Chapter 5 The Integumentary System Exam Two Material Covers Chapter 5, 6, & 7.
1 Announcements & Agenda (03/09/07) Exam next Wednesday! Covers Ch 7, 8, 10-12 (not 12.6, on Exam 3)...
-
date post
20-Dec-2015 -
Category
Documents
-
view
219 -
download
0
Transcript of 1 Announcements & Agenda (03/09/07) Exam next Wednesday! Covers Ch 7, 8, 10-12 (not 12.6, on Exam 3)...
11
AnnouncementsAnnouncements & Agenda& Agenda (03/09/07)(03/09/07)
Exam next Wednesday!Exam next Wednesday! Covers Ch 7, 8, 10-12 (not 12.6, on Exam 3)Covers Ch 7, 8, 10-12 (not 12.6, on Exam 3) Practice Exam Posted!Practice Exam Posted! Review Monday @ 6:30p (Room TBA)Review Monday @ 6:30p (Room TBA) Come visit Bob!!!Come visit Bob!!!
TodayToday Quiz!Quiz! Properties & Reactions of Alcohols (12.1-12.3)Properties & Reactions of Alcohols (12.1-12.3) Ethers & Thiols (12.1-12.3)Ethers & Thiols (12.1-12.3) Aldehydes & Ketones (12.4-12.5) (?)Aldehydes & Ketones (12.4-12.5) (?)
22
One Important Example: BenzeneOne Important Example: Benzene (Know This One!) (Know This One!)
• a ring of 6 C & 6 H atoms.a ring of 6 C & 6 H atoms.• a flat ring structure drawn with three double bonds. a flat ring structure drawn with three double bonds. • represented by 2 structures because electrons are represented by 2 structures because electrons are
shared among all the C atoms.shared among all the C atoms.
Last Time: Aromatic Compounds Last Time: Aromatic Compounds “Special Conjugation”“Special Conjugation”
By the way, aromatics are called as such b/c many of By the way, aromatics are called as such b/c many of them have noticeable odors!them have noticeable odors!
33
Last Time: A color debate!Last Time: A color debate!Highly conjugated pi bonds!Highly conjugated pi bonds!
Fen+N
N N
N
H3C
CH2CH3
CH2
CH3H3C
OHOOHO
It’s the HEME in It’s the HEME in hemoglobin!!!hemoglobin!!!
Note: Highly conjugated molecules are Note: Highly conjugated molecules are typically colored!typically colored!
44
Last Time: PolymerizationLast Time: Polymerization
In polymerization, small repeating units In polymerization, small repeating units called called monomersmonomers join to form a long chain join to form a long chain polymer. polymer.
monomer unit repeats
n
55
An An alcoholalcohol contains a hydroxyl group ( contains a hydroxyl group (—OH) —OH) attached to a carbon chain.attached to a carbon chain.
• occur in many important molecules like sugars and -ol occur in many important molecules like sugars and -ol compounds (cholesterol, menthol, etc.) compounds (cholesterol, menthol, etc.)
A A phenolphenol contains a contains a hydroxyl group ( hydroxyl group (—OH) attached —OH) attached to a benzene ring.to a benzene ring.
water alcoholwater alcohol phenol phenol
Last Time: AlcoholsLast Time: Alcohols
66
Properties of AlcoholsProperties of Alcohols
• contain polar OH groups. contain polar OH groups. • form hydrogen bonds with form hydrogen bonds with
other alcohol molecules.other alcohol molecules.• Short alcohols (1-4 C Short alcohols (1-4 C
atoms) are soluble in atoms) are soluble in waterwater
• > 4 C atoms less soluble> 4 C atoms less soluble
• have much higher BPs have much higher BPs than alkanes of similar than alkanes of similar mass.mass.
77
Some Typical Alcohols (Know These)Some Typical Alcohols (Know These)
OHOH ||““rubbing alcohol”rubbing alcohol” CHCH33——CHCH——CHCH33
2-propanol (2-propanol (isopropyl alcoholisopropyl alcohol))
antifreeze antifreeze HOHO——CHCH22——CHCH22——OHOH
1,2-ethanediol (1,2-ethanediol (ethylene glycolethylene glycol)) OHOH
|| glycerolglycerol HOHO——CHCH22——CHCH——CHCH22——OHOH
1,2,3-propanetriol1,2,3-propanetriol
Could make you sickCould make you sick
Will kill youWill kill you
Part of cooking oilPart of cooking oil
88
http://www.annals.org/cgi/content/full/122/6/456http://www.annals.org/cgi/content/full/122/6/456
The Elixir Sulfanilamide disaster of 1937 The Elixir Sulfanilamide disaster of 1937
105 people died 105 people died
1938 Federal Food, Drug and Cosmetic 1938 Federal Food, Drug and Cosmetic Act, which required proof of safety before Act, which required proof of safety before the release of a new drug the release of a new drug
In the 1980s similar incident happened in In the 1980s similar incident happened in Haiti killing dozens of Haitian infantsHaiti killing dozens of Haitian infants
99
Properties of PhenolProperties of Phenol
• is soluble in water. is soluble in water.
• has a hydroxyl group that ionizes slightly has a hydroxyl group that ionizes slightly (weak acid). (weak acid).
• is corrosive and irritating to skin.is corrosive and irritating to skin.
OH O-
+ H2O + H3O+
1010
Derivatives of PhenolDerivatives of PhenolCompounds of phenol are the active ingredients in the Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.essential oils of cloves, vanilla, nutmeg, and mint.
1111
Drawing structures revisitedDrawing structures revisited
HC
HC
CH
CH
CH
HC
CH3CH2CH2CHCH3
OH
HC
HC
C
CH
CH
HC
OH
OH
OH
2-pentanol
Benzene
Phenol
Traditional drawing Abbreviated drawing
1212
Naming AlcoholsNaming Alcohols• IUPAC: Alcohols will be called somethingIUPAC: Alcohols will be called somethingolol• If other functional groups present, the -OH group will sometimes If other functional groups present, the -OH group will sometimes
be named as a “be named as a “hydroxylhydroxyl” group” group
FormulaFormula IUPAC IUPAC Common NameCommon Name
CHCH4 4 methanmethanee
CHCH33─OH ─OH methanmethanolol methyl alcohol methyl alcohol
CHCH33─CH─CH33 ethanethanee
CHCH33─CH─CH22─OH ─OH ethanethanolol ethyl alcohol ethyl alcohol
• Also know common names for propyl alcohol and those mentioned Also know common names for propyl alcohol and those mentioned
earlierearlier
1313
• determined by the number of alkyl groups attached to determined by the number of alkyl groups attached to the carbon bonded to the hydroxyl.the carbon bonded to the hydroxyl.
• primary (1°), secondary (2°), or tertiary(3).primary (1°), secondary (2°), or tertiary(3).
Primary (1º) Secondary (2º) Tertiary (3ºPrimary (1º) Secondary (2º) Tertiary (3º))1 group 1 group 2 groups 2 groups 3 groups 3 groups HH CHCH33 CHCH33
|| || | |
CHCH33——CC——OH OH CHCH33——CC——OHOH CHCH33——CC——OHOH | | || | | H H H H CHCH33
Classification of AlcoholsClassification of Alcohols
1414
Reactions of AlcoholsReactions of Alcohols
1515
Combustion of AlcoholsCombustion of Alcohols
Alcohols undergo Alcohols undergo combustioncombustion with Owith O22 to produce to produce
COCO22 and H and H22O.O.
2CH2CH33OH + 3OOH + 3O22 2CO 2CO22 + 4H + 4H22O + HeatO + Heat
1616
• Alcohols Alcohols dehydratedehydrate when heated with an acid catalystwhen heated with an acid catalyst• Lose Lose —H and —OH from —H and —OH from adjacentadjacent carbon atoms carbon atoms
HH OHOH| | ||
HH——CC——CC——H H H H++, heat , heat HH——C=CC=C——H + H + HH22OO| | || | | ||
H H H H H H H H
alcoholalcohol alkenealkene
Dehydration of AlcoholsDehydration of Alcohols
1717
Learning CheckLearning Check
Write the equations for the reaction of 2-Write the equations for the reaction of 2-propanol when it undergoespropanol when it undergoes
1. combustion.1. combustion.
2. dehydration.2. dehydration.
1818
SolutionSolution
OHOH ││CHCH33─CH─CH─CH─CH3 3
= = 2-propanol 2-propanol = C= C33HH88O O
1. combustion1. combustion
2C2C33HH88O + 9OO + 9O22 6CO6CO22 + 8H + 8H22OO
2. dehydration2. dehydration OHOH │ │ HH++
CHCH33─CH─CH─CH─CH3 3 CHCH33─CH=CH─CH=CH22 + H + H22OO
Major Product: Alkene w/ Major Product: Alkene w/ more alkyl substiuentsmore alkyl substiuents
1919
When a primary alcohol is oxidized, [O],When a primary alcohol is oxidized, [O],• one H is removed from the –OH. one H is removed from the –OH. • another H is removed from the C bonded to -OH.another H is removed from the C bonded to -OH.• an aldehyde is produced.an aldehyde is produced.
[O][O] PrimaryPrimary alcoholalcohol AldehydeAldehyde
OOHH O O || [O] [O] ||||
CHCH33——CC——HH CH CH33——CC——H + H + HH22OO ||
HH EthanolEthanol Ethanal Ethanal (ethyl alcohol)(ethyl alcohol) (acetaldehyde) (acetaldehyde)
Oxidation of Primary (1Oxidation of Primary (1) ) AlcoholsAlcohols
This is a carbonyl This is a carbonyl group…group…
2020
Oxidation of Secondary (2Oxidation of Secondary (2) Alcohols) AlcoholsWhen a secondary alcohol is oxidized, [O],When a secondary alcohol is oxidized, [O],• one H is removed from the –OH.one H is removed from the –OH.• another H is removed from the C bonded to -OH.another H is removed from the C bonded to -OH.• a ketone is produced. a ketone is produced.
[O][O] secondary alcoholsecondary alcohol ketoneketone
OOHH O O ││ [O] [O] ║║
CHCH33─C─CH─C─CH33 CH CH33─C─CH─C─CH3 3 + + HH22OO
││ HH
2-propanol (isopropyl alcohol) 2-propanol (dimethyl ketone)2-propanol (isopropyl alcohol) 2-propanol (dimethyl ketone)
ASK ME ABOUT “R”!!!ASK ME ABOUT “R”!!!
2121
Oxidation of Tertiary ( 3)Oxidation of Tertiary ( 3)AlcoholsAlcohols
Tertiary 3Tertiary 3 alcohols do not readily oxidize. alcohols do not readily oxidize. [O] [O]
Tertiary alcoholTertiary alcohol no reactionno reaction OOHH
││ [O][O]
CHCH33─C─CH─C─CH33 no productno product ││
CHCH3 3 no no HH on the C-OH to oxidize on the C-OH to oxidize
2-methyl-2-propanol2-methyl-2-propanol
2222
Oxidation of Ethanol in the BodyOxidation of Ethanol in the Body
In the body,In the body,
• enzymes in the liver oxidize ethanol.enzymes in the liver oxidize ethanol.
• aldehyde product impairs coordination.aldehyde product impairs coordination.• blood alcohol over 0.4% can be fatal. blood alcohol over 0.4% can be fatal.
O O O O ║ ║║ ║CHCH33CHCH22OH CHOH CH33CH CHCH CH33COH 2COCOH 2CO22 + H + H22OO
ethanol acetaldehyde ethanol acetaldehyde
acetic acidacetic acid
2323
• acts as a depressant.acts as a depressant.• kills or disables more kills or disables more
people than any other drug.people than any other drug.• is metabolized at a rate of is metabolized at a rate of
12-15 mg/dL per hour by a 12-15 mg/dL per hour by a social drinker.social drinker.
• is metabolized at a rate of is metabolized at a rate of 30 mg/dL per hour by an 30 mg/dL per hour by an alcoholic. alcoholic.
Ethanol CHEthanol CH33CHCH22OHOH
2424
Effect of Alcohol on the BodyEffect of Alcohol on the Body
2525
% Ethanol% Ethanol ProductProduct
50%50% Whiskey, rum, brandyWhiskey, rum, brandy
40%40% Flavoring extractsFlavoring extracts
15-25%15-25% Listerine, Nyquil, ScopeListerine, Nyquil, Scope
12%12% Wine, Dristan, CepacolWine, Dristan, Cepacol
3-9%3-9% Beer, LavorisBeer, Lavoris
Alcohol Contents in Common ProductsAlcohol Contents in Common Products
2626
EthersEthers• contains an ─O─ between two carbon groups (R-O-R’).contains an ─O─ between two carbon groups (R-O-R’).• has a common name that gives the alkyl names of the has a common name that gives the alkyl names of the
attached groups followed by attached groups followed by etherether..
CHCH33─O─CH─O─CH33 CHCH33─CH─CH22─O─CH─O─CH33
dimethyl ether ethyl methyl etherdimethyl ether ethyl methyl ether
2727
Boiling Points of EthersBoiling Points of Ethers
EthersEthers• are only modestly are only modestly
polar.polar.• have an O atom, have an O atom,
but there is no H but there is no H attached. attached.
• cannot form cannot form hydrogen bonds hydrogen bonds between between etherether molecules.molecules.
2828
Solubility of Alcohols & Ethers in WaterSolubility of Alcohols & Ethers in Water
Alcohols and ethers Alcohols and ethers • are more soluble in water than alkanes because the are more soluble in water than alkanes because the
oxygen atom can hydrogen bond with water. oxygen atom can hydrogen bond with water. • with 1-4 C atoms are soluble, but not with 5 or more with 1-4 C atoms are soluble, but not with 5 or more
C atoms. C atoms.
2929
Comparing Solubility & Boiling PointsComparing Solubility & Boiling Points
Molar Boiling SolubleMolar Boiling Soluble
Compound Mass Point (°C) in Water?Compound Mass Point (°C) in Water?
AlkaneAlkane CH CH33─CH─CH22─CH─CH3 3 4444 -42-42 No No
EtherEther CH CH33─O─CH─O─CH3 3 4646 -23-23 Yes Yes
AlcoholAlcohol CH CH33─CH─CH22─OH─OH 4646 7878 Yes Yes
3030
Ethers as AnestheticsEthers as Anesthetics
Anesthetics Anesthetics • inhibit pain signals to the brain.inhibit pain signals to the brain.
• like diethyl ether CHlike diethyl ether CH33──CHCH22──OO──CHCH22──CHCH33 were used were used for over a century, but caused nausea and were for over a century, but caused nausea and were flammable.flammable.
• developed by the 1960’s were nonflammable.developed by the 1960’s were nonflammable.
Cl F F Cl F HCl F F Cl F H
│ │ ││ │ │ │ │ ││ │ │
HH──CC──CC──OO──CC──HH HH──CC──CC──OO──CC──HH
│ │ ││ │ │ │ │ ││ │ │ F F F H F HF F F H F H
Ethane(enflurane)Ethane(enflurane) Penthrane Penthrane
3131
MTBEMTBE
Methyl Methyl terttert-butyl ether -butyl ether CHCH33
││
CHCH33──OO──CC──CHCH33
││
CHCH33
• is second in production of organic chemicals. is second in production of organic chemicals.
• is an additive used to improve gasoline performance.is an additive used to improve gasoline performance.
• use is questioned since the discovery that MTBE has use is questioned since the discovery that MTBE has contaminated water supplies.contaminated water supplies.
3232
ThiolsThiols• are carbon are carbon
compounds that compounds that contain a –SH group.contain a –SH group.
• are named in the are named in the IUPAC system by IUPAC system by adding adding thiolthiol to the to the alkane name of the alkane name of the longest carbon chain.longest carbon chain.
• the -SH group may the -SH group may also be called a also be called a ““mercaptomercapto” group” group
3333
ThiolsThiolsThiols Thiols • often have often have
strong odors.strong odors.
• are used to are used to detect gas detect gas leaks.leaks.
• are found in are found in onions, oysters, onions, oysters, and garlic.and garlic.
3434
Oxidation of ThiolsOxidation of Thiols
When thiols undergo oxidation,When thiols undergo oxidation,• an H atom is lost from each of two –SH groups.an H atom is lost from each of two –SH groups.• the product is a the product is a disulfidedisulfide..
[O][O]
CHCH33─S─SHH + + HHS─CHS─CH33 CH CH33─S─S─CH─S─S─CH3 3 + + HH22OO
3535
Aldehydes and KetonesAldehydes and Ketones
An An aldehydealdehyde contains a contains a carbonyl groupcarbonyl group (C=O), which (C=O), which is a carbon atom with a is a carbon atom with a double bond to an oxygen double bond to an oxygen atom.atom.
In a In a ketoneketone, , the carbon of the carbon of the the carbonyl groupcarbonyl group is is attached to two other carbon attached to two other carbon atoms.atoms.
3636
Naming AldehydesNaming Aldehydes
3737
Aldehydes in Flavorings Aldehydes in Flavorings Several naturally occurring aldehydes are Several naturally occurring aldehydes are used as flavorings for foods and fragrances.used as flavorings for foods and fragrances.
H
O
C
H
O
CCH=CH
Benzaldehyde (almonds)Benzaldehyde (almonds)
Cinnamaldehyde (cinnamon)Cinnamaldehyde (cinnamon)
3838
Naming KetonesNaming Ketones• as IUPAC, the -e in the alkane name is replaced with as IUPAC, the -e in the alkane name is replaced with
––oneone..
• With a common name, the alkyl groups attached to the With a common name, the alkyl groups attached to the carbonyl group are named alphabetically followedcarbonyl group are named alphabetically followed
by by ketone.ketone. OO OO
║ ║ ║ ║
CHCH33 ─C─CH ─C─CH33 CH CH33─C─CH─C─CH22─CH─CH33
propanonepropanone 2-butanone 2-butanone
(dimethyl ketone) (dimethyl ketone) (ethyl methyl ketone) (ethyl methyl ketone)
3939
Ketones in Common UseKetones in Common Use
Nail polish remover, solvent
Propanone, Dimethylketone, Acetone
Butter flavoring
4040
Classify each as 1) aldehyde or 2) ketone.Classify each as 1) aldehyde or 2) ketone. OO O O
|||| || ||A. CHA. CH33——CHCH22——CC——CHCH33 B. CHB. CH33——CC—H—H
CHCH3 3 O O
| | ||||C. CHC. CH33——CC——CHCH22——CC——HH D. D.
|| CHCH33
Learning CheckLearning Check
O
4141
Properties of Aldehydes & KetonesProperties of Aldehydes & Ketones• The polar carbonyl group provides dipole-dipole The polar carbonyl group provides dipole-dipole
interactions.interactions.
+ + -- + + --
C=O C=OC=O C=O
• Without an H on the oxygen, aldehydes and Without an H on the oxygen, aldehydes and ketones cannot form hydrogen bonds to each ketones cannot form hydrogen bonds to each other. other.
4242
Boiling PointsBoiling Points
Aldehydes and ketones haveAldehydes and ketones have
• polar carbonyl groups (C=O).polar carbonyl groups (C=O). + + --
C=O C=O • attractions between polar groups.attractions between polar groups. + + -- + + --
C=O C=OC=O C=O• higher bp’s than alkanes and ethers of similar mass. higher bp’s than alkanes and ethers of similar mass.
• lower bp’s than alcohols of similar mass. lower bp’s than alcohols of similar mass.
4343
Comparison of Boiling PointsComparison of Boiling Points
4444
Solubility in WaterSolubility in Water
The electronegative O atom of the carbonyl The electronegative O atom of the carbonyl group of aldehydes and ketones forms group of aldehydes and ketones forms hydrogen bonds with water. hydrogen bonds with water.
4545
Tollens’ TestTollens’ Test
• Tollens’ reagent,Tollens’ reagent,which contains which contains AgAg++,, oxidizes oxidizes aldehydes, but aldehydes, but not ketones.not ketones.
• AgAg+ + is reduced to is reduced to metallic Ag, metallic Ag, which appears which appears as a “mirror” in as a “mirror” in the test tube.the test tube.
4646
Benedict’s TestBenedict’s Test
• Benedict’s reagent, Benedict’s reagent, which contains Cuwhich contains Cu2+2+,,
reacts with aldehydes reacts with aldehydes that have an adjacent that have an adjacent OH group.OH group.
• An aldehyde is oxidized An aldehyde is oxidized to a carboxylic acid, to a carboxylic acid, while Cuwhile Cu2+2+ is reduced to is reduced to give red Cugive red Cu22O(s).O(s).