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organic chemistry

Questions and Answers of Organic Chemistry

Give the expected product(s) of the reaction of trans-3-methylcyclopentanol with each of the reagents in Problem 38.(a) K+-OC(CH3)3(b) Sodium metal(c) CH3Li(d) Concentrated HI(e) Concentrated HCl(f)
Give the expected product(s) of the reaction of 1-pentanol with each of the following reagents.(a) K+-OC(CH3)3(b) Sodium metal(c) CH3Li(d) Concentrated HI(e) Concentrated HCl(f) FSO3H(g) Concentrated
Give the expected main product of the reaction of each of the alcohols in Problem 31 with PBr3. Compare the results with those of Problem 33.
What are the most likely product(s) of each of the following reactions? CH3 CH3 Conc. HI CH,CH,OH, H,SO, (а) HO (b) CH;CCH,OH CH3 CH,OH CH3 I Conc. H.SO, 180°с (с) (d) CH,С— СНCH, ČH3
Give detailed mechanisms and final products for the reaction of 3-methyl-2-pentanol with each of the reagents that follow.(a) NaH(b) Concentrated HBr(c) PBr3(d) SOCl2(e) Concentrated H2SO4 at
Write all sensible products of the reaction of each of the alcohols in Problem 31 with concentrated aqueous HBr.In Problem 31 OH (а) CH-CH-CH,Oн (b) CH;CHCH3 (c) CH;CH,CH,CH,OH OH (d)
Write all products of the reaction of each of the alcohols in Problem 31 with concentrated H2SO4 under elimination conditions.In Problem 31 OH (а) CH-CH-CH,Oн (b) CH;CHCH3 (c) CH;CH,CH,CH,OH OH (d)
Name the following alcohols according to the IUPAC nomenclature system. Indicate stereochemistry (if any) and label the hydroxy groups as primary, secondary, or tertiary. OH Br OH (a) CH;CH,CHCH; (b)
Which of the following isomeric carbocations is the most stable? CH,+ CH3 (а) (b) -CH3 CH3 (с) (d)
In this transformation,what is the best structure for A?(a) BrCH2CH2CH(CH3)2(b)(c)(d) Н-О, асetone A CH;CH,C(CH3)2 ÓH
Consider the general substitution-elimination reactions of the bromoalkanes.How do the reaction mechanisms and product formation differ when the structure of the substrate and reaction conditions
Give the major product(s) of the following reactions. Indicate which of the following mechanism(s) is in operation: SN1, SN2, E1, or E2. If no reaction takes place, write “no reaction.”
How would each reaction in Problem 25 be affected by the addition of each of the following substances to the solvolysis mixture?(a) H2O(b) KI(c) NaN3(d) CH3CH2OCH2CH3In Problem 25 CH3 Br CI CH,CH;
Classify each of the following common objects as being either chiral or achiral. Assume in each case that the object is in its simplest form, without decoration or printed labels.(a) A ladder;(b) A
Typical hydrocarbon fuels (e.g., 2,2,4-trimethylpentane, a common component of gasoline) have very similar heats of combustion when calculated in kilocalories per gram.(a) Calculate heats of
Propanalare isomers with the formula C3H6O. The heat of combustion of propanal is - 434.1 kcal mol-1, that of acetone -427.9 kcal mol-1.(a) Write a balanced equation for the combustion of either
Write balanced equations for the combustion of each of the following substances (molecular formulas may be obtained from Table 3-7):(a) methane;(b) propane;(c) cyclohexane;(d) ethanol;(e) sucrose.
Cationic polymerization of para-methoxystyrene occurs much more rapidly than cationic polymerization of styrene. Explain this difference in rate.
When a solution of aqueous sodium hydroxide is spilled on polyester clothing, a hole develops in the fabric. Describe how the polyester is destroyed.
Using vinyl acetate as your only source of carbon atoms, design a synthesis for the following polymer: OAc Vinyl acetate
As described in the Practically Speaking box in Section 27.7, poly(vinyl alcohol) is used as a precursor to make PVB for use in automobile windshields. Poly(vinyl alcohol) can be prepared by
Draw the polymer that is expected when the following monomers react under acidic conditions. NH2 [н] -Н,о H,N
Consider the structure of the following polymer.(a) Draw the monomers you would use to prepare this polymer.(b) Determine whether this polymer is a step-growth polymer or a chain-growth polymer.(c)
Draw segments of the following polymers, indicating the stereochemistry with wedges and/or dashes.(a) Syndiotactic poly(vinyl chloride)(b) Isotactic polystyrene
Cationic polymerization of para-methoxystyrene occurs much more rapidly than cationic polymerization of metamethoxystyrene. Explain this difference in rate.
Anionic polymerization of para-nitrostyrene occurs much more rapidly than anionic polymerization of styrene. Explain this difference in rate.
Nylon 6 is a polyamide used in the manufacture of ropes. It can be prepared via hydrolysis of Îµ caprolactam to form Îµ-aminocaproic acid followed by acid-catalyzed
Olestra is a noncaloric oil substitute that is produced by esterifying sucrose with eight equivalents of fatty acids obtained from the hydrolysis of vegetable oils. The eight fatty acid residues give
When 3-methyl-1-butene is treated with a catalytic amount of BF3 and H2O, a cationic polymerization process occurs, but the expected homopolymer is not formed. Instead, a random copolymer is
When ethylene oxide is treated with a strong nucleophile, the epoxide ring is opened to form an alkoxide ion that can function as a nucleophile to attack another molecule of ethylene oxide. This
Would these pairs of monomers form chain-growth or step-growth polymers?(a)(b) -NH2 H,N- CI CI CI CN
Should this polymer be classified as a chain-growth polymer or a step-growth polymer?
Polyisobutylene cannot be described as isotactic, syndiotactic, or atactic. Explain.
Polyethylene is used to make Ziploc bags and folding tables. Identify which of these applications is most likely to be made from HDPE and which is most likely to be made from LDPE.
The following monomer can be polymerized under either acidic or basic conditions. Explain. CN OMe
Propose a mechanism for the acid-catalyzed hydrolysis of PET to regenerate the monomers terephthalic acid and ethylene glycol.
Draw and name the polymer that results when each of the following monomers undergoes polymerization.(a)(b)(c) NO2 Н C: Н Н Nitroethylene Н CN C= н Н Acrylonitrile
Polyformaldehyde, sold under the trade name Delrin, is a strong polymer used in the manufacture of many guitar picks. It is prepared via the acid-catalyzed polymerization of formaldehyde.(a) Draw the
Kodel is a synthetic polyester with the following structure.(a) Identify what monomers you would use to make Kodel.(b) Would you use acidic conditions or basic conditions for this polymerization
Explain why vinyl shower curtains develop cracks over time.
Draw the structures of the monomers required to make the following alternating copolymer. E-0-E I-O- H-CIH
Draw a region of a block copolymer constructed from isobutylene and styrene.
Draw a region of an alternating copolymer constructed from vinyl chloride and ethylene.
Identify which of the following monomers would be most reactive toward cationic polymerization. OAc CN CI
Identify which of the following monomers would be most reactive toward anionic polymerization: CH3 OAc CN
Nitroethylene undergoes anionic polymerization so rapidly that it is difficult to isolate nitroethylene without it polymerizing. Explain.
Identify the repeating unit of the polymer formed from each of the following reactions, and then determine whether the polymer is a chain-growth or a step-growth polymer.(a)(b)(c) NH2 Со-н [н]
Quiana is a synthetic polymer that can be used to make fabric that mimics the texture of silk. It can be prepared from the following monomers:(a) Draw the structure of Quiana.(b) Is Quiana a
Draw the monomer(s) required to make each of the following condensation polymers:(a)(b) エーZ ZーエエーZ
Determine whether the following pairs of monomers would form chain-growth polymers or step growth polymers.(a)(b) Но- -он Но ОН NO2 Ph
Draw the condensation polymer produced when 1,4-cyclohexanediol is treated with phosgene.
Identify the condensation polymer that would be produced when phosgene is treated with 1,4 butanediol.
Identify the monomers required to make each of the following condensation polymers.(a)(b)
Kevlar is a condensation polymer used in the manufacture of bulletproof vests. Identify the monomers required for the preparation of Kevlar. Н Н Н Н Kevlar
Draw the polymer that would be generated from the acid-catalyzed reaction between oxalic acid and resorcinol. HO [H*) НО Он Но Oxalic acid Resorcinol
Draw the mechanism of formation of PET in acidic conditions. It might be helpful to first review the mechanism for the Fischer esterification process.
A tube of superglue will harden if it remains open too long in a humid environment. Draw a mechanism that shows how superglue polymerizes in the presence of atmospheric moisture. When drawing your
Many monomers that readily undergo cationic polymerization, such as isobutylene, will not readily undergo anionic polymerization. Styrene, however, can be effectively polymerized via cationic,
Arrange the following monomers in order of reactivity toward anionic polymerization. CI NO2
Arrange the following monomers in order of reactivity toward cationic polymerization. NO2 CH3 OAc
Determine whether preparation of each of the following polymers would best be achieved via cationic addition or anionic addition.(a)(b)(c)(d)(e)(f) CN CN CN CN CN CN OMe OMe OMe OMe
Identify the monomers required to make the following alternating copolymer: CHз H -ċ-C-Ċ- CH3 H &--т
Draw a region of a block copolymer constructed from propylene and vinyl chloride.
Draw a region of an alternating copolymer constructed from styrene and ethylene.
Sodium polyacrylate is a synthetic polymer used in diapers, because of its ability to absorb several hundred times its own mass of water. This extraordinary polymer is made from another polymer,
Draw and name the polymer that results when each of the following monomers undergoes polymerization.(a)(b)(c) OAc c=C Vinyl acetate Н Br C=C Н Н Vinyl bromide
The following compound was isolated from nerve cells.(a) Describe how this compound differs in structure from fats and oils.(b) Three products are obtained when this compound is hydrolyzed with
Starting with the following compound and using any other reagents of your choice, outline a synthesis for trimyristin. H.
Limonene is an optically active compound isolated from the peels of lemons and oranges.(a) Is limonene a monoterpene or a diterpene?(b) Treatment of limonene with excess HBr yields a compound with
Identify the reagents you would use to convert oleic acid into each of the following compounds.(a) Stearic acid(b) Ethyl stearate(c) 1-Octadecanol(d) Nonanedioic acid(e) 2-Bromostearic acid
Identify the products expected when estradiol is treated with each of the following reagents.(a) Excess Br2(b) PCC(c) A strong base followed by excess ethyl iodide(d) Excess acetyl chloride in the
Treatment of cholesterol with MCPBA could potentially produce two diastereomeric epoxides.(a) Draw both diastereomeric epoxides.(b) Only one of these epoxides is formed. Predict which one, and
Sphingomyelins are lipids with the following general structure:(a) Identify the polar head and all hydrophobic tails in sphingomyelins.(b) Do sphingomyelins have the appropriate structural features
Draw the enantiomer of cholesterol.
Draw the structure of an optically active triglyceride that contains two oleic acid residues and one palmitic acid residue.
Draw the structure of an optically inactive triglyceride that contains two oleic acid residues and one palmitic acid residue.
Draw a mechanism for the base-catalyzed transesterification of trimyristin using ethanol in the presence of sodium hydroxide.
Draw a mechanism for the transesterification of trimyristin using excess isopropanol in the presence of an acid catalyst.
Draw the structures of trimyristin and tripalmitin and determine which is expected to have the lower melting point. Explain your choice.
One of the compounds present in carnauba wax was isolated, purified, and then treated with aqueous sodium hydroxide to yield an alcohol with 30 carbon atoms and a carboxylate ion with 20 carbon
Identify which of the following statements applies to tristearin.(a) It is a solid at room temperature.(b) It is unreactive toward molecular hydrogen in the presence of Ni.(c) It undergoes hydrolysis
Which of the following statements applies to triolein?(a) It is a solid at room temperature.(b) It is unreactive toward molecular hydrogen in the presence of Ni.(c) It undergoes hydrolysis to produce
Which of the fatty acids in the previous problem has four carbon-carbon double bonds?
Identify each of the following fatty acids as saturated or unsaturated.(a) Palmitic acid (b) Myristic acid (c) Oleic acid(d) Lauric acid (e) Linoleic acid (f) Arachidonic acid
Identify whether hexane or water would be more appropriate for extracting terpenes from plant tissues. Explain your choice.
Arrange the following compounds in order of increasing water solubility.(a) A triglyceride constructed from one equivalent of glycerol and three equivalents of myristic acid(b) A diglyceride
Tristearin is less susceptible to becoming rancid than triolein. Explain.
Draw the structure of trans-oleic acid.
Which of the following compounds are lipids?(a) l-Threonine (b) 1-Octanol(c) Lycopene (d) Trimyristin(e) Palmitic acid (f) d-Glucose(g) Testosterone (h) d-Mannose
The fatty acid residues in this triglyceride are saturated, and will not react with molecular hydrogen.
Draw two different cephalins that contain one lauric acid residue and one myristic acid residue. Are both of these compounds chiral?
Predict the product(s) formed when tripalmitolein is treated with each of the following reagents.(a) Excess H2, Ni(b) Excess NaOH, H2O
Identify each of the following compounds as a wax, triglyceride, phospholipid, steroid, prostaglandin, or terpene.(a) Stanozolol (b) Lycopene(c) Tristearin (d) Distearoyl lecithin(e)
Draw a mechanism for the biosynthesis of Î±-farnesene starting with dimethylallyl pyrophosphate and isopentenyl pyrophosphate. a-Farnesene
Draw a mechanism for the following transformation. OPP OPP OPP
Determine whether each of the following compounds is a terpene.(a)(b)(c)(d) ОН ОН
Circle the isoprene units in each of the following compounds.(a)(b)(c) ОН Menthol HO Grandisol
Classify each prostaglandin according to the instructions provided in Section 26.7.In section 26.7€¢ Prostaglandins are biochemical regulators that are even more powerful than
Prednisolone acetate is an anti-inflammatory agent in clinical use. It is similar in structure to cortisol, with the following two differences: (1) Prednisolone acetate exhibits a double bond between
Draw the hypothetical ring-flip of trans-decalin, and explain why it does not occur. Use this analysis to explain why cholesterol has a fairly rigid three-dimensional geometry.

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