Alcohols and Phenol - Belle Vernon Area School District

Alcohols and Phenol Chapter 4 Bonding Covalent bonds can be either polar or non polar Polar covalent bonds with equal sharing of e-s

Non-Polar covalent bonds with unequal sharing of e-s Non-Polar Bonds Always form nonpolar molecules Equal distribution of electrons No charged areas

Polar Bonds In symmetrical molecules nonpolar molecules Bonds are equidistant from each other if symmetric In unsymmetrical molecules polar molecules

Charged areas due to uneven edistribution Polar Bonds + - H Cl Attractive Forces in Molecules

Nonpolar molecules are held together by LDF (attractions between temporary dipoles and induced dipoles) Induced dipoles temporary dipoles formed by the attraction of one atoms nucleus for another atoms e-s

Polar Molecules are held together by either Dipole-Dipole attractions Attraction between oppositely charged poles on 2 polar molecules Hydrogen Bonds (very strong dipoledipole) The attraction between the + charges

H on one dipole and the charged highly e-neg element in the polar molecule. Strength Order of strength H-Bond>dipole-dipole>LDF Functional Groups

Both alcohols and phenol contain OH OH Hydroxyl group Alcohol General Formula = ROH Phenol General Formula = ArOH The Difference The difference between alcohols and phenol is the O

added to make the OH group Results in 3 differences The Difference 1. Alkanes = nonpolar molecules with LDF Alcohols = have polar areas and H Bonding C C C O H

- + Nonpolar Region The Difference 2. Alkanes cannot dissolve in H2O while shorter (2-5 Cs) alcohols can 3. Alcohols have higher

boiling points that their corresponding alkanes The Difference C = -162 C C-OH = 64.5 C C-C = -88.5 C C-C-OH = 78.3 C C-C-C = 0 C C-C-C-OH = 118 C The Difference

1 alcohol hydroxyl group on 1 C C-C-C-OH 2 alcohol hydroxyl group on 2 C C-C-C OH 3 alcohol hydroxyl group on 3 C C C-C-C OH

Naming Alcohols 1. Drop e from the alkane & add ol 2. # from end closest to OH & add the # in front of the mainchain 3. The OH has priority over other functional groups covered

Name the following & write the condensed formula C-C-C-OH C-OH OH C-C-C-C-C-C-C OH

OH C-C-C-C C-C-C-C-C- OH

C-C-C-C-C OH OH More Practice Condensed Name &

Cl OH C OH C-C-C-C C-C-C-C-C-C Br Br Br OH C-C-C-C-C-C-C-C-C OH

OH C-C-C-C-C C-C-C-C-C Still More Practice! Condensed Name & OH OH

C-C-C-C-C-C-C OH OH OH Cl OH Cl

C-C-C-C-C-C C-C-C-C-C-C-C C-C Preparation of Alcohols 1. 1Alcohols a.) Alkyl halide + water alcohol + hydrogen halide

RX + H2O R-OH + HX Form 1-Propanol (str & cond) Cl OH C-C-C + H2O C-C-C + HCl CH3CH2CH2Cl + H2O CH3CH2CH2OH + HCl Reaction Practice

React ethylfluoride with water (str,cond, name product) Preparation of Alcohols (still 1) b.) Alkyl + metal alcohol + metal halide hydroxide

halide RX + M+OH- ROH + MX (M Can be Li+,Na+,or K+) Practice Form Heptanol (str and Cond) (you can choose any of the 3 metals Na is most common)

C-C-C-C-C-C-C-Cl + NaOH C-C-C-C-C-C-C-OH + NaCl CH3(CH2)5CH2Cl + NaOH CH3(CH2)5CH2OH + NaCl Practice React methyl bromide with potassium hydroxide

Synthesize Synthesize to form an organic compound from the pure hydrocarbon (usually needs more than one step) Synthesis of a 1 Alcohol requires 2 steps 1. RH + Cl2 RCl + HCl 2. RCl + H2O (or NaOH) ROH + HCl Na could be Li or K

(or NaCl) Examples Synthesize methanol (str) 1. C + Cl2 CCl + HCl 2. CCl + NaOH (or H2O) COH + NaCl (or HCl) Examples

Synthesize 1-Pentanol (condensed) CH3(CH2)3CH3 + Cl2 CH3(CH2)3CH2Cl + HCl CH3(CH2)3CH2Cl + KOH (or H2O) CH3(CH2)3CH2OH + KCl (or HCl) Preparation of 2 or 3 Alcohol

1. Alkene + water 2 or 3 Alcohol Hydrate 3-ethyl-2-pentene (str,cond,name prdct) Preparation of 2 or 3 Alcohol 2. RX + H2O ROH + HX

React 3-iodoheptane with water (str, cond, name product) Preparation of 2 or 3 Alcohol 3. RX + M+OH- ROH + MX React 2-fluoropropane with

Lithium Hydroxide (str, cond, name product) Practice Form 2-hexanol 3 ways (str) Form 3-octanol 3 ways (cond) Synthesize 2 - Butanol Reactions of Alcohols

1. Halogenation (same as alkanes) R-OH + X2 R-XOH + HX Form 3-bromo-1-heptanol (3bromoheptanol) (str and cond) Br C-C-C-C-C-C-C-OH +Br2 C-C-C-C-C-C-COH Practice Form 1,2,2,3tetrafluorohexanol

(*1-hexanol) (str&cond) Form 3-iodo-3-hexanol (str&cond) Reactions of Alcohols 2. Alcohol + hydrogen halide alkyl halide + water ROH + HX RX + H2O React methanol with hydrogeniodide

(str, cond, name product) CH3-OH + HI CH3-I + H2O Practice React 2-pentanol with Hydrogen Fluoride (str, cond, name product) Reactions of Alcohols

3. Dehydration of alcohols to form alkenes Alcohol H2SO4alkene + H2O Dehydrate 2-butanol (str&cond) OH C-C-C-C H2SO4C=C-C-C + H2O Reaction Mechanism for Dehydration of Alcohols

H C-C-OH + H+ C-C-O-H+ H

C-C-O-H+ C-C+ + H2O C-C+ C=C + H+ H Indicated Protonated Alcohol Protonated alcohol an alcohol where a H+ bonds coordinately to the hydroxyl

group giving the alcohol a positive charge Reactions of Alcohols 4. Alcohol + metal alcohol salt + H ROH + M RO-M+ + H2 *M = Na+, K+, Ba+2, Ca+2, Mg+2, Al+3

Reactions of Alcohols React ethanol with Barium C-C-OH + Ba (C-C-O-1)2Ba+2 + H2 Condensed: To Name Alcohol Salts 1. Name Metal

2. Prefix for # of Cs and follow with oxide (C-C-O-1)2 Ba+2 = barium ethoxide Practice React pentanol with lithium (str, cond, name product) 2-C-C-C-C-C-OH + 2Li 2C-C-C-C-CO-1Li+ + H2

(Coefficient for H2 groups at the end) Condensed: Name: Practice React methanol with Al (str, cond, name product) Practice

Synthesize barium octoxide (cond.) Reactions of Alcohols 5. Alcohol + metal hydroxide alcohol salt + water ROH + M+1OH-1 RO-M+ + H2O React ethanol with lithium

hydroxide (str,cond, name product) C-C-OH + LiOH C-C-O-1Li+ + H2O Lithium ethoxide Practice React propanol with Mangesium hydroxide [Mg(OH)2] (balance it) React pentanol with aluminum hydroxide (balance it)

Form barium nonoxide 2 ways (condensed) Phenol General form: ArOH C6H5OH Nomenclature: Orthobromophenol or 2bromophenol (-OH = #1 position) 2,3 dibromophenol

Preparation of Phenol ArCl + H2O or NaOH ArOH + HCl or NaCl Synthesis of phenol: ArH + Cl2 FeCl3 ArCl + HCl ArCl + H2O or NaCl ArOH + HCl or NaCl

Do synthesis structurally Reactions of Phenol 1. Halogenation: ArOH + X2 FeX3 ArXOH + HX Form 2,4-diiodophenol Reactions of Phenol 2. Nitration:

ArOH + HNO3 H2SO4ArNO2OH + H2O Form 2,3,5-trinitrophenol Reactions of Phenol 3. Friedel-Crafts Alkylation: ArOH + RCl AlCl3 ArROH + HCl Form metapropylphenol

Reactions of Phenol 4. Phenol + metal phenol salt + hydrogen ArOH + M ArO-1M+ + H2 React phenol with Lithium (need 2 rxn groups to make H2) Reactions of Phenol

5. Phenol + metal hydroxide phenol salt + water ArOH + M+OH- ArO-M+ + H2O React phenol with barium hydrxide Reactions of Phenol Synthesize aluminum phenoxide (str&cond)

1. + Cl2 FeCl3 + HCl 2. + H2O or NaOH HCl or NaCl

+ Reactions of Phenol Either 3. 6 + 2Al 2 ( O-)3Al+3 +

3H2 3. 3 3H2O + Al(OH)3 ( O-)3Al+3 +

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