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Considerable overlap with AS

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Page 1: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Considerable overlap with AS

Page 2: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Intermolecular forces are? Hydrogen bonding Hydrogen bonds operate between which

atoms? O(δ-) and H(δ+) Sketch diagram on page 1 of notes

Page 3: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

End in -oic acid Other than that, pretty routine Examples: 2-chlorobutanoic acid, 4-hydroxypent-3-enoic acid 3,4-dichlorobenzenecarboxylic acid See questions on pages 2&3

Page 4: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Reaction with water produces hydroxonium ions

H3C CO

O

H+ H2O

ethanoic acid

H3C CO-

O+ H3O+

ethanoate

Page 5: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Reaction with a base produces a salt + water

Note NEVER show a bond (line) between Na+ and O-

H3C CO

O

H+ NaOH

ethanoic acid(carboxylic acid)

H3C CO-

O

+Na

sodium ethanoate(carboxylate salt)

+ H2O

Page 6: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Acid base Acid carbonate Acid metal See questions on page 4

Page 7: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

As AS module Acid + alcohol ester + water Catalyst? Conc H2SO4

H2SO4C

O

O

H OC

O

O

+ H2OH

alcohol

carboxylicacid

molecule of water lost

new carbon-oxygen bond made

ester

Key

OH=

C

O

O=

H

ESTERIFICATION

Page 8: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

C C

H

H O

OH

ethanoic acid

HC

methanol

H

H

O+ H2O

H +

CO

HC

H

H

O

methyl ethanoate

H

H2SO4C

H

H

H

carboxylic acid alcohol ester water

Page 9: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 10: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 11: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 12: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 13: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Can be carried out using acid or alkali Reagents/conds for hydrolysis; Dilute aqueous NaOH Dilute aqueous HCl

Page 14: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Acid conditions

H3C C

O

O

ethanoic acid

CH3OHH3C C

O

CH3O H

H2SO4

methyl ethanoate

HO

H

+

methanol

Page 15: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

H3C C

O-

OCH3OH3C C

O

CH3O

H+ NaOH

sodium ethanoate

+Na

+

methyl ethanoate methanol

H2SO4

H3C C

O

O

H

(carboxylate salt)

ethanoic acid

Page 16: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 17: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 18: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 19: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Esters are used as food flavourings and perfumes.

Page 20: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 21: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Deduce the structure of the products of alkaline hydrolysis of the triglyceride on the previous slide.

Soap is formed

Page 22: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 23: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Depends whether the “tail” contains one or more double bonds

Page 24: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

What do cis and trans mean? Give the displayed formula of the two forms of 1,2-dichloroethene

2,3-dichlorobut-2-ene 3-bromohex-3-ene

Page 25: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

     Try this one: (numbers indicate positions of double bonds)

Cis-9-octadecenoic acid(Oleic acid) Trans-9-octadecenoic acid(Elaidic acid)

Trans-9-octadecenoic acid(Elaidic acid)

Page 26: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Octadecanoic acid 18,0 i.e. 18 C’s, no double bonds Octade-9-enoic acid, 18,1,(9) i.e. 18 C’s, 1 double bond at C No 9, (carbon

number 9 is the first forming a double bond) Octadec-9,12-dienoic acid 18,2,(9,12) etc

Page 27: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Saturated fats Bad Unsaturated fats Good Trans fats bad

Page 28: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 29: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch
Page 30: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

A modified diesel engine can run on vegetable oil – “chip fat”

Vegetable oil and biodiesel are not the same

Page 31: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

Methyl linoleate (linoleic acid = C18)

Page 32: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch

How would you convert “chip fat” into biodiesel

Page 33: Considerable overlap with AS.  Intermolecular forces are?  Hydrogen bonding  Hydrogen bonds operate between which atoms?  O(δ-) and H(δ+)  Sketch