Skip to main contentcloseHomework Help is Here – Start Your Trial Now!arrow_forwardSEARCHHomework help starts here!ASK AN EXPERTASKScienceChemistryOH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C° H3C d-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H¯ adds to the sp² carbon with the most hydrogens to yield the most stab ocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. void the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with se phydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an anomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. w curved arrows to show the movement of electrons in this step of the mechanism. row-pushing Instructions AcO-Hg-OAc AcO-Hg OACOH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C° H3C d-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H¯ adds to the sp² carbon with the most hydrogens to yield the most stab ocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. void the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with se phydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an anomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. w curved arrows to show the movement of electrons in this step of the mechanism. row-pushing Instructions AcO-Hg-OAc AcO-Hg OACBUYChemistry 10th EditionISBN: 9781305957404Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher: Cengage Learningexpand_less1 Chemical Foundations2 Atoms, Molecules, And Ions3 Stoichiometry4 Types Of Chemical Reactions And Solution Stoichiometry5 Gases6 Thermochemistry7 Atomic Structure And Periodicity8 Bonding: General Concepts9 Covalent Bonding: Orbitals10 Liquids And Solids11 Properties Of Solutions12 Chemical Kinetics13 Chemical Equilibrium14 Acids And Bases15 Acid-base Equilibria16 Solubility And Complex Ion Equilibria17 Spontaneity, Entropy, And Free Energy18 Electrochemistry19 The Nucleus: A Chemist's View20 The Representative Elements21 Transition Metals And Coordination Chemistry22 Organic And Biological Moleculesexpand_moreChapter Questionsexpand_moreProblem 1RQProblem 2RQProblem 3RQProblem 4RQProblem 5RQProblem 6RQProblem 7RQProblem 8RQProblem 9RQProblem 10RQProblem 1ALQProblem 2ALQProblem 3ALQProblem 4ALQProblem 5ALQProblem 6ALQProblem 7ALQProblem 8ALQProblem 9ALQProblem 10ALQProblem 11ALQProblem 14ALQProblem 15ALQProblem 16ALQProblem 17ALQProblem 18ALQProblem 19QProblem 20QProblem 21QProblem 22QProblem 23QProblem 24QProblem 25QProblem 26QProblem 28QProblem 29QProblem 30QProblem 31EProblem 32EProblem 33EProblem 34EProblem 35EProblem 36EProblem 37EProblem 38EProblem 39EProblem 40EProblem 41EProblem 42EProblem 43EProblem 44EProblem 45EProblem 46EProblem 47EProblem 48EProblem 49EProblem 50EProblem 51EProblem 52EProblem 53EProblem 54EProblem 55EProblem 56EProblem 57EProblem 58EProblem 59EProblem 60EProblem 61EProblem 62EProblem 63EProblem 64EProblem 65EProblem 66EProblem 67EProblem 68EProblem 69EProblem 70EProblem 71EProblem 72EProblem 73EProblem 74EProblem 75EProblem 76EProblem 77EProblem 78EProblem 79EProblem 80EProblem 81EProblem 82EProblem 83EProblem 84EProblem 85EProblem 86EProblem 87EProblem 88EProblem 89EProblem 90EProblem 91EProblem 92EProblem 93AEProblem 94AEProblem 95AEProblem 96AEProblem 97AEProblem 98AEProblem 99AEProblem 100AEProblem 101AEProblem 102AEProblem 103AEProblem 104AEProblem 105AEProblem 106AEProblem 107AEProblem 108AEProblem 109AEProblem 110AEProblem 111CWPProblem 112CWPProblem 113CWPProblem 114CWPProblem 115CWPProblem 116CWPProblem 117CPProblem 118CPProblem 119CPProblem 120CPProblem 121CPProblem 122CPProblem 123CPProblem 124CPProblem 125CPformat_list_bulletedSee similar textbooks
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Q: Hydrates, in which two -OH groups are connected to the same carbon, are not favorable except in a…A: 1. Hydration of carbonyl compounds : Aldehydes and ketones react with water in presence of an…Q: Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by…A: ->In oxymercuration-demercuration overall morkovnikov addition of H2O takes place.Q: Draw a structural formula for the major product of the reaction shown. CHa CHICHCH=CH₂ Cl₂ H₂O Show…A: Q: H3C CH3 CH3 OHA: Greater the substitution higher will be the stability of akeneQ: Draw a structural formula for the major product of the reaction shown. H3C Cl2 H3C H20 • Show…A: Q: 5.Synthesis. Make the following products from a suitable cyclic alkene starting material. Look at…A: Q: #2 Draw the product of the reaction shown below. Use wedge and dash bonds to indicate…A: Q: 4. Draw the correct structure for each of the following c A) 2R-bromo-3S-pentanol B) 3-methyl-2E,…A: Q: Ph CH3 CH3 The Wolff-Kishner reaction involves the reaction of an aldehyde/ketone with hydrazine in…A: In the given reaction, reduction of ketone to alkane takes place in the presence of hydrazine. The…Q: CH3 CH3 1. ВНз, THF 2. NaOH, H,0, H,О2 H3C HO °CH2 H3C Alkenes can be hydrated via the addition of…A: Q: Draw a structural formula for the product formed upon hydroboration/oxidation of the alkene below.…A: It is an example of hydroboration reaction Here we are required to predict the product of the…Q: Draw the structure of the major organic product of the reaction. CI 1. LIAIH4, ether 2. H₂OA: LiAlH4 is the strongest reducing agent.Which reduce the acyl halide to the primary alcohol.Thus the…Q: Write the following reactions by explaining the mechanism; Explain the stereochemistry at each step.…A: Carbonyl centre is electrophilic in nature so favours nucleophilic attack .Q: OH 1. Hg(OAc)2. H20 2. NABH,A: Product can be synthesized from the reaction of an alkene with Hg(OAc)2 followed by reduction with…Q: Which alcohol is formed from the acid-catalyzed hydration of the following alkene? H CH3 H,0 H2SO4…A: Q: g. h. j. н п 1. ВН3 2. NaOH, H2O2, но 1. ВН3 2. NaOH, H2O2, но ОНA: Q: Consider the following mechanism of reaction: CH CH CH;C-CH, + H-CI CH;CCH; + CI: → CH;CCH,…A: The nucleophile is the nucleus loving. This means they have enough electron to donate.Q: ose the best starting alkyne for the reaction in the imA: Various organic compounds are converted to other organic compounds with the help of some reagents.Q: Draw a structural formula for the major organic product of the follo i -CH=CHCOH + Cl₂ CH3A: GIven that, the reaction is:Q: d. HN OH 1. N=C=S 2. H₂SO4, H₂O (2 products)A: Q: Draw the two major products of this reaction. Use wedge and dash bonds to indicate stereochemistry…A: Q: Draw a structural formula for the major product of the reaction shown. CH3CH2CH=CHCH2CH3 Cl2 H20 •…A: The alkene undergo chlorination reaction by the formation of chloronium ion . Now there are two…Q: (0) H20, H2SO4 (Р) (T) HBr CH;OH HSO4 CH3 1. ВН3THF 2. НО, Н-О2. НС 2 МСРВА (S) (Q) Br2, H20 (R)A: Q: Provide the structure of the missing products or reactants. Show the relevant stereochemistry if…A: To find the structure of the products formed in the reaction.Q: Give the starting alkene and any other reagents needed to selectively make the following compounds…A: 4. We have to give the starting alkenes and the reagents that selectively give those desired…Q: How many stereoisomers are formed in the reaction below? Please note: both alkenes will react under…A: Q: Name the alkene. Be sure to indicate stereochemistry and use hyphens (-) not endashes (–). The…A: The structure for given molecule is represented as follows:Q: 1. NaNH2 2. BrA: Given reaction: We have to find the products of the reaction.Q: which Com the conjugate addition of 10 NC D CNA: The objective of the question is to give the product of the given reaction.Q: OH H₂SO4 HỌC–CH2–CH2CH3 HỌC=CH–CH2CH3 H₂O Acid-catalyzed dehydration of 1-butanol yields 1-butene as…A: The acid catalysed dehydration of alcohol has 3 steps- 1- protonation of OH group 2- removal of…Q: Ph CH3 CH3 The Wolff-Kishner reaction involves the reaction of an aldehyde/ketone with hydrazine in…A: Q: suged to rearangenert 8) Dehydration of an unknown alcohol with concentrate@ H2SO4 results in the…A: Note : Alcohols undergo acid catalyzed rearrangement. ( see below).Q: Draw a structural formula for the major organic anion formed when 2- ethylbutanal is reacted with…A: tollens and the dichromate are the oxidising agent . in presence of thess reactants the aldehyde…Q: Fill in the missing reactant, reagent and products. Indicate stereochemistry if necessary. Unless…A: Q: /hich of the following reaction sequences would you use to convert 1- methylcyclohexene to the…A: Hydroboration oxidation reaction is syn addition reaction means hydrogen and hydroxyl both group add…QuestionTranscribed Image Text:OH 1. Hg(OAc)2, H20 2. NaBH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp2 carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AcO-Hg-OAc AcO-Hg OAc Expert SolutionThis question has been solved!Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.This is a popular solutionSee solutionCheck out a sample Q&A hereStep 1:: Reaction VIEW Step 2:: Mechanism VIEW
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Chemistryarrow_forwardDraw a structural formula for the major product of the reaction shown. Cl₂ H₂O Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. If the reaction produces a racemic mixture, just draw one stereoisomer. 8 Sn [F ChemDoodleⓇarrow_forwardA common alkene starting material is shown below. Predict the major product for each reaction. Ignore any inorganic byproducts. I I Select to Select to Draw I Draw I HBr Cl₂ H₂O 1. BH3-THF 2. H2O2, NaOH nd 1.03 2. (CH3)2Sarrow_forward
An alkene having the molecular formula C6H₁2 is treated sequentially with ozone (03) and zinc/acetic acid to give the product/s shown. O Draw a structural formula for the alkene. H3C 1 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. + ▾ CH3 will n [F ChemDoodleⓇ 16arrow_forward5. Even with excess cyanide present, only one equivalent will react with the following dibromoalkane. To which carbon with the cyanide add? Predict the product and explain your choice. Br H₂C H₂C CH3 Br CN DMSOarrow_forwardIn this chapter, we studied the mechanism of the acid-catalyzed hydration of an alkene. The reverse of this reaction is the acid-catalyzed dehydration of an alcohol. OH H,SO, CH,-CH-CH, CH-CH=CH, + H,O 2-Propanol (Isopropyl alcohol) Propene Propose a mechanism for the acid-catalyzed dehydration of 2-propanol to propene.arrow_forward
Kelerences Keview topic Draw a structural formula for the major product of the reaction shown. Cl2 H20 CH;CH2CH;CH=CHz • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. 2reg 2reg M) ots 2reg pts 2req 1 pts 2req 1 pts 2reg ...1 pts ChemDoodle Previous Next> Save and Exit APR tv MacBook Air 80 DII DD F3 F4 FS F6 F7 F8 F10 F1 F12 #3 $ & + 3 4 6. 7 8 %3D dele E Y | { } P [ F G H. J K C V N M ? .. .. * C0 Barrow_forward9.arrow_forwardDraw a structural formula for the major organic product of the reaction shown below. S. 10 + 2 + ether -CuLi H3O • You do not have to consider stereochemistry. √n [F ? ChemDoodlearrow_forward
A. In the following reaction, the alkene is acting as a/n + B. In the following reaction, water is acting as a/n CCH3 + H20: HOCHCH3 + H3oarrow_forwardAn alkene having the molecular formula C,H12 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. CH3CH2CH,CH½CH2CH Draw a structural formula for the alkene. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. P opy aste Previous Nextarrow_forwardAdd reactants, reagents and products. Include the stereochemistry if necessary. Unless otherwise stated, assume the reagents are in excess.arrow_forward
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BUYChemistry 10th EditionISBN: 9781305957404Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher: Cengage Learningexpand_less1 Chemical Foundations2 Atoms, Molecules, And Ions3 Stoichiometry4 Types Of Chemical Reactions And Solution Stoichiometry5 Gases6 Thermochemistry7 Atomic Structure And Periodicity8 Bonding: General Concepts9 Covalent Bonding: Orbitals10 Liquids And Solids11 Properties Of Solutions12 Chemical Kinetics13 Chemical Equilibrium14 Acids And Bases15 Acid-base Equilibria16 Solubility And Complex Ion Equilibria17 Spontaneity, Entropy, And Free Energy18 Electrochemistry19 The Nucleus: A Chemist's View20 The Representative Elements21 Transition Metals And Coordination Chemistry22 Organic And Biological Moleculesexpand_moreChapter Questionsexpand_moreProblem 1RQProblem 2RQProblem 3RQProblem 4RQProblem 5RQProblem 6RQProblem 7RQProblem 8RQProblem 9RQProblem 10RQProblem 1ALQProblem 2ALQProblem 3ALQProblem 4ALQProblem 5ALQProblem 6ALQProblem 7ALQProblem 8ALQProblem 9ALQProblem 10ALQProblem 11ALQProblem 14ALQProblem 15ALQProblem 16ALQProblem 17ALQProblem 18ALQProblem 19QProblem 20QProblem 21QProblem 22QProblem 23QProblem 24QProblem 25QProblem 26QProblem 28QProblem 29QProblem 30QProblem 31EProblem 32EProblem 33EProblem 34EProblem 35EProblem 36EProblem 37EProblem 38EProblem 39EProblem 40EProblem 41EProblem 42EProblem 43EProblem 44EProblem 45EProblem 46EProblem 47EProblem 48EProblem 49EProblem 50EProblem 51EProblem 52EProblem 53EProblem 54EProblem 55EProblem 56EProblem 57EProblem 58EProblem 59EProblem 60EProblem 61EProblem 62EProblem 63EProblem 64EProblem 65EProblem 66EProblem 67EProblem 68EProblem 69EProblem 70EProblem 71EProblem 72EProblem 73EProblem 74EProblem 75EProblem 76EProblem 77EProblem 78EProblem 79EProblem 80EProblem 81EProblem 82EProblem 83EProblem 84EProblem 85EProblem 86EProblem 87EProblem 88EProblem 89EProblem 90EProblem 91EProblem 92EProblem 93AEProblem 94AEProblem 95AEProblem 96AEProblem 97AEProblem 98AEProblem 99AEProblem 100AEProblem 101AEProblem 102AEProblem 103AEProblem 104AEProblem 105AEProblem 106AEProblem 107AEProblem 108AEProblem 109AEProblem 110AEProblem 111CWPProblem 112CWPProblem 113CWPProblem 114CWPProblem 115CWPProblem 116CWPProblem 117CPProblem 118CPProblem 119CPProblem 120CPProblem 121CPProblem 122CPProblem 123CPProblem 124CPProblem 125CPformat_list_bulletedSee similar textbooks
Q: Hydrates, in which two -OH groups are connected to the same carbon, are not favorable except in a…A: 1. Hydration of carbonyl compounds : Aldehydes and ketones react with water in presence of an…Q: Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by…A: ->In oxymercuration-demercuration overall morkovnikov addition of H2O takes place.Q: Draw a structural formula for the major product of the reaction shown. CHa CHICHCH=CH₂ Cl₂ H₂O Show…A: Q: H3C CH3 CH3 OHA: Greater the substitution higher will be the stability of akeneQ: Draw a structural formula for the major product of the reaction shown. H3C Cl2 H3C H20 • Show…A: Q: 5.Synthesis. Make the following products from a suitable cyclic alkene starting material. Look at…A: Q: #2 Draw the product of the reaction shown below. Use wedge and dash bonds to indicate…A: Q: 4. Draw the correct structure for each of the following c A) 2R-bromo-3S-pentanol B) 3-methyl-2E,…A: Q: Ph CH3 CH3 The Wolff-Kishner reaction involves the reaction of an aldehyde/ketone with hydrazine in…A: In the given reaction, reduction of ketone to alkane takes place in the presence of hydrazine. The…Q: CH3 CH3 1. ВНз, THF 2. NaOH, H,0, H,О2 H3C HO °CH2 H3C Alkenes can be hydrated via the addition of…A: Q: Draw a structural formula for the product formed upon hydroboration/oxidation of the alkene below.…A: It is an example of hydroboration reaction Here we are required to predict the product of the…Q: Draw the structure of the major organic product of the reaction. CI 1. LIAIH4, ether 2. H₂OA: LiAlH4 is the strongest reducing agent.Which reduce the acyl halide to the primary alcohol.Thus the…Q: Write the following reactions by explaining the mechanism; Explain the stereochemistry at each step.…A: Carbonyl centre is electrophilic in nature so favours nucleophilic attack .Q: OH 1. Hg(OAc)2. H20 2. NABH,A: Product can be synthesized from the reaction of an alkene with Hg(OAc)2 followed by reduction with…Q: Which alcohol is formed from the acid-catalyzed hydration of the following alkene? H CH3 H,0 H2SO4…A: Q: g. h. j. н п 1. ВН3 2. NaOH, H2O2, но 1. ВН3 2. NaOH, H2O2, но ОНA: Q: Consider the following mechanism of reaction: CH CH CH;C-CH, + H-CI CH;CCH; + CI: → CH;CCH,…A: The nucleophile is the nucleus loving. This means they have enough electron to donate.Q: ose the best starting alkyne for the reaction in the imA: Various organic compounds are converted to other organic compounds with the help of some reagents.Q: Draw a structural formula for the major organic product of the follo i -CH=CHCOH + Cl₂ CH3A: GIven that, the reaction is:Q: d. HN OH 1. N=C=S 2. H₂SO4, H₂O (2 products)A: Q: Draw the two major products of this reaction. Use wedge and dash bonds to indicate stereochemistry…A: Q: Draw a structural formula for the major product of the reaction shown. CH3CH2CH=CHCH2CH3 Cl2 H20 •…A: The alkene undergo chlorination reaction by the formation of chloronium ion . Now there are two…Q: (0) H20, H2SO4 (Р) (T) HBr CH;OH HSO4 CH3 1. ВН3THF 2. НО, Н-О2. НС 2 МСРВА (S) (Q) Br2, H20 (R)A: Q: Provide the structure of the missing products or reactants. Show the relevant stereochemistry if…A: To find the structure of the products formed in the reaction.Q: Give the starting alkene and any other reagents needed to selectively make the following compounds…A: 4. We have to give the starting alkenes and the reagents that selectively give those desired…Q: How many stereoisomers are formed in the reaction below? Please note: both alkenes will react under…A: Q: Name the alkene. Be sure to indicate stereochemistry and use hyphens (-) not endashes (–). The…A: The structure for given molecule is represented as follows:Q: 1. NaNH2 2. BrA: Given reaction: We have to find the products of the reaction.Q: which Com the conjugate addition of 10 NC D CNA: The objective of the question is to give the product of the given reaction.Q: OH H₂SO4 HỌC–CH2–CH2CH3 HỌC=CH–CH2CH3 H₂O Acid-catalyzed dehydration of 1-butanol yields 1-butene as…A: The acid catalysed dehydration of alcohol has 3 steps- 1- protonation of OH group 2- removal of…Q: Ph CH3 CH3 The Wolff-Kishner reaction involves the reaction of an aldehyde/ketone with hydrazine in…A: Q: suged to rearangenert 8) Dehydration of an unknown alcohol with concentrate@ H2SO4 results in the…A: Note : Alcohols undergo acid catalyzed rearrangement. ( see below).Q: Draw a structural formula for the major organic anion formed when 2- ethylbutanal is reacted with…A: tollens and the dichromate are the oxidising agent . in presence of thess reactants the aldehyde…Q: Fill in the missing reactant, reagent and products. Indicate stereochemistry if necessary. Unless…A: Q: /hich of the following reaction sequences would you use to convert 1- methylcyclohexene to the…A: Hydroboration oxidation reaction is syn addition reaction means hydrogen and hydroxyl both group add…Question
Transcribed Image Text:OH 1. Hg(OAc)2, H20 2. NaBH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp2 carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AcO-Hg-OAc AcO-Hg OAc 
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ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
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ASK AN EXPERTASKScienceChemistryOH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C° H3C d-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H¯ adds to the sp² carbon with the most hydrogens to yield the most stab ocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. void the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with se phydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an anomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. w curved arrows to show the movement of electrons in this step of the mechanism. row-pushing Instructions AcO-Hg-OAc AcO-Hg OACOH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C° H3C d-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H¯ adds to the sp² carbon with the most hydrogens to yield the most stab ocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. void the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with se phydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an anomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. w curved arrows to show the movement of electrons in this step of the mechanism. row-pushing Instructions AcO-Hg-OAc AcO-Hg OAC