Alcohols and Phenols Questions and Answers

Section III Paragraph Single Answer Correct 4 questions 3 0 Q 33 34 Compound A on reaction with BH3 THF followed by OH H 0 gives compound X that on further reaction gives Y Compound A on reactio with H SO4 H O gives Z It gives W on reaction with CH3COO 2Hg H C followed by NaBH H SO4 H O A W 33 Formation of Z is an example of 1 BH3 THF ii OH H O i CH COO Hg H O ii NaBH4 X A electrophilic substitution reaction C electrophilic addition reaction HBr B nucleophilic addition reaction D free radical addition reaction

Boxe plea he expect major pro Box 5 please indicate the reagents necessary to complete the indicated reaction If the answer for the product is a mixture of enantiomers draw one of the enantiomers and write enantiomer If the answer is a mixture of diastereomers draw all of them Students with no printer please draw a set of numbered boxes and place answer inside 1 Br OH 1 NaH 2 EtBr DMSO 2 3

1 Both iv v 3 iii 4 v 6 In Reimer Tiemann reaction molecular weight of 26 Reimer Tiemann phenol increases by 1 28 2 29 2 ii 3 27 4 31 OH 1 a iv a v 3 iii 1 28 2 29 2 ii 4 v 3 27 4 31

169 The final products of oxidation of isopropyl alcohol are a CH3COCH HCOOH b CH CH COOH HCOOH e CH3COOH HCOOH 0 CUOL C d CH3COOH CH3CH COOH Cherchon CH

3 3dimethyl but 1 ene on reaction with aqueous mercuric acetate followed by reduction by sodium borohydride gives 2 2 dimethyl butan 1 ol 3 3 dimethyl butan 1 ol 3 3 dimethyl butan 2 ol 2 3 dimethyl butan 2 ol

4 40 The product in the given reaction is CH OH Br 3 ch Cu27 a c c CH e CH H SO4 Mon nono d methyl isocyanide Product To b d CH3 CH con Cen on anzion CM2 CH 1 CH CA NO Cna airol

96 An alcohol is not oxidised in alkaline or neutral solution b in acidic solution it is turned first to acetone and then acetic acid It is a a primary alcohol c tertiary alcohol b secondary alcohol d none of these

Identify the final product Z O H5C6 A C C CH2COOC2H5 C6H5 CH C C6H5 CH C CH3 CH3 COCH 3 COCH i NaH THF i CH COCI X KOH H O A B D Y CO C H OH CH CHO OH C6H5 CH C COOH COOH CH CH CH COCH

Which of the following alcohols undergoes dehydrations upon heating with concentrated H SO with carbocation rearrangem Select all apply Points will be deducted for incorrect answers 2 methylhexan 3 ol 2 methyl 2 phenylpropan 1 ol 2 3 dimethylpentan 2 ol 3 3 dimethylpentan 2 ol 3 methylpentan 3 ol

Consider the following statements a Methylamine is a stronger base than trimethylamine in aqueous medium b Direct nitration of aniline using nitrating mixture at 288 K gives p nitroaniline as major product c Anilinium hydrogensulphate on heating at 453 473 K gives sulphanilic acid The correct statements are a and b only b and c only a and c only a b and c

22 The best reaction sequence to convert 2 methyl 1 bromopropane into 4 methyl 2 bromopentane is A i Mg in ether ii acetaldehyde iii H H 0 iv A v HBr H O B i NaC CH in ether ii H Lindlar catalyst iii HBr no peroxide C i alcoholic KOH ii CH3COOOH iii H Pt iv HBr heat D i NaC CH in ether ii H O HgSO4 iii HBr heat B

59 Which alcohol produces turbidity with lucas reagent most slowly 1 2 Butanol 2 t Butyl alcohol 3 Isobutyl alcohol 4 Diphenyl carbinol 59 2 c Cfs f LL ENTHUSE LEADER ACHIEVER ALPHA PLUS SPARK CRASH COURSE ge 16 56 Space for D

Use the information below for Part H Parti For the reaction 21 S 08 2SO4 1 It was found that under a given set of reactant concentrations it took 7 seconds for the iodine 1 concentration to change by 4x10 5 M Part H Calculating average rate Calculate the average rate of iodine production over this time period Give your answer to 3 significant figures View Available Hint s d 1 dt AEO mol L 1 S 1

38 Write the IUPAC name of H CH C CH CH CH C CH a b 1 OH 6 6 dibromoheptan 2 ol 2 2 dibromoheptan 6 ol c 6 6 dibromoheptan 1 ol d none of these a T S P b S T P 39 When phenol is treated with CHCl3 and NaOH the product formed in a Benzaldehyde b Salicylaldehyde c salicyclic acid d benzoic acid 40 Order of esterification of alcohols is C P S T d P T S Br 41 When ether is exposed in air for sometime an explosive substance produced is a Peroxide b TNT c Oxide d super oxides 42 Lucas test is used for distinction of a Alcohols b Phenols c alkyl halides d aldehydes 43 IUPAC name of the compound CH CH CH CH CH is T OH CH3 Br a 4 methylpentene 2 ol b 2 methylpentanol 4 c 4 4 dimethyl butan 2 ol d 4 methylpentan 2 ol

18 What is the outcome of the reaction acetic anhydride with CH3OH a acetic acid and methyl ethanoate formic and acetic acids b c only ethanol d acetic acid and ethyl methanoate

What is the product of this reaction O H HO OH OH 1 BH3THF 2 H O NaOH

Which should be more soluble in NH3 CH3CH CH CH3 choice in terms of attractive forces or HOCH CH OH Explain your

A particular liquor is 28 0 ethanol CH3CH OH by volume Calculate the concentration of ethanol in molality The density of ethanol is 0 789 g mL the density of water is 0 998 g mL assume the volumes are additive Your Answer m m

What is the starting material for the reaction below O II OI SO IV 11 NaOH OH IV

What starting material with these reagents will result in 3 3 4 4 tetrabromoheptan 1 PBr3 2 NaCEC 3 Br excess O O O OH OH OH OH Br Br Br Br

What is the product in the following reaction OH O O CN CN OH 3 CN 1 SOCI 2 NaCN

Identify bond line structures for constitutional isomers with a molecular formula of C4H10O I and II II and III III and IV IV and V II and IV H 1 OH III OH OH IV V OH

1 2 3 alcohols can be differentiated with Br water Cu 573 K Libermann test

vi What major product s would you expect from the following reactions Show the reaction mechanim 1 Acid catalyzed dehydration of alcohols 2 Acid catalyzed addition of alcohols to alkenes 3 Acid catalyzed ring opening

What is the product of the following reaction NaOCH3 S CH OH OH lo I O III OIV 11 OH IV

50 I CH CH NGHI 2 8 0 8 H SO4 140 C 1 egiv e synthesis for only

N Acylation and O Acylation OH O O O 0 OH 0 NH OH O HP 0 00 0 N ZH OH OH

p alkynylalcohols Starting with 3 5 hexadiyn 1 ol select reagents from the table below that should be used to synthesize 1 8 octanediol HO HO 3 5 hexadiyn 1 ol The reaction may require more than one step if so write the letters in the order that they are used e g abc If two or more ways conversion to the same product are possible show only one of them Omit steps that are part of the workup procedure 1 8 octanediol Reagents available a NaNH NH f TBDMS Cl b H Pt g Bu4N F c H Lindlar catalyst h Na NH3 liq d PCC i ethylene oxide e H O

nn Arrow pushing Instructions H C CH H Ethylene glycol a common organic solvent and automotive antifreeze agent is synthesized by reaction of ethylene oxide in water with a sulfuric acid catalyst Write a detailed mechanism for this synthesis shown above Then draw curved arrows that depict electron reorganization for Step 1 of the mechanism shown below Unless specified otherwise do not count proton transfers when counting steps The starting materials of this step are provided XI H o H H H SO4 HOCH CH OH

HO OH Ethylene oxide is the starting material for the synthesis of 1 4 dioxane Write a detailed mechanism for this synthesis shown above Then draw curved arrows that depict electron reorganization for Step 2 of the mechanism shown below Unless specified otherwise do not count proton transfers when counting steps The starting materials of this step provided Arrow pushing Instructions nn XII H C O H H C

Draw the structural formula of the major product of the reaction of S 2 2 3 trimethyloxirane with MeOH H Use the wedge hash bond tools to indicate stereochemistry where it exists Include H atoms at chiral centers only If a group is achiral do not use wedged or hashed bonds on it References Y

Himung C6H5 product 1 product 2 C6H5 H This equation shows the reaction of trans 2 3 diphenyloxirane with hydrogen chloride to form 2 chloro 1 2 diphenylethanol 2S 3R Submit Ar 2R 3S 3S 4R 3R 4S 2S 3S 2R 3R 3S 4S How many total stereoisomers are possible for 2 chloro 1 2 diphenylethanol 3R 4R 1R 2R 1S 2S 1R 2S HCI Given that opening of the epoxide ring in this reaction is stereoselective provide the names of the only two isomeric products formed using IUPAC guidelines C6H5 C CeHs OH CI 2 chloro 1 2 diphenylethanol 2 chloro 1 2 diphenylethanol Try Another Version 2 item attempts remaining

4 What is the product of the following reaction OH 1 NaH 2 propyl iodide A B C D O

What is are the major substitution products for the following reaction A B C E Product 1 is major H3CO Product 2 is major D A mixture of 1 and 5 would be major A 1 1 mixture of 2 and 3 would be major A mixture of 4 and 5 would be major OH OCH3 conc H SO4 CH3OH OCH3 Product s OH HO

Which of these is inaccurate CI DIBAIH DMSO 0 THF Zn HCI AICI OCHS 1 CH Br Mg ether 2 H O H CH

11 15 Propose an efficient synthesis for each of the following transformations a b OH OH y

Draw the alcohol needed to produce the alkyl chloride under the conditions shown Draw Alcohol Reactant CI SOCI2 pyridine

Which alcohol would undergo a dehydration reaction the fastest when treated with concentrated H2SO4 A A B B C C D D E E OH OH B OH OH LL F OH

Give the major product in each of the following HO CH3 H3C CH3 CH3 H SO4 dehydration

True False The following compound is phenol OH O True O False

A OA OB Pick the Grignard reagent and an epoxide to make this alcohol OC OD MgBr B MgBr C OH X D

Draw the product of this reaction Ignore inorganic byproducts Br2 2 equiv Select to Draw I I I I I I I I I I

Mechanisms Provide a complete stepwise mechanism to explain each of the following transformations Be certain to include ALL intermediate structures and electron shift arrows that clearly indicate the electron transitions and bond changes that convert one structure to the next a b Br HO OH H O EtOAc H SO4 H O at

How many hydrogen atoms are present in the following compound a 10 O b 9 Oc 11 d 12 OH

the final product 10 What Is 2 3 dimethyl pentam 1 01 w Nay Cr 07 1 50 4 methanol CH3OH in acid name product

1 12 pts Provide the structure s of the expected major organic product s Unless mentioned otherwise you can assume that all reagents are present in one mole Show stereochemistry where needed and write NR if there is no reaction non hindered Base NaOC H5 C H5OH aifsev a O H Br b HC C CH3 heat nun hind 1 CH Li THF 2 3 HO C Hs

Which set of reagents would be suitable for the completion of the following flow chart OH xx A PCC B H CRO4 THF 2 NaOH H O2 OH C 1 Hg OAC 2 H O 2 NaBH4 OI H II C III G IV J V B OI E II D III A IV J V A IV E H3PO4 heat F KOtbu G 1 LiAlH4 2 H3O H 1 NaBH4 2 H3O J 1 Ph MgBr ether 2 H3O I F II D III B IV J V A OH I F II D III A IV J V B D 1 BH3

Which of the following alcohols can give carboxylic acid by Jones oxidation O OH OH OH OH

Which process will give a secondary alcohol but 2 ene hydroboration Benzaldehyde NaBH4 followed by H3O Propan 1 ol NaOH 7 mothed pron 2 and pomorsuration demorcuration

write the product prepared with butanote of 1 1 dimethylethyl i dont need the phenyl one HO