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organic chemistry

Organic Chemistry 1st edition David R. Klein - Solutions

The triphenylmethyl radical reacts with itself to form the following dimer:Identify the type of radical process taking place, and draw the appropriate fishhook arrows. 2.
Draw a mechanism for the following intramolecular process:
For each of the following reactions identify the type of radical process involved, and draw the appropriate fishhook arrows:(a)(b)(c)(d)(e)(f) + HBr •Br:
The C-H bonds shown in red exhibit very similar BDEs, because homolytic cleavage of either bond results in a resonance-stabilized radical. Nevertheless, one of these C-H bonds is weaker than the other. Identify the weaker bond, and explain your choice: НЫ На
Identify the weakest C!H bond in each of the following compounds:(a)(b)(c)(d)
5-Methylcyclopentadiene undergoes homolytic bond cleavage of a C!H bond to form a radical that exhibits five resonance structures. Determine which hydrogen is abstracted and draw all five resonance structures of the resulting radical. 5-Methylcyclopentadiene
The triphenylmethyl radical was the first radical to be observed. Draw all resonance structures of this radical, and explain why this radical is unusually stable:
Draw resonance structures for each of the following radicals:(a)(b)(c)(d)
Rank the following radicals in order of stability:(a)(b)
Propose a plausible mechanism for the following transformation: н D3o+ .D
Identify the reagents necessary to achieve each transformation below. In each case, you will need to use at least one reaction from this chapter and at least one reaction from the previous chapter. The essence of each problem is to choose reagents that will achieve the desired stereochemical
Draw the structures of compounds A to D: NaNH, NaNH, 1) Excess NaNH, Br2 Br2 2) H20 (C3H12)
Draw the structure of each possible dichloride that can be used to prepare the following alkyne via elimination:
Propose a plausible synthesis for each of the following transformations:(a)(b)(c)(d)
Propose a plausible synthesis for each of the following transformations:(a)(b)(c)(d)
Compound A is an alkyne with molecular formula C5H8. When treated with aqueous sulfuric acid and mercuric sulfate, two different products with molecular formula C5H10O are obtained in equal amounts. Draw the structure of compound A, and draw the two products obtained.
An unknown alkyne is treated with ozone (followed by hydrolysis) to yield acetic acid and carbon dioxide. What is the structure of the alkyne?
1,2-Dichloropentane reacts with excess sodium amide in liquid ammonia to produce compound X. Compound X undergoes acid-catalyzed hydration to produce a ketone. Draw the structure of the ketone produced upon hydration of compound X.
Propose a plausible synthesis for each of the following transformations:(a)(b)(c)(d)(e)(f) Br Br
Compound A has molecular formula C7H12. Hydrogenation of compound A produces 2 methylhexane. Hydroboration-oxidation of compound A produces an aldehyde. Draw the structure of compound A, and draw the structure of the aldehyde produced upon hydroboration oxidation of compound A.
Compound A is an alkyne that reacts with two equivalents of H2 in the presence of Pd to give 2,4,6-trimethyloctane.(a) Draw the structure of compound A.(b) How many chirality centers are present in compound A?(c) Identify the locants for the methyl groups in compound A. Explain why the locants are
Draw the expected product of each of the following reactions, showing stereochemistry where appropriate: Н. D NANH, NH3
Propose a mechanism for each of the following transformations:(a)(b) Na NH3 (1) но ОН Н,о
Draw the structure of an alkyne that can be converted into 3-ethylpentane upon hydrogenation. Provide a systematic name for this compound.
When (R)-4-bromohept-2-yne is treated with H2 in the presence of Pt, the product is optically inactive. Yet, when (R)-4-bromohex-2-yne is treated with the same conditions, the product is optically active. Explain.
Predict the final product(s) for each sequence of reactions:(a)(b)(c)(d) Br Br. 1) Excess NaNH, 2) EECI 3) H2, Lindlar's catalyst 1) NANH, 2) Mel 3) 9-BBN 4) H202, NaOH H-CEC-H
Oleic acid and elaidic acid are isomeric alkenes:Oleic acid, a major component of butter fat, is a colorless liquid at room temperature. Elaidic acid, a major component of partially hydrogenated vegetable oils, is a white solid at room temperature. Oleic acid and elaidic acid can both be prepared
Draw the enol tautomer of each of the following ketones:(a)(b)(c)
Identify which of the following compounds represent a pair of keto-enol tautomers:(a)(b)(c)(d) -OH Он
Identify which of the following bases can be used to deprotonate a terminal alkyne:(a) NaOCH3(b) NaH(c) BuLi(d) NaOH(e) NaNH2
Identify the reagents you would use to achieve each of the following transformations: CI Br Br ОН CHз н
Predict the products obtained when 1-pentyne reacts with each of the following reagents:(a) H2SO4, H2O, HgSO4(b) 9-BBN followed by H2O2, NaOH(c) Two equivalents of HBr(d) One equivalent of HCl(e) Two equivalents of Br2 in CCl4(f) NaNH2 in NH3 followed by MeI(g) H2, Pt
Draw the products of each of the following acid-base reactions, and then predict the position of equilibrium in each case:(a)(b) н н NaH
Predict the products for each of the following reactions: H2 Lindlar's catalyst Н2 Pt
Predict the products for each of the following reactions:(a)(b) H2 Lindlar's catalyst :? H2 Pt -? Na NH, (1) ? На Ni,B На Pd Na NH3 (/)
Draw a bond-line structure for each of the following compounds:(a) 2-Heptyne(b) 2,2-Dimethyl-4-octyne(c) 3,3-Diethylcyclodecyne
Provide a systematic name for each of the following compounds:(a)(b)(c)(d) ci CI
Using ethylene (H2C=CH2) as your only source of carbon atoms, outline a synthesis for 3-hexanone.
Identify the reagents you would use to achieve each of the following transformations:(a) Conversion of all of the carbon atoms in bromoethane into CO2 gas(b) Conversion of all of the carbon atoms in 2-bromopropane into acetic acid (CH3COOH)
Propose a plausible synthesis for each of the following transformations:(a)(b)(c)(d)(e)(f) Н
Using acetylene as your only source of carbon atoms, outline a synthesis for 3-hexyne.
A terminal alkyne was treated with NaNH2 followed by propyl iodide. The resulting internal alkyne was treated with ozone followed by water, giving only one type of carboxylic acid. Provide a systematic, IUPAC name for the internal alkyne.
Preparation of 2,2-dimethyl-3-octyne cannot be achieved via alkylation of acetylene. Explain.
Starting with acetylene, show the reagents you would use to prepare the following compounds:(a) 1-Butyne(b) 2-Butyne(c) 3-Hexyne(d) 2-Hexyne(e) 1-Hexyne(f) 2-Heptyne(g) 3-Heptyne(h) 2-Octyne(i) 2-Pentyne(j)(k)
An alkyne with molecular formula C4H6 was treated with ozone followed by water to produce a carboxylic acid and carbon dioxide. Draw the expected product when the alkyne is treated with aqueous acid in the presence of mercuric sulfate.
An alkyne with molecular formula C6H10 was treated with ozone followed by water to produce only one type of carboxylic acid. Draw the structure of the starting alkyne and the product of ozonolysis.
Draw the major products that are expected when each of the following alkynes is treated with O3followed by H2O:(a)(b)(c)(d)
In the upcoming chapters, we will learn a twostep method for achieving the following transformation. In the meantime, use reactions we have already learned to achieve this transformation:
Identify the reagents you would use to carry out each of the following transformations:(a)(b) Br Br- CI. ČI
Identify the reagents you would use to carry out each of the following transformations:(a)(b) н
Identify the alkyne you would use to prepare each of the following compounds via hydroboration-oxidation:(a)(b)(c) エ
Draw the major product for each of the following reactions:(a)(b)(c) 1) 9-BBN 2) H2O2, NaOH 1) Disiamylborane 2) H20г, NaOH
Identify the alkyne you would use to prepare each of the following ketones via acid-catalyzed hydration:(a)(b)(c)
Draw the major product(s) expected when each of the following alkynes is treated with aqueous acid in the presence of mercuric sulfate (HgSO4):(a)(b)(c)(d)(e)
Consider the following equilibrium:These constitutional isomers rapidly interconvert in the presence of even trace amounts of acid and are therefore said to be tautomers of each other. Draw a mechanism for this transformation. Н,о* н z:
The following enols cannot be isolated. They rapidly tautomerize to produce ketones. In each case, draw the expected ketone, and show a mechanism for its formation under acid-catalyzed conditions (H3O+).(a)(b)(c)(d) он Но
An alkyne with molecular formula C5H8 is treated with excess HBr, and two different products are obtained, each of which has molecular formula C5H10Br2.(a) Identify the starting alkyne.(b) Identify the two products.
Suggest reagents that would achieve the following transformation: CI CI CI
Predict the major product expected for each of the following reactions:(a)(b)(c)(d)(e)(f) ? XS HCI CI 1) xs NANH/NH3 2) H,0 CI
An alkyne with molecular formula C5H8 was treated with sodium in liquid ammonia to give a disubstituted alkene with molecular formula C5H10. Draw the structure of the alkene.
Identify the reagents you would use to achieve each of the following transformations:(a)(b)
Identify the reagents you would use to achieve each of the following transformations:(a)(b)
Draw the major product expected when each of the following alkynes is treated with sodium in liquid ammonia:(a)(b)(c)(d)
Draw the major product expected from each of the following reactions:(a)(b) На ? Lindlar's catalyst На Pt -? На Ni,B -? На Ni
When 3,3-dichloropentane is treated with excess sodium amide in liquid ammonia, the initial product is 2-pentyne:However, under these conditions, this internal alkyne quickly isomerizes to form a terminal alkyne that is subsequently deprotonated to form an alkynide ion:The isomerization process is
For each of the following transformations, predict the major product, and draw a mechanism for its formation:(a)(b) 1) xs NANH,/NH3 Br 2) H,0 Br CI 1) xs NANH,/NH3 2) H,0
The pKa of CH3NH2 is 40, while the pKa of HCN is 9.(a) Explain this difference in acidity.(b) Can the cyanide anion (the conjugate base of HCN) be used as a base to deprotonate a terminal alkyne? Explain.
In each of the following cases, determine if the base is sufficiently strong to deprotonate the terminal alkyne. That is, determine whether the equilibrium favors formation of the alkynide ion.(a)(b)(c)(d)(e)(f) NANH2 H
Compound A is a terminal alkyne with molecular formula C6H10. Draw all four possible constitutional isomers that are possible structures for compound A, and provide a systematic name for each.
Although triple bonds have linear geometry, they do have some flexibility and can be incorporated in large rings. Cycloalkynes containing more than eight carbon atoms have been isolated and are stable at room temperature. When naming cycloalkynes that lack any other functional groups, the triple
Draw a bond-line structure for each of the following compounds:(a) 4,4-Dimethyl-2-pentyne(b) 5-Ethyl-2,5-dimethyl-3-heptyne
Provide a systematic name for each of the following compounds:(a)(b)(c)(d)
When 3-bromocyclopentene is treated with HBr, the observed product is a racemic mixture of trans-1,2-dibromocyclopentane. None of the corresponding cis-dibromide is observed. Propose a mechanism that accounts for the observed stereochemical outcome: Br Br Br Br HBr Br En Not observed
Propose a plausible mechanism for the following process, called iodolactonization: I2 ОН
Propose a plausible mechanism for each of the following reactions:a.b. Br Br2 ОН ф. [H,SO,] ОН
Suggest an efficient synthesis for the following transformation: CI Н нH
Propose a plausible mechanism for each of the following reactions:a.b. stitl. Он [H,SO,] и но Conc. H2SO4 но
Muscalure is the sex pheromone of the common housefly and has the molecular formula C23H46. When treated with O3followed by DMS, the following two compounds are produced. Draw two possible structures for muscalure. H. エ
Predict the major product(s) that are expected when each of the following alkenes is treated with Br2/H2O:a.b.c.d.
Predict the major product(s) for each of the following reactions:a.b.c.d. Br2 Br2
Compound X has molecular formula C5H10. In the presence of a metal catalyst, compound X reacts with one equivalent of molecular hydrogen to yield 2-methylbutane.a. Suggest three possible structures for compound X.b. Hydroboration-oxidation of compound X yields a product with no chirality centers.
In much the same way that they react with H2, alkenes also react with D2(deuterium is an isotope of hydrogen). Use this information to predict the product(s) of the following reaction: D2 Pt
Predict the product(s) for each of the following reactions:a.b.c.d.e.f. На Ni На Pd
Compound A has molecular formula C5H10. Hydroboration-oxidation of compound A produces an alcohol with no chirality centers. Draw two possible structures for compound A.
The products obtained from hydroboration-oxidation of cis-2-butene are identical to the products obtained from hydroboration-oxidation of trans-2-butene. Draw the products and explain why the configuration of the starting alkene is not relevant in this case.
Draw the product(s) obtained from hydroboration-oxidation of (E)-3-methyl-3-hexene.
Predict the product(s) for each of the following transformations:a.b.c.d.e.f. 1) ВН, THF 2) Н,О, NaOH 1) BH3 THF 2) H202, NaOH
Compound A has molecular formula C5H10. Hydroboration- oxidation of compound A produces 2-methylbutan-1-ol. Draw the structure of compound A: Compound A (C,H10) 1) BH, THF 2) H202, NaOH ОН
Below are several examples of hydroboration-oxidation. In each case, consider the expected regioselectivity, and then draw the product:a.b.c. 1) ВН, THF 2) H,O2, NaOH 1) BH3· THF 2) H2O2, NaOH
In the first step of the process (oxymercuration), nucleophiles other than water may be used. Predict the product when each of the following nucleophiles is used instead of water:a.b. 1) Hg(OAc)2, EtOH 2) NABH, 1) Hg(OAc)2, ETNH2 2) NaBH4
Predict the product for each reaction, and predict the products if an acid-catalyzed hydration had been performed rather than an oxymercuration- demercuration:a.b.c. 1) Hg(OAc)2, H20 2) NABH, 1) Hg(OAc)2, H20 2) NABH,
Using the reaction in the previous problem as a reference, propose a plausible mechanism for the following intramolecular reaction: [H,SO] он
If an alkene is protonated and the solvent is an alcohol rather than water, a reaction takes place that is very similar to acid-catalyzed hydration, but in the second step of the mechanism the alcohol functions as a nucleophile instead of water. Draw a plausible mechanism for the following process:
Draw a mechanism for each of the following transformations:a.b.c. он н,оt он Dilute H,SO,
Identify whether you would use dilute sulfuric acid or concentrated sulfuric acid to achieve each of the following transformations. In each case, explain your choice.a.b. Он [H,SO,] Н-о но. [H,SO,] + H20
In each of the following cases identify the alkene that is expected to be more reactive toward acid-catalyzed hydration.a.b. 2-Methyl-2-butene or 3-methyl-1-butene or
The following transformation proceeds through two successive carbocation rearrangements. Draw the mechanism, and explain why each of the carbocation rearrangements is favorable: Br Dilute HBr.
The mechanism of the following transformation involves a carbocation intermediate that rearranges in a way that we have not yet seen. Rather than occurring via a methyl shift or a hydride shift, a carbon atom of the ring migrates, thereby converting a secondary carbocation into a more stable,
Draw a mechanism for each of the following transformations:a.b.c. Br Dilute HЕг Dilute HBr Br, Br,
Predict the products for each of the following reactions. In some cases, the reaction produces a new chirality center, while in other cases, no new chirality center is formed. Consider that when drawing the product(s).a.b.c.d.e.f. HBr HCI,

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