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Drill. Draw & name 5 isomers of: C 3 H 5 OF. Test 6 is attached to the Poly website. Complete it & turn it in tomorrow. Aldehydes and Ketones. Aldehydes. Organic compounds with carbonyl groups on the end carbon. Aldehydes. O R-C H. Ketones.

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Drill

Drill

Draw & name 5 isomers of:

C3H5OF


Test 6 is attached to the poly website complete it turn it in tomorrow

Test 6 is attached to the Poly website. Complete it & turn it in tomorrow.


Aldehydes and ketones

Aldehydes and Ketones


Aldehydes

Aldehydes

  • Organic compounds with carbonyl groups on the end carbon


Drill

Aldehydes

  • O

  • R-C

  • H


Drill

Ketones

  • Organic compounds with carbonyl groups within carbon chains


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Ketones

  • O

  • C

  • R R


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Common Aldehydes


Drill

Formaldehyde

  • O

  • H-C

  • H

Methanal


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Acetaldehyde

  • O

  • CH3-C

  • H

Ethanal


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Propionaldehyde

  • O

  • CH3-CH2-C

  • H

Propanal


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Butyraldehyde

  • O

  • CH3CH2CH2C

  • H

Butanal


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Benzaldehyde

  • O

  • C

  • H

Almond Extract


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Cinnamaldehyde

O


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4-hydroxy-3-methoxy benzaldehyde

H3C-O

O

C

HO

H

Vanillin (Vanilla)


All trans retinal

all-trans-retinal

H

C=O


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all-trans-retinol

H

C-OH

H


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Draw: acetaldehyde & benzaldehyde


Drill

Common Ketones


Drill

Acetone

  • O

  • CH3-C

  • CH3

Propanone


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Methyl ethyl ketone

  • O

  • CH3CH2C

  • CH3

Butanone


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Cyclohexanone

O


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Benzophenone

O

C

Diphenylmethanone


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Muscone

O


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General Properties


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Polarity

Alcohols >

Aldehydes >

Ketones


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Solubility in Water

Alcohols >

Aldehydes >

Ketones


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Boiling Points

Alcohols >

Aldehydes >

Ketones


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Melting Points

Alcohols >

Aldehydes >

Ketones


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Oxidation State

Acids >

Aldehydes >

Alcohols >

hydrocarbons


Show all the oxidation steps in converting butane to 3 butenoic acid

Show all the oxidation steps in converting butane to 3-butenoic acid


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Energy State

Acids <

Aldehydes <

Alcohols <

hydrocarbons


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Chm PE Gradient

Methane:CH4 >

Methanol:CH3OH >

MethanalCH2O >

Methanoic A: HCOOH


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Chm PE Gradient

Reduced Compounds >

Less reduced

compounds >

Oxidized compounds


Organic hw

Organic HW

Draw & name 3

different aldehydes & 3

ketones that are isomers

of the aldehydes.


Drill

Determine MP order

CH3-CH3

CH3-CH2OH

CH3-CHO

CH3-COOH


Drill1

Drill:

Draw & name 5 isomers of:

C3H9NO


Drill

Making Aldehydes & Ketones


Making aldehydes

Making Aldehydes

  • Oxidation of primary alcohols


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Making Aldehydes

  • To oxidize alcohols, Hs must be removed from the OH & the adjacent carbon


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Making Aldehydes

  • OH

  • R-C-H

  • H

ox


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Making Aldehydes

  • OH

  • R-C-H

  • H

ox


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Making Aldehydes

  • OH O

  • R-C-H R-C

  • H H

ox


Common oxidizing agents

Common Oxidizing Agents

Cr2O7-2

MnO4-1


Examples

Examples:

K2Cr2O7

KMnO4


Drill

Making Ketones

  • Oxidation of secondary alcohols


Drill

Making Ketones

  • OH

  • R-C-R

ox

H


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Making Ketones

  • OH O

  • R-C-R R-C

  • R

ox

H


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t-Alcohol Ox

  • OH

  • R-C-R

  • R

ox


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t-Alcohol Ox

  • OH

  • R-C-R NR

ox

R


Name reactants predict name products

Name reactants & predict & name products

  • H3C-OH

K2Cr2O7

H2SO4


Formaldehyde

Formaldehyde

  • H

  • C=O

  • H

Methanal


Drill

Name reactants & predict & name products

K2Cr2O7

H2SO4

  • H2C-OH

  • H3C


Drill

Acetaldehyde

  • H

  • C=O

  • H3C

Ethanal


Drill

Name reactants & predict & name products

  • OH

  • H3C-CH-CH3

K2Cr2O7

H2SO4


Drill

Acetone

  • H3C

  • C=O

  • H3C

Propanone


Drill

Name reactants & predict & name products

OH

K2Cr2O7

H2SO4


Drill

Cyclohexanone

O


Drill

Name reactants & predict & name products

CH2OH

K2Cr2O7

H2SO4


Drill

Benzaldehyde

CHO


Drill

Name reactants & predict & name products

OH

K2Cr2O7

H2SO4


Organic hw draw reactants draw name products for the oxidation of each of

Organic HW: Draw reactants & draw & name products for the oxidation of each of:

  • 1-pentanol

  • Cyclopentanol

  • 1-methyl-1-cyclopentanol


Drill

Drill: Draw reactants & draw & name products for the oxidation of each of:

  • 1-butanol

  • 2-butanol

  • 2-methyl-2-butanol


Drill

Aldehyde Detection Reactions


Drill

Detecting Aldehydes

  • Tollen’s Test

  • Benedict’s & Fehling’s Test

  • Both distinguishaldehydes from ketones


Tollen s reagent

Tollen’s Reagent

100 %

  • AgNO3 Ag+ + NO3-

  • Ag+ + 2 NH3

  • [Ag(NH3)2]+


Drill

Tollen’s Test

  • O

  • R-C-H + 2[Ag(NH3)2]+ + 2OH-

  • O

  • NH4+R-CO- + 2Ag(s)+3NH3 + H2O


Drill

Benedict’s Reagent

100 %

  • CuSO4 Cu+2 + SO4-2

  • NaOH Na+ + OH-

100 %

Fehling’s Reagent


Drill

Benedict’s Test

  • O

  • R-C-H + 2 Cu+2 + 5 OH-

  • O

  • R-C-O- + Cu2O(s) + 3H2O


Drill

a-Hydroxy Ketones

HO O

R-C-C

H R

Yield positive results in both tests


Drill draw

Drill: Draw

a-hydroxy-propanaldehyde


Drill

Carbonyl Addition Reactions


Drill

Carbonyl Addition Rxns with water

  • O

  • C + H-OH

C

Hydrate

HO

OH


Drill

Carbonyl Addition Rxns

Chloral or

trichloroacetaldehyde

  • O

  • C + H-OH

H

Cl3C

H

CCl3

C

Chloral

Hydrate

HO

OH


Drill

Carbonyl Addition Rxns

Methanal

  • O

  • C + H-OH

H

H


Drill

Carbonyl Addition Rxns

  • O

  • C + H-OH

H

H

H

H

C

Methanediol

HO

OH


Drill

Organic HW: Draw the reactants, then predict, draw, & name the products for the addition of water to each of the following:

  • Cyclohexanone

  • Acetaldehyde

  • formaldehyde


Drill

Drill: Draw the reactants, then predict, draw, & name the products for the addition of water to each of the following:

  • acetone

  • propanaldehyde

  • cyclopropanone


Drill

Carbonyl Addition Rxns with alcohols

  • O

  • C + R-OH

C

RO

OH


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Example

  • O

  • C + OH

    H3C H


Drill

HO O

C

H3C H


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Hemiketal Formation

  • O

  • C + R3-OH

R1 R2

R1 R2

Hemiketal

C

R3-O

OH


Drill

Name reactants & draw products

  • O

  • C + CH3-OH

H3CCH3


Drill

  • O

  • C + CH3-OH

CH3 CH3

H3CCH3

Hemiketal

C

H3C-O

OH


Drill

Hemiacetal Formation

  • O

  • C + R3-OH

R1 H

R1 H

Hemiacetal

C

R3-O

OH


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Hemiacetal Formation

  • O

  • C + R3-OH

H3CH

CH3 H

Hemiacetal

C

R3-O

OH


Drill

Hemiacetal Formation

  • O

  • C + R3-OH

H3CH

CH3 H

Hemiacetal

C

R3-O

OH


Draw the reactants products when water is added to 2 butanone

Draw the reactants & products when water is added to2-butanone


Drill

Draw the reactants & products when methanol is added toacetone


Full acetals ketals

Full Acetals & Ketals

  • The second addition of an alcohol to either hemi- acetals or ketals will produce full each


Schedule

Schedule

  • Modeling lab tomorrow

  • Review Monday

  • Test Tuesday


Organic hw draw the reactants then draw name the organic products when ethanol reacts with

Organic HW: Draw the reactants, then draw & name the organic products when: ethanol reacts with:

  • Butanaldehyde

  • Butanone


Modeling lab on aldehydes ketones

Modeling Lab on Aldehydes & Ketones


Drill draw reactants then draw name the products for each of the following

Drill: Draw reactants, then draw & name the products for each of the following:

  • Addition of phenol to cyclopentanone

  • Oxidation of ethanol


Identify certain aldehydes ketones

Identify certain aldehydes & ketones:


Formaldehyde acetaldehyde benzaldehyde acetone

FormaldehydeAcetaldehydeBenzaldehydeAcetone


Draw organic reactants then draw name major organic products

Draw organic reactants, then draw & name major organic products.


Drill

1)1-propanol + KMnO4

2)2-propanol + K2Cr2O7

3)2-methyl-2-propanol

+ K2Cr2O7

4)cyclohexanone + water


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5)benzaldehyde + water

6)formaldehyde + 1-butanol

7) acetone + phenol

  • 5-hydroxypentanaldehyde

  • (addition)


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1)ethanol + KMnO4

2)2-pentanol + K2Cr2O7

3)t-butanol+ K2Cr2O7

4)acetone + water

5)formaldehyde + water

6)propanaldehyde + methanol

7) 2-butanone + phenol

8) 4-hydroxybutanaldehyde (addition)


Draw name 10 carbonyl containing isomers of

Draw & Name 10 Carbonyl Containing Isomers of:

C6H12O


Drill

Drill:Name the following:

O

OH

OH


Review for tomorrow s test

Review for Tomorrow’s Test


Name the following

Name the following:

OH

O

H


Draw the following

Draw the following:

  • 3-ethyl-6-methyl-2-phenoxy-1-sulfhydryl-octa-4,5-dione


Oxidation of each with kmno 4 or k 2 cr 2 o 7

Oxidation of each with KMnO4 or K2Cr2O7:

  • 1-butanol

  • 2-butanol

  • 2-methyl-2-propanol


Carbonyl addition rxns

Carbonyl Addition Rxns:

  • 2-butanone + water

  • Propanaldehyde + water

  • Acetone + methanol

  • Acetaldehyde + ethanol


Drill

Draw the reactants & products when 5-hydroxypentanal reacts with itself


Draw name 5 isomers of c 5 h 10 o containing carbonyls

Draw & name 5 isomers of C5H10O containing carbonyls


Drill

Draw & name 10 isomers of C4H8O


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