CHE Study Guide - Ch Carboxylic Acid + Alcohol

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1 CHE 10 - Study Guide - Ch. 4-5 Chapter 4: Carbxylic Acids 1. Functinal Grup (Carbxyl grup): r R-COOH r R-CO H. Naming a. Identify lngest chain with carbxyl grup b. Use Parent name, change e t ic acid c. Name the rest f the mlecule like nrmal d. Use di t indicate tw carbxyl grups (ex ethanedic acid) Ethanic Acid Benzic Acid 3. Physical Prperties: a. Carbnyl Carbn Hydrxy grup hydrgen bnding b. Bp > alchls c. Slubility: i. < 4 C = infinitely ii. 4-8 C = slightly iii. > 8 C = insluable d. Dimers: Carbxylic acids tend t frm dimers which explains there high Bp e. Acids: Carbxylic acids are acids and lse the hydrxy H when in aqueus slutins 4. Classes f Carbxylic Acids (recgnize and name them) a. Saturated b. Unsaturated (C=C r C C) c. Armatics: Benzic Acid d. Dicarbxylic Acids e. Hydrxy Acids f. Amin Acids 5. Chemical Reactins (* indicates especially imprtant reactins) [O] [O] a. *Oxidatin: 1 Alchl Aldehyde Carbxylic Acid (p658 see page 555 fr additinal examples, and additinal reactin cnditins) [H ] b. Hydrlysis f Nitriles: R CN H Carbxylic Acid NH 4 (p659) c. Subsitituin: (-Cl, -OOCR, -OR, -NH ) i. Acid Chlrides: Carbxylic Acid SOCl Carbxylic Acid Chlride HCl (p661) ii. Acid Anhydride: SO Carbxylic Acid Carbxylic Acid Acid Anhydride H iii. *Esterficatin: H O (p66) Carbxylic Acid Alchl Ester H (p66)

2 Esters 1. Functinal Grup: r R-COO-R r RCO R. Naming: a. Identify the alchl prtin and use parent name, change ane t yl b. Identify the carbxylic acid prtin, i. Name the carbxylic acid, change ic acid t ate OR ii. Use parent name, change e t ate c. Ex Methylethanate Ethylbutanate 3. Physical Prperties: a. Carbnyl carbn Ether Oxygen b. Bp < Carbxylic Acids/Alchls (n hydrgen bnding) c. Slubility < Carbxylic Acids/Alchls d. Odrs: 1-10 carbn atms = fruity flavrs p664, Table 4.3) e. Make gd slvents fr plar and nnplar cmpunds because the mlecule has a plar and nnplar prtins. Used as slvent fr paints, varnish and laquer and fr rganic dyes. f. High mlar mass esters Waxes (cars, furniture) g. Plyesters (plymers) used in fabrics (Dacrn) 4. Chemical Reactins (* indicates especially imprtant reactins) H r Enzyme a. *Hydrlysis: Ester H O Carbxylic Acid Alchl (ppsite f Esterficatin) (p 667) H b. *Sapnificatin: Ester Base O Carbxylic Acid Salt Alchl (Reversible by adding Acid) (p667) 5. Gycerl Esters: (Picture n p668) a. Fats = slids at rm temperature (saturated fats frm animals) b. Oils = liquids at rm temperature (unsaturated r plysaturated frm plants) c. Principally frm f energy strage in the bdy d. Nrmally cis ismers but can make trans ismers which are bad fr yur health 6. Saps: Fat NaOH Saps (Salts f lng chain fatty/carbxylic acids Glycerl (p670) 3 NaOH 3 fat sdium hydrxide glycerl 3 sap

3 Chapter 5 Amides 1. Functinal Grup: r r. Naming a. Find lngest chain with amide grup. b. Use parent name, change e t amide c. Identify R grups attached t Nitrgen with an N instead f numbering like nrmal grups. d. Ex: Ethanamide N-Methylethanamide Benzamide 3. Physical Prperties: a. Slids b. NH grup is capable f hydrgen bnding and is respnsible fr the high Bp and high slubility f amides 4. Chemical Reactins: (* indicates especially imprtant reactins) a. *Frmatin: Carbxylic Acid Ammnia Ammnia Salt Amide H (p683) Carbxylic Acid 1 / /3 Amine Amine Salt Amide H b. *Acid Hydrlysis: Amide H O Acid Carbxylic Acid Ammnia Salt (p687) c. *Base Hydrlysis: Amide Base Carbxylic Acid Salt Ammnia(g) (p687)

4 Amines 1. Functinal Grup: Primary / 1 Secndary / Tertiary / 3 Quaternary Ammnium Salt. Naming a. Find lngest chain with amine grup b. Use parent name, change e t amine c. Identify R grups attached t Nitrgen with an N instead f numbering like nrmal grups. d. Diamines: Add di befre amine e. Ex: Methanamine -butanamine N-methyl-- butanamine Aniline 3. Physical Prperties a. N-H capable f hydrgen bnding. The mre H attached t N the mre hydrgen bnding that ccurs b. Plar cmpunds therefre very sluable in water when R < 6 Carbns c. Respnsible fr many bad drs (p693 bttm f page fr examples) - d. Weak bases: Amine H Ammnium In OH 4. Chemical Reactins: (* indicates especially imprtant reactins) a. *Alkylatin: Ammnia Alkyl Halide 1 Amine (p694) 1 Amine Amine Alkyl Halide Alkyl Halide 3 Amine Amine 3 Amine Alkyl Halide Quaternary ammnium salt 4 b. *Reductin: Amide LiAlH Amine (p694) /Ni Nitrile H Amine c. *Salt Frmatin: Amine Strng Acid AmmniumSalt (p696) d. *Frmatin: Acid Chlride (1 / Amine) Amide (p697) 5. Amines in everyday life (Sectin 5.8) a. Sulfa drugs Ampicillin t cmbat disease b. Vitamins: Thiamine (Vitamin B 1 ) c. Nvacaine d. Alkalids: Nictine, Methadne, Ccaine e. Amphetamines: Medicatins fr depressin, besity, narclepsy, alertness drugs f. Barbiturates: Depressants/sedatives g. Tranquilizers: Valium and Przac

5 Biling Pint Cmparisn f Similar Cmpunds Functinal Grup Name Biling Pint Plar Rank (mst t least) Structure Name Amide 1 Acid 118 Alchl CH 3 CH CH OH Ketne 56 4, 5 Aldehyde 49 4, 5 Amine 49 6 CH 3 CH CH NH Ester 3 7 Ether 11 8 CH 3 -O-CH CH 3 Alkane -4 9 CH 3 CH CH 3

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