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1 Million+ Step-by-step solutions Q:A compound is a cyclic ether of molecularA compound is a cyclic ether of molecular formula C9H10O. Its 13C NMR spectrum is shown in Figure 16.11. Oxidation of the compound with sodium dichromate and sulfuric acid gave 1, 2- benzenedicarboxylic acid. What is the compound?Q:Which of the isomeric C4H10O alcoholsWhich of the isomeric C4H10O alcohols can be prepared by hydrogenation of aldehydes? Which can be prepared by hydrogenation of ketones? Which cannot be prepared by hydrogenation of a carbonyl compound?Q:Sodium borodeuteride (NaBD4)Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagents for introducing deuterium, the mass 2 isotope of hydrogen, into organic compounds. Write the structure of the organic product of the following reactions, clearly showing the position of all the deuterium atoms in each:Q:Give the structure of an esterGive the structure of an ester that will yield a mixture containing equimolar amounts of 1-propanol and 2-propanol on reduction with lithium aluminum hydrideQ:Each of the following alcohols has been preparedEach of the following alcohols has been prepared by reaction of a Grignard reagent with ethylene oxide. Select the appropriate Grignardreagent in each case.Q:Write equations showing how 3-methyl-1,5-pentanediolWrite equations showing how 3-methyl-1,5-pentanediol could be prepared from a dicarboxylic acid or a diester.Q:Give the structures, including stereochemistry, for the diols obtained by hydroxylationGive the structures, including stereochemistry, for the diols obtained by hydroxylation of cis-2-butene and trans-2-butene.Q:On the basis of the mechanismOn the basis of the mechanism for the acid-catalyzed formation of diethyl ether from ethanol in Figure 15.2, write a stepwise mechanism for the formation of oxane from 1,5-pentanediol (see the equation in the preceding paragraph).Q:Write the structure of the ester formedWrite the structure of the ester formed in each of the following reactions:Q:A similar conclusion may be drawnA similar conclusion may be drawn by considering the reactions of the cis and Tran isomers of 4-tert-butylcyclohexanol with acetic anhydride. On the basis of the information just presented, predict the product formed from each stereoisomer.Q:Alfred Nobel’s fortune was based on his 1866Alfred Nobel’s fortune was based on his 1866 discovery that nitroglycerin, which is far too shock-sensitive to be transported or used safely, can be stabilized by adsorption onto a substance called kieselguhr to give what is familiar to us as dynamite. Nitroglycerin is the trinitrate of glycerol (1, 2, 3 – propanetriol). Write a structural formula or construct a molecular model of nitroglycerin.Q:Predict the principal organic product of each of the following 5898Predict the principal organic product of each of the following reactions: Discuss.Q:The mechanism of enzymatic oxidationThe mechanism of enzymatic oxidation has been studied by isotopic labeling with the aid of deuterated derivatives of ethanol. Specify the number of deuterium atoms that you would expect to find attached to the dihydropyridine ring of the reduced form of the nicotinamide adenine dinucleotide coenzyme following enzymatic oxidation of each of the alcohols given:
(c) CH3CH2ODQ:Predict the products formed on oxidationPredict the products formed on oxidation of each of the following with periodic acid:
(a) HOCH2CH2OHQ:Outline a synthesisOutline a synthesis of 1-hexanethiol from 1-hexanol.Q:The main components of a skunk’sThe main components of a skunk’s scent fluid are 3-methyl-1-butanethiol and cis- and trans-2-butene-1-thiol. Write structural formulas for each of these compounds.Q:Three of the most intense peaks in the massThree of the most intense peaks in the mass spectrum of 2-methyl-2-butanol appear at m/z 59, 70, and 73. Explain the origin of these peaks.Q:Write chemical equationsWrite chemical equations, showing all necessary reagents, for the preparation of 1-butanol by each of the following methods:
(a) Hydroboration–oxidation of an alkene
(b) Use of a Grignard reagent
(c) Use of a Grignard reagent in a way different from part (b)
(d) Reduction of a carboxylic acid
(e) Reduction of a methyl ester
(f) Reduction of a butyl ester
(g) Hydrogenation of an aldehyde
(h) Reduction with sodium borohydrideQ:Write chemical equations, showingWrite chemical equations, showing all necessary reagents, for the preparation of 2-butanol by each of the following methods:
(a) Hydroboration–oxidation of an alkene
(b) Use of a Grignard reagent
(c) Use of a Grignard reagent different from that used in part (b)
(d–f) Three different methods for reducing a ketoneQ:Write chemical equations, showing all necessaryWrite chemical equations, showing all necessary reagents, for the preparation of tert-butyl alcohol by:
(a) Reaction of a Grignard reagent with a ketone
(b) Reaction of a Grignard reagent with an ester of the type RCOCH3Q:Which of the isomeric C5H12O alcoholsWhich of the isomeric C5H12O alcohols can be prepared by lithium aluminum hydride reduction of?
(a) An aldehyde
(c) A carboxylic acid
(b) A ketone
(d) An ester of the type RCOCH3Q:Evaluate the feasibility of the routeEvaluate the feasibility of the routeQ:Sorbitol is a sweetener often substitutedSorbitol is a sweetener often substituted for cane sugar, since it is better tolerated by diabetics. It is also an intermediate in the commercial synthesis of vitamin C. Sorbitol is prepared by high-pressure hydrogenation of glucose over a nickel catalyst. What is the structure (including stereochemistry) of sorbitol?Q:Write equations showing how 1-phenylethanol could be preparedWrite equations showing how 1-phenylethanol (C6H5CHCH3) could be prepared from each of the following starting materials:
(c) Benzyl alcohol
Q:Write equations showing how 2-phenylethanolWrite equations showing how 2-phenylethanol (C6H5CH2CH2OH) could be prepared from each of the following starting materials:
(c) 2-Phenylethanal (C6H5CH2CHO)
(d) Ethyl 2-phenylethanoate (C6H5CH2CO2CH2CH3)
(e) 2-Phenylethanoic acid (C6H5CH2CO2H)Q:Outline practical syntheses of eachOutline practical syntheses of each of the following compounds from alcohols containing no more than four carbon atoms and any necessary organic or inorganic reagents. In many cases the desired compound can be made from one prepared in an earlier part of the problem.
(c) 2-HexanolQ:Outline practical synthesesOutline practical syntheses of each of the following compounds from benzene, alcohols, and any necessary organic or inorganic reagents:
(a) 1-Chloro-2-phenylethaneQ:Show how each of the following compounds can be synthesizedShow how each of the following compounds can be synthesized from cyclopentanol and any necessary organic or inorganic reagents. In many cases the desired compound can be made from one prepared in an earlier part of the problem.
(c) trans-2-PhenylcyclopentanolQ:Write the structure of the principal organic product formed in the reactionWrite the structure of the principal organic product formed in the reaction of 1-propanol with each of the following reagents:
(a) Sulfuric acid (catalytic amount), heat at 140°C
(b) Sulfuric acid (catalytic amount), heat at 200°C
(c) Nitric acid (H2SO4 catalyst)
(d) Pyridinium chlorochromate (PCC) in dichloromethane
(e) Potassium dichromate (K2Cr2O7) in aqueous sulfuric acid, heat
(f) Sodium amide (NaNH2)Q:Each of the following reactions has been reported in the 5916Each of the following reactions has been reported in the chemical literature. Predict the product in each case, showing stereochemistry where appropriate.Q:On heating 1, 2, 4-butanetriol in the presenceOn heating 1, 2, 4-butanetriol in the presence of an acid catalyst, cyclic ether of molecular formula C4H8O2 was obtained in 81–88% yield. Suggest a reasonable structure for this product.Q:Give the Cahn–Ingold–Prelog R and SGive the Cahn–Ingold–Prelog R and S descriptors for the diol(s) formed from cis-2-pentene and trans-2-pentene on treatment with the osmium tetraoxide/tert-butyl hydroperoxide reagent.Q:Suggest reaction sequences and reagentsSuggest reaction sequences and reagents suitable for carrying out each of the following conversions. Two synthetic operations are required in each case.Q:The fungus responsible for Dutch elm diseaseThe fungus responsible for Dutch elm disease is spread by European bark beetles when they burrow into the tree. Other beetles congregate at the site, attracted by the scent of a mixture of chemicals, some emitted by other beetles and some coming from the tree. One of the compounds given off by female bark beetles is 4-methyl-3-heptanol. Suggest an efficient synthesis of this pheromone from alcohols of five carbon atoms or fewer.Q:Show by a series of equations how you could prepare 3-methylpentaneShow by a series of equations how you could prepare 3-methylpentane from ethanol and any necessary inorganic reagents.Q:(a) The cis isomer of 3-hexen-1-ol (CH3CH2CH(a) The cis isomer of 3-hexen-1-ol (CH3CH2CH═CHCH2CH2OH) has the characteristic odor of green leaves and grass. Suggest a synthesis for this compound from acetylene and any necessary organic or inorganic reagents.
(b) One of the compounds responsible for the characteristic odor of ripe tomatoes is the cis isomer of CH3CH2CH═CHCH2CH═O. How could you prepare this compound?Q:R. B. Woodward was one of the leading organicR. B. Woodward was one of the leading organic chemists of the middle part of the twentieth century. Known primarily for his achievements in the synthesis of complex natural products, he was awarded the Nobel Prize in chemistry in 1965. He entered Massachusetts Institute of Technology as a 16-year-old freshman in 1933 and four years later was awarded the Ph.D. While a student there he carried out a synthesis of estrone, a female sex hormone. The early stages of Woodward’s estrone synthesis required the conversion of m-methoxybenzaldehyde to m-methoxybenzyl cyanide, which was accomplished in three stepsQ:Complete the following series of equationsComplete the following series of equations by writing structural formulas for compounds A through I:Q:When 2-phenyl-2-butanol is allowedWhen 2-phenyl-2-butanol is allowed to stand in ethanol containing a few drops of sulfuric acid, the following ether is formed:Q:Suggest a chemical test that would permitSuggest a chemical test that would permit you to distinguish between the two glycerol monobenzyl ethers shown.Q:Choose the correct enantiomer of 2-butanolChoose the correct enantiomer of 2-butanol that would permit you to prepare (R)-2-butanethiol by way of a p-toluenesulfonate esterQ:The amino acid cysteine has the structureThe amino acid cysteine has the structure shown:Q:A diol (C8H18O2) does not react with periodicA diol (C8H18O2) does not react with periodic acid. Its 1H NMR spectrum contains three singlets at δ 1.2 (12 protons), 1.6 (4 protons), and 2.0 ppm (2 protons). What is the structure of this diol?Q:Identify compound A (C8H10O) on the basisIdentify compound A (C8H10O) on the basis of its 1H NMR spectrum (Figure 15.6). The broad peak at δ 2.1 ppm disappears when D2O is added.Q:Identify each of the following (C4H10O)Identify each of the following (C4H10O) isomers on the basis of their 13C NMR spectra:
(a) δ 31.2 ppm: CH3
(c) δ 18.9 ppm: CH3, area 2
δ 68.9 ppm: C
δ 30.8 ppm: CH, area 1
(b) δ 10.0 ppm: CH3
δ 69.4 ppm: CH2, area 1
δ 22.7 ppm: CH3
δ 32.0 ppm: CH2
δ 69.2 ppm: CHQ:A compound C3H7ClO2 exhibited three peaksA compound C3H7ClO2 exhibited three peaks in its 13C NMR spectrum at δ 46.8 (CH2), δ 63.5 (CH2), and δ 72.0 ppm (CH). What is the structure of this compound?Q:A compound C6H14O has the 13C NMR spectrumA compound C6H14O has the 13C NMR spectrum shown in Figure 15.7. Its mass spectrum has a prominent peak at m/z 31. Suggest a reasonable structure for this compound.Q:What fatty acids are producedWhat fatty acids are produced on hydrolysis of 2-oleyl-1, 3- distearylglycerol? What other triacylglycerol gives the same fatty acids and in the same proportions as 2-oleyl-1, 3-distearylglycerol?Q:Using HSCoA and HS─ACP as abbreviationsUsing HSCoA and HS─ACP as abbreviations for coenzyme A and acyl carrier protein, respectively, write a structural formula for the tetrahedral intermediate in the preceding reaction.Q:By analogy to the intermediates givenBy analogy to the intermediates given in steps 1–4 of Figure 26.3, write the sequence of acyl groups that are attached to the acyl carrier protein in the conversion ofQ:What is the absolute configuration (R or S) of L-glycerolWhat is the absolute configuration (R or S) of L-glycerol 3- phosphate? What must be the absolute configuration of the naturally occurring phosphatidic acids biosynthesized from it?Q:Spermaceti is a wax obtained from the sperm whale.Spermaceti is a wax obtained from the sperm whale. It contains, among other materials, an ester known as cetyl palmitate, which is used as an emollient in a number of soaps and cosmetics. The systematic name for cetyl palmitate is hexadecyl hexadecanoate. Write a structural formula for this substance.Q:Arachidonic acid is the biosynthetic precursorArachidonic acid is the biosynthetic precursor to PGE2. The structures of PGE1 (see Figure 26.5) and PGE2 are identical except that PGE2 has one more double bond than PGE1. Suggest a reasonable structure for PGE2Q:Locate the isoprene units in each of the monoterpenesLocate the isoprene units in each of the monoterpenes, sesquiterpenes, and diterpenes shown in Figure 26.6. (In some cases there are two equally correct arrangements.)Q:Identify the isoprene units in ß-caroteneIdentify the isoprene units in ß-carotene (see Figure 26.6). Which carbons are joined by a tail-to-tail link between isoprene units?Q:Write a sequence of reactions that describesWrite a sequence of reactions that describes the formation of geranylgeraniol from farnesyl pyrophosphate.Q:The structure of the bicyclic monoterpene borneolThe structure of the bicyclic monoterpene borneol is shown in Figure 26.7. Isoborneol, a stereoisomer of borneol, can be prepared in the laboratory by a two-step sequence. In the first step, borneol is oxidized to camphor by treatment with chromic acid. In the second step, camphor is reduced with sodium borohydride to a mixture of 85% isoborneol and 15% borneol. On the basis of these transformations, deduce structural formulas for isoborneol and camphor.Q:How many carbon atoms of citronellalHow many carbon atoms of citronellal would be radioactively labeled if the acetic acid used in the experiment were enriched with 14C at C-1 instead of at C-2? Identify these carbon atoms.Q:The biosynthesis of cholesterol as outlinedThe biosynthesis of cholesterol as outlined in Figure 26.10 is admittedly quite complicated. It will aid your understanding of the process if you consider the following questions:
(a) Which carbon atoms of squalene 2, 3-epoxide correspond to the doubly bonded carbons of cholesterol?
(b) Which two hydrogen atoms of squalene 2, 3-epoxide are the ones that migrate in step 3?
(c) Which methyl group of squalene 2, 3-epoxide becomes the methyl group at the C, D ring junction of cholesterol?
(d) What three methyl groups of squalene 2, 3-epoxide are lost during the conversion of lanosterol to cholesterol?Q:The biosynthetic pathway shown in Figure 26.10The biosynthetic pathway shown in Figure 26.10 was developed with the aid of isotopic labeling experiments. Which carbon atoms of cholesterol would you expect to be labeled when acetate enriched with 14C in its methyl group (14CH3COOH) is used as the carbon source?Q:Suggest a reasonable structure for vitamin D2.Suggest a reasonable structure for vitamin D2.Q:Suggest a reasonable structure for vitamin D2. 5982Suggest a reasonable structure for vitamin D2. Discuss.Q:Identify the carbon atoms expected to be labeledIdentify the carbon atoms expected to be labeled with 14C when each of the following substances is biosynthesized from acetate enriched with 14C in its methyl group:Q:The biosynthetic pathway to prostaglandinsThe biosynthetic pathway to prostaglandins leads also to a class of physiologically potent substances known as prostacyclins. Which carbon atoms of the prostacyclin shown here would you expect to be enriched in 14C if it were biosynthesized from acetate labeled with 14C in its methyl group?Q:Identify the isoprene unitsIdentify the isoprene units in each of the following naturally occurring substances: (a) Ascaridole, a naturally occurring peroxide present in chenopodium oil:Q:Cubitene is a diterpene presentCubitene is a diterpene present in the defense secretion of a species of African termite. What unusual feature characterizes the joining of isoprene units in cubitene?Q:Pyrethrins are a group of naturallyPyrethrins are a group of naturally occurring insecticidal substances found in the flowers of various plants of the chrysanthemum family. The following is the structure of a typical pyrethrin, cinerin I (exclusive of stereochemistry):Q:Cerebrosides are found in the brainCerebrosides are found in the brain and in the myelin sheath of nerve tissue. The structure of the cerebroside phrenosine isQ:Each of the following reactions has been reported in the 5989Each of the following reactions has been reported in the chemical literature and proceeds in good yield. What are the principal organic products of each reaction? In some of the exercises more than one diastereomer may be theoretically possible, but in such instances one diastereomer is either the major product or the only product. For those reactions in which one diastereomer is formed preferentially, indicate its expected stereochemistry.Q:Describe an efficient synthesisDescribe an efficient synthesis of each of the following compounds from octadecanoic (stearic) acid using any necessary organic or inorganic reagents:
(d) Icosanoic acidQ:A synthesis of triacylglycerols has been describedA synthesis of triacylglycerols has been described that begins with the substance shown.Q:The isoprenoid compound shown is a scentThe isoprenoid compound shown is a scent marker present in the urine of the red fox. Suggest a reasonable synthesis for this substance from 3-methyl-3-buten-1-ol and any necessary organic or inorganic reagents.Q:Sabinene is a monoterpene foundSabinene is a monoterpene found in the oil of citrus fruits and plants. It has been synthesized from 6-methyl-2, 5-heptanedione by the sequence that follows. Suggest reagents suitable for carrying out each of the indicated transformations.Q:Isoprene has sometimes been usedIsoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 moles of hydrogen bromide to isoprene to give 1, 3-dibromo-3-methylbutane.Q:The ionones are fragrant substances presentThe ionones are fragrant substances present in the scent of iris and are used in perfume. A mixture of a- and ß-ionone can be prepared by treatment of pseudoionone with sulfuric acid.Q:ß, Ύ-Unsaturated steroidal ketones representedß, Ύ-Unsaturated steroidal ketones represented by the partial structure shown here are readily converted in acid to their a, ß-unsaturated isomers. Write a stepwise mechanism for this reaction.Q:Consider all the isomers of C7H7Cl containingConsider all the isomers of C7H7Cl containing a benzene ring and write the structure of the one that has the weakest carbon–chlorine bond as measured by its bond dissociation energy.Q:Write the structure of the expected productWrite the structure of the expected product from the reaction of 1-chloro-2, 4-dinitrobenzene with each of the following reagents:
(d) CH3NH2Q:Write the most stable resonance structureWrite the most stable resonance structure for the cyclohexadienyl anion formed by reaction of methoxide ion with o-fluoronitrobenzene.Q:Reaction of 1, 2, 3-tribromo-5-nitrobenzeneReaction of 1, 2, 3-tribromo-5-nitrobenzene with sodium ethoxide in ethanol gave a single product, C8H7Br2NO3, in quantitative yield. Suggest a reasonable structure for this compound.Q:Write equations describing the addition–eliminationWrite equations describing the addition–elimination mechanism for the reaction of hexafluorobenzene with sodium methoxide, clearly showing the structure of the rate-determining intermediate.Q:Offer an explanation for the observationOffer an explanation for the observation that 4-chloropyridine is more reactive toward nucleophiles than 3-chloropyridine.Q:2-Bromo-1, 3-dimethylbenzene2-Bromo-1, 3-dimethylbenzene is inert to nucleophilic aromatic substitution on treatment with sodium amide in liquid ammonia. It is recovered unchanged even after extended contact with the reagent. Suggest an explanation for this lack of reactivity.Q:Two isomeric phenols are obtained in comparableTwo isomeric phenols are obtained in comparable amounts on hydrolysis of p-iodotoluene with 1 M sodium hydroxide at 300°C. Suggest reasonable structures for these two products.Q:Give the structure of the cycloaddition productGive the structure of the cycloaddition product formed when benzyne is generated in the presence of furan. (See Section 11.21, if necessary, to remind yourself of the structure of furan)Q:Write a structural formula for each of the following: (a) m-ChlorotolueneWrite a structural formula for each of the following:
(b) 2, 6-Dibromoanisole
(g) p-Bromobenzyl chloride
(d) 4, 4 -Diiodobiphenyl
(i) 1, 8-Dichloronaphthalene (e) 2-Bromo-1-chloro-4-nitrobenzene
Q:Identify the major organic productIdentify the major organic product of each of the following reactions. If two regioisomers are formed in appreciable amounts, show them both.Q:Potassium tert-butoxide reacts with halobenzenesPotassium tert-butoxide reacts with halobenzenes on heating in dimethyl sulfoxide to give tert-butyl phenyl ether.
(a) o-Fluorotoluene yields tert-butyl o-methylphenyl ether almost exclusively under these conditions. By which mechanism (addition–elimination or elimination–addition) do aryl fluorides react with potassium tert-butoxide in dimethyl sulfoxide?
(b) At 100°C, bromobenzene reacts over 20 times faster than fluorobenzene. By which mechanism do aryl bromides react?Q:Predict the products formed when eachPredict the products formed when each of the following isotopically substituted derivatives of chlorobenzene is treated with sodium amide in liquid ammonia. Estimate as quantitatively as possible the composition of the product mixture. The asterisk (*) in part (a) designates 14C, and D in part (b) is 2H.Q:Choose the compoundChoose the compound in each of the following pairs that reacts faster with sodium methoxide in methanol at 50°C:
(a) Chlorobenzene or o-chloronitrobenzene
(b) o-Chloronitrobenzene or m-chloronitrobenzene
(c) 4-Chloro-3-nitroacetophenone or 4-chloro-3-nitrotoluene
(d) 2-Fluoro-1, 3-dinitrobenzene or 1-fluoro-3, 5-dinitrobenzene
(e) 1, 4-Dibromo-2-nitrobenzene or 1-bromo-2, 4-dinitrobenzeneQ:In each of the following reactionsIn each of the following reactions, an amine or a lithium amide derivative reacts with an aryl halide. Give the structure of the expected product, and specify the mechanism by which it is formed.Q:Piperidine, the amine reactant in partsPiperidine, the amine reactant in parts (b) and (c) of the preceding problem, reacts with 1-bromonaphthalene on heating at 230°C to give a single product, compound A (C15H17N), as a noncrystallizable liquid. The same reaction using 2-bromonaphthalene yielded an isomeric product, compound B, a solid melting at 50–53°C. Mixtures of A and B were formed when either 1- or 2-bromonaphthalene was allowed to react with sodium piperidide in piperidine. Suggest reasonable structures for compounds A and B and offer an explanation for their formation under each set of reaction conditions.Q:1,2,3,4,5-Pentafluoro-6-nitrobenzene1,2,3,4,5-Pentafluoro-6-nitrobenzene reacts readily with sodium methoxide in methanol at room temperature to yield two major products, each having the molecular formula C7H3F4NO3. Suggest reasonable structures for these two compounds.Q:Predict the major organic product in each of the following 6014Predict the major organic product in each of the following reactions:Q:The hydrolysis of p-bromotoluene with aqueousThe hydrolysis of p-bromotoluene with aqueous sodium hydroxide at 300°C yields M-methylphenol and p-methylphenol in a 5:4 ratio. What is the meta–para ratio for the same reaction carried out on p-Chlorotoluene?Q:The herbicide trifluralin is preparedThe herbicide trifluralin is prepared by the following sequence of reactions. Identify compound A and deduce the structure of trifluralin.Q:Chlorbenside is a pesticide used to controlChlorbenside is a pesticide used to control red spider mites. It is prepared by the sequence shown. Identify compounds A and B in this sequence. What is the structure of chlorbenside?Q:An article in the October 1998 issueAn article in the October 1998 issue of the Journal of Chemical Education (p. 1266) describes the following reaction.Q:A method for the generation of benzyneA method for the generation of benzyne involves heating the diazonium salt from o-Aminobenzoic acid (benzenediazonium-2-carboxylate). Using curved arrows, show how this substance forms benzyne. What two inorganic compounds are formed in this reaction?Q:The compound triptycene may be prepared as shown. What is 6020The compound triptycene may be prepared as shown. What is compound A? Showing 600 – 700 of 15569 56789 > >> Join SolutionInn Study Help for 1 Million+ Textbook Solutions Learn the step-by-step answers to your textbook problems, just enter our Solution Library containing more than 1 Million+ textbooks solutions and help guides from over 1300 courses. 24/7 Online Tutors Tune up your concepts by asking our tutors any time around the clock and get prompt responses. Start Membership ×NO, THANKSTRY NOW
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