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organic chemistry

Questions and Answers of Organic Chemistry

Propose a plausible mechanism for each of the following transformations.a.b.c.d.e.f. ОН 1) EtMgBr 2) Н-о 1) NaH OEt ОН 2) EtI но
Predict the products for each of the following.a.b.c.d.e.f.g.h. 1) RCO,H 2) MeMgBr 3) Н,о 1) Hg(OAc)2, MeOH 2) NaBH,
Problem 14.39 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare a racemic mixture of each of
When 5-bromo-2, 2-dimethyl-1-pentanol is treated with sodium hydride, a compound with molecular formula C7H14O is obtained. Identify the structure of this compound. NaH, Но Br С-Н40
Identify the reagents necessary to accomplish each of the following transformations. >
Methylmagnesium bromide reacts rapidly with ethylene oxide, it reacts slowly with oxetane, and it does not react at all with tetrahydrofuran.Explain this difference in reactivity. Oxetane Ethylene
The Williamson ether synthesis cannot be used to prepare tert-butyl phenyl ether.a. Explain why this method cannot be used in this case.b. Suggest an alternative method for preparing tert-butyl
When ethylene glycol is treated with sulfuric acid, 1, 4-dioxane is obtained. Propose a mechanism for this transformation: H,SO, Он Но Ethylene glycol 1,4-Dioxane
Tetrahydrofuran (THF) can be formed by treating 1, 4-butanediol with sulfuric acid. Propose a mechanism for this transformation. H,SO, H;SO. Он но 1,4-Butanediol Tetrahydrofuran (THF)
When 1, 4-dioxane is heated in the presence of HI, compound A is obtained:a. Draw the structure of compound A.b. If one mole of dioxane is used, how many moles of compound A are formed?c. Show a
Starting with cyclohexene and using any other reagents of your choice, show how you would prepare each of the following compounds.a.b.c. OH OMe
Draw all constitutionally isomeric ethers with molecular formula C4H10O. Provide a common name and a systematic name for each isomer.
Predict the products that are expected when each of the following compounds is heated with concentrated HBr.a.b.c.d.
Assign an IUPAC name for each of the following compounds.a.b.c.d.e.f.g. SH
Using compounds that possess no more than two carbon atoms, propose a plausible synthesis for the following compound.
Dimethoxyethane (DME) is a polar aprotic solvent often used for SN2 reactions. Propose a plausible synthesis for DME using acetylene and methyl iodide as your only sources of carbon atoms.
Propose a plausible synthesis for 1,4-dioxane using acetylene as your only source of carbon atoms. 1,4-Dioxane
Propose a plausible synthesis for each of the following transformations.a.b.c.d.e.f.g.h.i. Br ОН он ОН Br
Ethylene glycol is one of the main components of automobile antifreeze. Using iodoethane as your starting material, show how you could prepare ethylene glycol.
Propose a plausible synthesis for each of the following transformations.a.b.c.d.e. CN Но ОН Он En
Predict the products for each of the following reactions.a.b.c.d. SH 1) NaOH Br 2) Br SNa
What reagents would you use to prepare each of the following thiols:a.b.c. SH SH
Propose a mechanism for the following transformation. ОН Et Me [H,SO] н Etw Me -ОН
For each reaction, predict the product and draw the mechanism of its formation.a.b.
When meso-2, 3-epoxybutane is treated with aqueous sodium hydroxide, two products are obtained. Draw both products and describe their relationship.
When the following chiral epoxide is treated with aqueous sodium hydroxide, only one product is obtained, and that product is achiral. Draw the product and explain why only one product is formed.
For each of the following reactions, predict the product and draw the mechanism of its formation.a.b.c.d.e.f. 1) PhMgBr 2) H20 Me 1) NaCN 2) H20 *Me
Predict the products for each of the following reactions:a.b.c.d. но. Ti[OCH(CH,),1. (+)-DET о—о—н Он о-о-н THОCНICH) (-)-DET Он
Consider the following two compounds. When treated with NaOH, one of these compounds forms an epoxide quite rapidly, while the other forms an epoxide very slowly. Identify which compound reacts more
Identify the reactants you would use to form a racemic mixture of each of the following epoxides:a.b.c.d. Mery Н Н Me
Assign a name for each of the following compounds. Be sure to assign the configuration of each chirality center and indicate the configuration(s) at the beginning of the name.a.b.c. Me
Assign a name for each of the following compounds.a.b.c.
Assign a name for each of the following compounds.a.b.c.
Predict the products for each of the following reactions:a.b.c.d.e.f. excess HBr heat excess HI heat
Show how you would use an alkoxymercuration-demercuration to prepare isopropyl propyl ether using propene as your only source of carbon and any other reagents of your choosing.
How would you use an alkoxymercuration-demercuration to prepare dicyclopentyl ether using cyclopentene as your only source of carbon?
Show what reagents you would use to prepare each of the following ethers via an alkoxymercuration-demercuration.a.b.c.d. OEt
Can the following compound be prepared via a Williamson ether synthesis? Explain your answer.
The following cyclic ether can be prepared via an intramolecular Williamson ether synthesis. Show what reagents you would use to make this ether.
Show what reagents you would use to prepare each of the following ethers via a Williamson ether synthesis, and explain your reasoning.a.b.c. OMe
Identify the missing reagent needed to achieve the following transformations:a.b.c.d. Br KF benzene Br NaF benzene
There are six ethers with molecular formula C5H12O that are constitutional isomers.a) Draw all six constitutional isomers.b) Provide a systematic name for each of the six compounds.c) Provide a
Draw the structure of each of the following compounds.a. (R) -2-Ethoxy-1, 1-dimethylcyclobutaneb. Cyclopropyl isopropyl ether
Provide an IUPAC name for each of the following compounds.a.b.c.d.e. ČI
Determine whether the pinacol rearrangement, shown in the previous problem, is a reduction, an oxidation, or neither. Resonance stabilized Но ОН H,SO, Нeat
Determine whether the pinacol rearrangement, shown in the previous problem, is a reduction, an oxidation, or neither. Resonance stabilized ОН Но H,SO, Нeat
A carbocation is resonance stabilized when it is adjacent to an oxygen atom:Such a carbocation is even more stable than a tertiary carbocation. Using this information, propose a mechanism for the
Propose a mechanism for the following transformation: 1) Excess LAH 2) H20 CH3он
Show the reagents you would use to achieve the following transformation:
Propose a mechanism for the following transformation: но. 1) Excess MeMgBr 2) H20 ОН
Propose a mechanism for the following transformation: но. 1) Excess LAн, 2) H20 Он
Propose a structure for a compound with molecular formula C8H10O that exhibits the following1H NMR spectrum: Proton NMR Chemical shift (ppm)
Propose two possible structures for a compound with molecular formula C5H12O that exhibits the following13C NMR and IR spectra: Carton 13 NMR 29.1 9.5- 73.8- 100 90 80 70 60 50 20 10 Chemical shift
Propose a structure for a compound with molecular formula C3H8O that exhibits the following1H NMR and 13C NMR spectra: Proton NMR 0.5 5.0 4.5 4.0 3.5 3.0 2.0 1.5 1.0 25 Chemical shift (ppm) Carbon
Propose a structure for a compound with molecular formula C10H14O that exhibits the following1H NMR spectrum. Proton NMR Chemical shift (ppm)
Propose a plausible synthesis for each of the following transformations:a.b.c.d.e.f.g.h.i.j.k.l.m.n.o.p.q.r.s. H. н エ
Identify the reagents that would be necessary to accomplish each of the transformations shown here: н ОН Br
Propose a plausible mechanism for each of the following transformations.a.b. Он 1) MeMgBr 2) H20 1) Excess MeMgBr 2) H20 Но Он
Predict the products for each of the following:a.b.c.d.e.f. 1) O3 2) DMS 3) Excess LAH 4) H20 1) O3 2) DMS 3) Excess LAH 4) H20
Identify the reagents you would use to accomplish each of the following transformation.a.b.c.d.e.f. Он ОН H.
Draw the mechanism for each of the following reaction.a.b.c. OH py
Draw the mechanism for each of the following reaction.a.b.c. Он socl, Py Br ОН PBr3
Predict the product and draw the mechanism for each of the following reactions:a.b.c. ? 1) LAH 2) H20
Predict the product and draw the mechanism for each of the following reactions:a.b.c. 1) LAH 2) H20 1) LAH 2) H20
Using 2-propanol as your only source of carbon, show how you would prepare 2-methyl-2-pentanol.
Consider the following sequence of reactions, and identify the reagents a€“h. ОН H. об -о ob-o об -об ОН он ОН Br Н
Consider the following sequence of reactions, and identify the structures of compounds A, B, and C. Mg Compound A (CeH11Br) Compound B 1) 2) H20 H,SO4 Compound C Heat
Acid-catalyzed hydration of 1-methylcyclohexene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explane.
Acid-catalyzed hydration of 1-methylcyclohexene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explane.
Propose a mechanism for the following reaction. NaH Br ОН
What reagents would you use to perform each of the following transformations?a.b. H. н ОН
Each of the following alcohols can be prepared via reduction of a ketone or aldehyde. In each case, identify the aldehyde or ketone that would be required.a.b.c.d. HO. HO.
Each of the following alcohols can be prepared via reduction of a ketone or aldehyde. In each case, identify the aldehyde or ketone that would be required.a.b.c.d. Но. Он ОН
Each of the following alcohols can be prepared via reduction of a ketone or aldehyde. In each case, identify the aldehyde or ketone that would be required.a.b.c.d. Но. Он ОН
Starting with 1-butanol, show the reagents you would use to prepare each of the following compounds.a.b.c.d.e. H. Но.
Acid-catalyzed hydration of 3, 3-dimethyl-1-butene produces 2,3-dimethyl-2-butanol. Show a mechanism for this reaction.
Predict the major product of the reaction between 1-butanol and:(a) PBr3 (b) SOCl2, py(c) HCl, ZnCl2 (d) H2SO4, heat(e) PCC, CH2Cl2 (f ) Na2Cr2O7, H2SO4, H2O(g) Li (h) NaH(i)
Draw resonance structures for each of the following anions.a.b.c.
Rank each set of alcohols below in order of increasing acidity.a.b.c. CI CI .CI CI CI CI ОН Он Он ОН ОН ОН
Draw and name all constitutionally isomeric alcohols with molecular formula C4H10O.
Draw the structure of each compound:(a) cis-1, 2-Cyclohexanediol (b) Isobutanol(c) 2, 4, 6-Trinitrophenol (d) (R)-2, 2-Dimethyl-3-heptanol(e) Ethylene glycol (f) (S)-2-Methyl-1-butanol
Assign an IUPAC name for each of the following compounds:a.b.c.d. но.
When isopropylbenzene (cumene) is treated with NBS and irradiated with UV light, only one product is obtained. Propose a mechanism, and explain why only one product is formed. Br NBS hv
Draw all resonance structures of the radical produced when a hydrogen atom is abstracted from the OH group in BHT: ОН Butylated hydroxyfoluene (BHT)
Rank each group of radicals in order of increasing stability:(a)(b)
Consider all of the different C!H bonds in cyclopentene, and rank them in order of increasing bond strength: H.
Draw all resonance structures for each of the following radicals:(a)(b)(c)(d)(e)
The initiation step for radical addition of HBr is highly endothermic:(a) Explain how this step can be thermodynamically favorable at high temperature even though it is endothermic.(b) Explain why
Predict the products for each reaction. In each case, be sure to consider whether a chirality center is being generated and then draw all expected stereoisomers.(a)(b)(c)(d)(e)(f) HЕг ROOR HBr ROOR
Compare the structure of vitamin E with the structures of BHT and BHA, and then determine which hydrogen atom is most easily abstracted from vitamin E.
Most supersonic planes produce exhaust of hot gases containing many compounds, including nitric oxide (NO). Nitric oxide is a radical that is believed to play a role in ozone depletion. Propose
When 2-methyl-2-butene is treated with NBS and irradiated with UV light, five different monobromination products are obtained, one of which is a racemic mixture of enantiomers. Draw all five
Predict the products when each of the following compounds is treated with NBS and irradiated with UV light:(a)(b)(c)(d)
Compound A has molecular formula C5H11Br. When compound A is treated with bromine in the presence of UV light, the major product is 2,2-dibromopentane. Treatmentof compound A with NaSH (a strong
Predict the stereochemical outcome of radical bromination of the following alkanes:(a)(b)(c)(d)
Compound A has molecular formula C5H12 and undergoes monochlorination to produce four different constitutional isomers.(a) Draw the structure of compound A.(b) Draw all four monochlorination
Predict the major product obtained upon radical bromination of each of the following compounds:(a)(b)(c)
In practice, the chlorination of methane often produces many by-products. For example, ethyl chloride is obtained in small quantities. Can you suggest a mechanism for the formation of ethyl chloride?
Draw a mechanism for each of the following processes:(a) Chlorination of methylene chloride to produce chloroform(b) Chlorination of chloroform to produce carbon tetrachloride(c) Chlorination of
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.

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