://dsd5zvtm8ll6.cloudfront.net/si.question.images/images/question_images/1524/8/0/9/8925ae2c0a490b4a1524809880332.jpg)
![ОН Na,Cr,0, H2SO4, H20 [H'] A EtOН soch 1) LIAI(OR)H `2) H20 xS NH3](https://dsd5zvtm8ll6.cloudfront.net/si.question.images/images/question_images/1524/8/0/9/5785ae2bf6a64bb51524809566185.jpg)
