ALCOHOLS AND PHENOLS; ETHERS AND EPOXIDES; THIOLS AND SULFIDES

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1 ALCHLS AND PHENLS; ETHERS AND EPXIDES; THILS AND SULFIDES A STUDENT SHULD BE ABLE T: 1. Give the IUPAC name when given the structure, and draw the structure given the name of open-chain and monocyclic alcohols, phenols and ethers (alcohol nomenclature was first covered in Module 4; ethers are named as alkoxyalkanes). Also, draw the structure when given the common name, and name when given the structure of ethylene glycol, tetrahydrofuran, and simple alcohols and ethers containing any of the alkyl groups listed in the objectives for Module 4, rganic Chemistry I. Also, draw examples of, and identify the functional groups in, thiols, thioethers, and disulfides. Note: thiols, RSH (alcohols, RH) thioethers RSR (ethers RR) disulfides RSSR (peroxides RR) sulfoxides RSR (ketones RCR) 2. Predict relative physical properties, including boiling points and relative solubilities, of alcohols, ethers, sulfur-containing compounds, and other compounds. The principles involved were covered in previous modules. Also, be able to predict the relative acidities of phenols and alcohols. 3. Given the starting materials and reaction conditions, predict the products of the following reactions involving alcohols and ethers. Preparations of alcohols: Substitution reactions: S N 1, S N 2 (see Module 7, rganic Chemistry I) Acid-catalyzed hydration of alkenes (see Module 9, rganic Chemistry I) Hydroboration-oxidation (hydroboration is a syn addition; replacement of boron by H in the oxidation step occurs with retention, and the overall process is also a net syn addition) (see Module 9, rganic Chemistry I) xymercuration-demercuration (see Module 9, rganic Chemistry I) Reduction of ketones, aldehydes, carboxylic acids, and esters with LiAlH 4 (LAH) and of ketones and aldehydes with NaBH 4. Reactions of Grignard reagents and alkyllithium reagents with acids, ethylene oxide, ketones, aldehydes, and esters. (Including the synthesis of the Grignard reagent via alkyl and aryl halides reacting with Mg in the presence of ether) Grignard and alkyllithium reagents react with: Formaldehyde to give 1 alcohols with one more carbon atom than the starting material Ethylene oxide to give 1 alcohols with two more C s than the starting material Aldehydes to give 2 alcohols Ketones and esters to give 3 alcohols

2 Reactions of alcohols: Acid-base reactions involving alcohols and their conjugate bases. The order of relative acidity is: mineral acids > carboxylic acids > water > alcohols > terminal alkynes > ammonia and amines > alkanes. xidation of 1 and 2 alcohols using pyridinium chlorochromate (PCC); and of 1 and 2 alcohols and aldehydes using chromic acid. Formation of sulfonate (e.g., tosylate) esters (see Module 7, rganic Chemistry I) Formation of alkyl halides from alcohols using hydrogen halides, PBr 3, and SCl 2 Preparation of ethers: The Williamson synthesis of ethers (the S N 2 reaction of an alkoxide with an alkyl halide). Note that methyl and 1 alkyl halides give the ether as the product; 2 and 3 halides give alkenes by an E2 reaction. 4. Using any of the above reactions, propose syntheses of compounds that can be made using alcohols as starting materials or intermediates. As always, synthesis problems may require any reaction that you have studied in the course so far. 5. Propose mechanisms, and predict and explain experimental results using your knowledge of mechanism. Important reactions include: Hydration and dehydration (covered in previous modules). Reaction of alcohols with hydrogen halides. Hydride addition to a carbonyl rganometallic addition to a carbonyl

3 To best prepare for this module, please work Chapters 13 and 14 Skill Builder problems in the textbook. A STUDENT WH HAS MASTERED THE BJECTIVES N THE PREVIUS PAGE SHULD BE ABLE T SLVE THE FLLWING PRBLEMS AND RELATED NES: 1.1 Name each of the following compounds. a) HCH2CH(CH3)2 b) CH3CH2 H CH(CH 3)2 c) CH3CH2CH(CH3)C(H)CH2CH3 d) H H 1.2 Draw the structure of each of the following compounds. a) 2-methoxy-5-methylheptane b) 3-tert-butyl-4-methylcyclohexanol c) tetrahydrofuran d) isopropoxycyclopentane e) 2-bromophenol f) 2,4,6-trimethoxyphenol 1.3 Give an example of the following compounds. (Be specific; do not use R) a) a disulfide b) a thiol 2.1 Which of the following compounds has the lowest boiling point? A. CH 3 (CH 2 ) 4 CH 2 H B. CH 3 (CH 2 ) 2 CH(H)CH 2 CH 3 C. (CH 3 CH 2 CH 2 ) 2 D. (CH 3 ) 2 CHCH(CH 3 ) 2

4 2.2 Which of the following compounds is the least soluble in water? A. CH 3 CH 2 CH B. CH 3 CH 2 CH 2 H C. CH 3 CH 2 CNa D. CH 3 CH 2 CH 2 Cl 2.3 a) Which of the following is the strongest acid? b) Which is the strongest base? A. H B. H C. - D a) Which of the following is the strongest acid? b) Which is the strongest base? A. H B. - C. CH3 H D. CH3-3.1 Predict the products of the reactions given below (if any). a) H + NH > b) - + CH 3C CH ----> c) (CH 3 ) 3 C + CH 3 NH > d) H + CH 3 CH 2 H -----> e) (CH 3 ) 3 C + CH 3 C CH -----> f) H + CH 3 CH 2 CH > g) CH 3 NH + CH 3 CH 2 H -----> 3.2 Predict the organic product(s) of the reactions given below, including stereochemistry whenever appropriate. a) H + PBr > b) BH3, THF H 2 2, H > >

5 c) H3P4 =CH2 + H > d) (CH 3 ) 2 CH CH 2 H + Ts-Cl + Base e) (CH 3 ) 2 CH + CH 3 CH 2 CH 2 Br -----> CH3 f) CH > Br g) Hg(Ac) 2, H2 NaBH 4, H > > 3.3 Predict the product(s) of each of the following reactions (if any). a) Br b) H-C Li > ether CCH3 c) CH2CH2H NaBH > C5H5NH + Cr3Cl > d) MgBr + C-H H > > e) CH2Li + CH3H ---> f) (CH 3 ) 2 CHMgBr + CH 3 C-H ---> g) MgBr + CH3C-CH3 H 3 + h) CH 3 CH 2 MgBr + H-C-H ---> > i) CH2MgBr + C-CH3 H > > H > >

6 4.1 Propose a synthesis of each of the compounds shown, from the given starting materials and any other needed reagent a) b) from CH3CH2H and H c) from CH2H =CH2 CH3 d) from H =CH2 4.2 Propose syntheses of each of the following compounds, from the given starting material and any other needed reagents. a) CH2H from C-H b) CH 3 CCH 3 from CH 3 CH=CH 2 c) H CHCH 3 from Br

7 d) CH2CH2CH2H from CH2H e) CH2CH2C2H from CH3 f) 5. Propose a mechanism for each of the following reactions. H2S 4, heat a) CH=CH2 + H > CH 2 CH3 H H 2 S 4 b) (CH 3 ) 3 CCHHCH > H 2 + (CH 3 ) 2 C=C(CH 3 ) 2 c)

8 SLUTINS T SAMPLE PRBLEMS: 1.1 Names of the compounds shown: a) isobutyl alcohol or 2-methyl-1-propanol b) cis-3-ethoxycyclohexanol c) 3-ethyl-2,4-dimethyl-3-hexanol d) ethylene glycol or 1,2-ethanediol e) 3,5-dimethylphenol f) 3-nitrophenol 1.2 Structures of the compounds named: a) 2-methoxy-5-methylheptane b) 3-tert-butyl-4-methylcyclohexano CH3CHCH 2CH2CHCH 2CH3 CH3 CH 3 (CH3)3C H3C H c) tetrahydrofuran d) isopropoxycyclopentane -CH(CH3)2 e) 2-bromophenol f) 2,4,6-trimethoxyphenol 1.3 a) a disulfide: CH 3 S-SCH 2 CH 3 b) a thiol: (CH 3 ) 2 CHSH 2.1 D 2.2 D 2.3 a) B b) C 2.4 a) A b) D 3.1 Predict the products a) b) c) (CH 3 ) 3 C + CH 3 NH 2 (CH 3 ) 3 CH + CH 3 NH d) H + CH 3 CH 2 H no reaction (A small amount of H 2 + CH 3 CH 2 - will form, but the equilibrium strongly favors the reactants)

9 e) (CH 3 ) 3 C + CH 3 C CH (CH 3 ) 3 CH + CH 3 C C 3.1 f) H + CH 3 CH 2 CH 3 no reaction g) CH 3 NH + CH 3 CH 2 H CH 3 NH 2 + CH 3 CH Predict the product(s) of the reactions given below, including stereochemistry whenever appropriate. a) H + PBr > Br b) c) BH3, THF H 22, H > > H 3P4 =CH2 + H > H CH3 H H + enant. d) (CH 3 ) 2 CH CH 2 H + Ts-Cl + Base (CH 3 ) 2 CH CH 2 Ts e) (CH 3 ) 2 CH + CH 3 CH 2 CH 2 Br (CH 3 ) 2 CH-CH 2 CH 2 CH 3 + Br CH3 f) CH > Br CH3 + CH3H + Br g) Hg(Ac)2, H2 NaBH4, H > H 3.3 Br Li/ Ether Li a) b) H-C CCH3 NaBH > HCH2 CCH3 c) CH2CH2H C5H5NH + Cr3Cl > CH2C-H d) MgBr + C-H + H > > H CH

10 3.3 e) CH2Li + CH3H ---> CH3 + CH3Li f) (CH 3 ) 2 CHMgBr + CH 3 C-H ---> (CH 3 ) 2 CH 2 + CH 3 C-MgBr g) MgBr + CH3C-CH3 H > > H 3 + h) CH 3 CH 2 MgBr + H-C-H ---> > CH 3 CH 2 CH 2 H H C(CH3)2 i) CH2MgBr + C-CH3 H > > H CH2CCH2 + CH3H 4.1 Syntheses: a) b) CH 3 CH 2 H + HBr CH 3 CH 2 Br + H 2 (CH 3 ) 2 CHH + Na (CH 3 ) 2 CHNa + 1/2 H 2 CH 3 CH 2 Br + (CH 3 ) 2 CHNa CH 3 CH 2 CH(CH 3 ) 2 + NaBr c) BH3, THF H 22, H =CH > > CH2H

11 d) =CH2 4.2 More syntheses: a) C-H H2, H 2S > LiAlH4 acid > > CH3 H CH2H H 3 + b) CH 3 CH=CH 2 + H > CH 3 CHHCH 3 H 2 Cr 4 then CH 3 CHHCH > CH 3 CCH 3 c) Br Mg > ether MgBr CH3CH > acid > H CHCH 3 d) CH2H HBr > Mg > ether CH2MgBr > H3+ CH2CH2CH2H < f)

12 5. Mechanisms: a) CH=CH2 + H 2 H2S 4, heat > CH2CH3 H CH=CH2 + H 2S > CHCH 3 + HS 4 CHCH > CH2CH3 H CH2CH3 CH2CH3 + H > H2 CH2CH3 CH2CH3 + HS > H2 H + H 2S 4 H 2 S 4 b) (CH 3 ) 3 CCH 2 H > H 2 + (CH 3 ) 2 C=CHCH 3 (CH3)3CCHCH 3 + H 2S > HS4 + (CH 3)3CCHCH 3 H H 2 (CH3)3CCHCH > H2 + (CH 3)3CCHCH 3 H 2 (CH3)2C CHCH > (CH3)2C CHCH3 CH3 CH 3 (CH3)2C CH(CH3)2 + HS 4 H -----> H2S 4 + (CH 3)2C=C(CH3)2

13 c)

14 Name Second Drill Test (Sample A) rganic Chemistry 2220DR Answer All Questions 1. Draw: cis-3-isopropylcyclopentanol 2. Name: (CH 3 ) 2 CHCH 2 CH 2 CHCH 2 CH 3 CH 2 CH 2 CH 3 3. Which of the following compounds has the HIGHEST boiling point? CH2H CH3 CH3 Cl 4. Predict the product or products of each of the following reactions. 5. Propose a synthesis of each of the following compounds, beginning with the given starting material and using also any needed reagents or solvents. a) CH2CHCH 3 from CH2CH=CH2 H b) (CH3)2CHCH 2CH2CH3 from (CH3)2CHCH 2H

15 6. Propose a mechanism for the reaction shown:

16 Name Second Drill Test (Sample B) rganic Chemistry 2220DR Answer All Questions 1. Give the IUPAC name of each of the following compounds. H a) b) c) CH3 2. Which of the following compounds has the LWEST boiling point? A. (CH 3 ) 2 CHCH(CH 3 ) 2 B. CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 C. (CH 3 ) 2 CHCHHCH(CH 3 ) 2 D. CH 3 CH 2 CH 2 CH 2 CHHCH 3 3. Predict the product of each of the following reactions. 4. Propose a synthesis of each of these compounds starting from 3,3-dimethyl-1-butene and any other needed reagents. a) 3,3-dimethyl-1-butanol b) 3,3-dimethyl-2-butanol

17 5. Propose a mechanism for the following reaction:

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