H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H -

H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H - C - H | H - C - H | H Here’s a structural diagram of a typical hydrocarbon It has 14 C’s and 30 H’s so the formula is C 14 H 30 since each C is surrounded by 4 bonds typically, for ease of drawing, the H’s are left out to form a carbon skeleton diagram

Find the longest continuous carbon chain. This structure is called the parent chain. C - C - C - C - C - C - C - C | C - C- C - C | C | C This parent chain has 9 C so it starts with non. If there are no double bonds it ends with ane Nonane is the name of the parent chain To name the parent chain prefixes at the beginning of the word are used. These prefixes are determined by the number of C atoms in the parent chain.

Find the longest continuous carbon chain. This structure is called the parent chain. C - C - C - C - C - C - C - C | C - C- C - C | C | C If the carbon chain is 1 C starts with meth 2 C starts with eth 3 C starts with prop 4 C starts with but 5 C starts with pent 6 C starts with hex 7 C starts with hept 8 C starts with oct 9 C starts with non 10 C starts with dec This parent chain has 9 C so it starts with non. If there are no double bonds it ends with ane Nonane is the name of the parent chain

C - C - C - C - C - C - C - C | C - C- C - C | C | C Next you must number the parent chain Chains can be numbered from either direction so the rule to follow states: Number the chain so the lowest possible number is used when the 1st side chain is encountered 12345 67 8 9 98765 4 3 2 1 Using the red numbers the 1st side chain is encountered at the 5th C Using the blue numbers the 1st side chain is encountered at the 3rd C

C - C - C - C - C - C - C - C | C - C- C - C | C | C 98765 4 3 2 1 Next, identify the side chains and where they are attached 3 C side chain is called propyl 2 C side chain is called ethyl Notice all side chains end in yl

C - C - C - C - C - C - C - C | C - C- C - C | C | C 98765 4 3 2 1 Now lets consider the names which have been determined Parent chain is nonane side chains are 3-ethyl and 5-propyl the complete name is 3-ethyl-5-propylnonane Side chains appear 1st and are always alphabetized, (ethyl before propyl), parent chain appears last

Now draw the skeleton structure for 5-butyl- 6-ethyl-2-methyl decane 1st identify the parent chain 5-butyl-6-ethyl-2-methyl decane (decane means 10 C’s with no double bonds C - C - C - C - C - C - C - C - C - C Side chains are: 2-methyl (1 C attached to the 2nd C) | C 5-butyl 4 C’s attached to the 5th C 6-ethyl 2C’s attached to the 6th C | C | C | C | C | C | C

Now draw the skeleton structure for 3,3- diethyl-2,5,6-trimethylheptane 1st identify the parent chain 3,3-diethyl -2,5,6-trimethylheptane (heptane means 7C’s with no double bonds C - C - C - C - C - C - C Side chains are: 3,3-diethyl (2C attached to each side of the 3rd C) 2,5,6-trimethyl 1C’s attached to the 2nd, 5th and 6th C | C | C | C | C | C | C

Name the following: C C - C C | | | C - C - C - C - C - C - C - C | | | | C C C C Parent Chain is octane Side Chains are 2,2,3,4,7,7 hexamethyl 6 - eth yl Final Answer is 6 - eth yl - 2,2,3,4,7,7 - hexamethyl octane

Naming Cyclic Hydrocarbons with Side Chains What is this structure called? cyclopentane CH 3 Number the carbons in the ring using the lowest possible numbers. 1 23 4 5 1,2,4-trimethyl

Draw 2,3-diethyl-1-methylcyclohexane

Aromatics with Side-Chains CH 2 CH 2 CH 3 Name? 1,3-dipropylbenzene

Sometimes compounds are more easily named when the benzene ring is considered to be a side chain. Name? 2,2,3-trimethyl-4-phenylhexane

Draw 2,3-dimethyl-2,3-diphenylpentane CCCCCCCCCC C C

Alkyl Halides-Hydrocarbons containing F, Cl, Br, I When a halogen is introduced into a hydrocarbon molecule naming proceeds as if the halogen were simply a branch. CH 3 CH 2 CHCH 2 CH 3 | Cl is named 3-chloropentane so CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 Br is named 1-bromohexane

Draw the complete structural diagram for 4-bromo-2,5-dimethylheptane H H H H H H H | | | | | | | H-C-C -- C-C - C -- C-C-H | | | | | | | H CH 3 H Br CH 3 H H (CH 3 ) 2 CHCH 2 CHBrCH(CH 3 ) 2 named C H H C H H H H C HH C H C H Br H C HH C H H C HH

C H H C H H H H C HH C H C H H C HH C H H C HH The parent chain is Hexane the rest of it is 3 - bromo 2,5 - dimethyl, so the complete name is 3-bromo-2,5-dimethylhexane

If double bonds are present, the hydrocarbon is still named as if the halogen were absent. F-CH=CH-CH 2 -CH 3 is named 1-fluoro-1-butene CH 3 -CH=CH-CH 2 I is 1-iodo-2-butene CH 2 -CH=CH-CH 2 | | Br Br is named 1,4-dibromo-2-butene The condensed structural diagram for 1-chloro-6-iodo-2,4-hexadiene is

CH 2 -CH=CH-CH=CH-CH 2 | | I Cl

Cis and Trans Isomers Molecules with double and triple bonds cannot rotate in opposite directions on each side of the double bond so when side chains, like Cl atoms for example, are attached on each side of the double bond 2 different structures are possible. cis-1,2-dichloroethene trans-1,2-dichloroethene

Name trans-2,3-dibromo-2-pentene

CH 3 CH 2 Cl

C C H H H H H

C 2 H 4 + HCl C 2 H 5 Cl Addition Reaction Hydrohalogenation of an Alkene to an alkyl halide ethenechloroethane

Markovnikov’s Rule When non-identical atoms are added 2 products are theoretically possible. Experiments show only 1 main product is formed. The H atom will bond to the C atom which already has more H’s attached. H-CH=CH-CH 3 + HBr H 2 C – CH – CH 3 or H 2 C – CH –CH 3 HBr H 2-bromopropane Main product 1-bromopropane The “rich” get “richer” 2H’s x

H Br Predict the product for the reaction below

H The H atom will bond to the C atom with the most H atoms already attached.

2-bromobutane

Draw structural diagrams showing the reaction of HF and 1-pentene HF + 2-fluoropentane

C Cl H C H Cl 2 2

C C H H H H

2 C 2 H 4 + Cl 2 C 2 H 4 Cl 2 Addition Reaction Halogenation of an Alkene to an alkyl halide ethene 1,2-dichloro ethane

C C H H H H H H

C C H H H H H

H C C H H H H

C 2 H 6 + 2Cl 2 C 2 H 4 Cl 2 +2HCl Substitution Reaction Changing an Alkane to an alkyl halide ethane 1,2 dichloro ethane

Halogens have large electronegativities so their presence on a hydrocarbon chain creates a polar region which is localized. If they are present in a balanced symmetrical pattern, the polarity is nulified and the molecule is non-polar. (C 2 Cl 6 for example). Alkyl halides have stronger intermolecular forces than their corresponding hydrocarbons due to this polarity, so they have higher MP and BP and are more soluble in polar solvents than hydrocarbons. The more halogenated the hydrocarbon, the greater the polarity and the higher the MP and BP.

are characterized by the presence of an OH group (hydroxyl). The alcohol whose parent hydrocarbon is propane can have two possible structures which are derived by replacing an H atom with an OH group. H H H | | | H - C - C - C - H | | | H H H OH Notice the OH group is either attached to the 1st or the 2nd C so the 2 possible names are 1-propanol Alcohols end in ______ol. 2-propanol OH H

Name this structure CH 3 (CH 2 ) 7 OH 1-octanolName this structure CH 3 CH 2 CH 2 CH CH 2 CH 2 CH 2 CH 3 | CH 2 CH 2 OH When a functional group like OH is present find the longest carbon chain which contains the functional group. The OH group is on the 1st carbon. 3-propyl-1-heptanol. Name this structure CH 3 CH 2 CHCH 3 | OH 2-butanol not 3 butanol is the correct name

CH 3 CH 2 CH 2 CH(OH) CH 2 CH 3 is named 3-hexanol Once the numbering system is determined by the location of the OH group, other branches, alkyl or halogen are named in the usual way CH 3 | CH 3 -CH 2 - C - OH is named | CH 3 2-methyl-2-butanol

CH 3 CH 2 CH 3 | | CH 3 C CH 2 CH 2 CCH 3 | | CH 3 CH CH 3 | OH is named Find the longest C chain which contains the OH group 2-heptanol3-ethyl-3,6,6-trimethyl- If a carbon chain has more than one OH group attached it is called a polyhydroxy compound.

Draw a structural diagram of 1,2-ethanediol. CH 2 OH | the common name for this is ethylene glycol the principal component of antifreeze. CH 2 OH | CH 3 CH 2 - C-OH | CH 2 OH Its name is 2-ethyl-1,2,3-propantriol

What is the name of the structure below: OH | CH / \ CH 2 CH 2 | | CH CH / \ / \ OH CH 2 OH 1,3,5-cyclohexanetriol

CH 3 CH=CH-CH 2 -OH is named 2-buten-1-ol CH 2 =CH-CH 2 OH is named 2-propen-1-ol the OH group takes precedence in numbering 3-buten-2-ol has the formula: H H H H | | | / H - C - C - C = C | | \ H OH H

If there is a choice of chains, the most unsaturated is chosen as long as it still contains the OH group Example - What is the name of: CH 3 - CH = C - CH 2 - OH | CH 2 CH 2 CH 3 the parent chain i s 2 - buten -1- ol The complete name is 2 - propyl -

Remembering the compounds with triple bonds are called alkynes, the structural diagram for 2-propyn-1-ol is H | H - C - C C - H | OH CH 3 -CH 2 -C-CH 2 -CH-CH 3 | | CH 3 CH 2 OH is 2,4 - dimethyl-1-hexanol

ethanol

CC H HH H

CC H HH H O H H

CC H HH H OH H

C 2 H 4 + H 2 O C 2 H 5 OH Addition Reaction Hydration of an Alkene to an alcohol ethene ethanol

The presence of the OH group makes them polar so they are soluble in water and other polar solvents and can form H bonds which is a stronger intermolecular force that dipole-dipole attractions found between polar molecules. As the non-polar hydrocarbon chain grows in the higher molecular weight alcohols the polarity decreases so the solubility diminishes but they can be used to dissolve both non-polar and polar substances. Larger molecular weight alcohols also have stronger intermolecular forces so BP increases.

Oxygen atoms can bond in the middle of a chain of carbon atoms. When this happens the compounds formed are called ethers. Example CH 3 -CH 2 -O-CH 2 -CH 2 -CH 2 -CH 3 The longest chain is used as the parent chain. This 4 carbon chain is called butane the side chain is 2 C’s + the O The side chain is called ethoxy ethoxybutane

Sketch 1,2-dimethoxycyclopentane Parent chain is cyclopentane side chains are methoxy attached to consecutive carbons in the 5 Carbon ring CH 2 / \ CH 2 CH-O-CH 3 | | CH 2 ---CH-O-CH 3

Name this structure CH 2 =CH-CH-CH 2 -CH-CH 2 -CH 3 | | CH 3 -CH 2 -O O-CH 2 -CH 2 -CH 3 parent chain is 1-heptene side chains are 3-ethoxy and 5-propoxy complete name is 3-ethoxy-5-propoxy-1-heptene

2-propanol

C C C O H H H H H H H H C C C O H H H H H H H H

C C C H H H H H H H C C C O H H H H H H H O H H

O H H 2-methylethoxypropane

2C 3 H 7 OH C 6 H 14 O +H 2 O Dehydration of Alcohols to Ethers 2-propanol 2-methylethoxy propane H 2 SO 4

The difference in En of C and O, and the V shape of the C – O – C bond make ethers slightly polar. Their MP and BP lie in between those of corresponding alcohols and hydrocarbons. They mix readily with both polar and nonpolar substances so make excellent solvents for organic reactions. The C-O bond is quite stable making ethers generally unreactive, another property of a good solvent.

Both these families have C = O groups replacing a H atom on the carbon chains. Aldehydes have this C = O group at the end of a chain, Ketones have the C = O group in the middle portion of the chain. Here are some examples of aldehydes and ketones. Decide which is which.

A.CH 3 HC=OB.CH 3 CH 2 C = O | CH 3 C. (CH 3 ) 2 CHCCH(CH 3 ) 2 || O D.HCHO aldehyde ketone E. CH 3 COCH 3 F. HCOC 2 H 5 aldehydeketone

Aldehydes end in _______________al Ketones end in _______________one ethanal is CH 3 -C=O | H propanone is CH 3 -C-CH 3 || O

Pentanone has 2 possible structures. They are CH 3 CCH 2 CH 2 CH 3 || Oand CH 3 CH 2 CCH 2 CH 3 || O 2 - pentanone 3 - pentanone

Name this structure CH 3 | O=CCHCH 2 CH 3 | CH 3 the parent chain is 3-methyl-2-pentanone

2,3-hexanedione is C - C - C - C - C - C || || O O

1,4-cyclohexanedione is CH 2 / \ CH 2 C=O | | O=C CH 2 \ / CH 2

3-penten-2-one is The functional group takes precedence over the double bond C - C - C = C - C || O

3-hydroxypentanal is C - C - C - C - C || | O OH

5-chloro-3-heptenal is C - C - C = C - C - C - C || | O Cl

Name this CH 3 C=O | CH 2 CH-CH 3 | I 4-iodo-2-pentanone

2,5-heptadien-4-one has the structural formula CH 3 CH=CH-C-CH=CHCH 3 || O

KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O 1-propanol

KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O

H H O C C O H H C H H H H

H H O C C O H H C H H H H propanal dehydration reaction

KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O 2-propanol

C C C O H H H H H H H H KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O

C C C O H H H H H H H H O

H H O C C C O H H H H H H propanone Notice when the OH group is not on the end a ketone is made

C 3 H 7 OH + O C 3 H 6 O + H 2 O 2-propanolpropanone Oxidation of Alcohols to Aldehydes or Ketones 1-propanolpropanal

The C = O bond is polar so aldehydes and ketones are soluble in water and their MP and BP lie between corresponding hydrocarbons and alcohols since the O – H bond is more polar. They also can mix with non-polar substances due to the presence of hydrocarbon chains. The longer the chains the more non- polar they are, the less soluble they are in polar solvents and the more soluble they are in non- polar solvents. Again as their molecular weights increase so do their MP and BP due to increased VdW forces.

Ethanoic Acid is CH 3 C=O | OH the name of this is CH 3 CH 2 CH=CHCOOH 2-pentenoic acid

4-hydroxy-3-iodo-2-heptenoic acid is C - C - C - C - C = C - C = O | | | OH I OH Name this CH 3 -CH-CH 2 -CH 2 -CH 3 | COOH 2-methylpentanoic acid

C C O H H C H H H H propanal KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O

C C O H H C H H H H propanal KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O `

C C O H H C H H H H Propanoic acid KMnO 4 or Cr 2 O 7 2- in H 2 SO 4 O

C 3 H 6 O + O C 2 H 5 COOH propanalpropanoic acid Oxidation of Aldehydes to Carboxylic Acids

Organic acids are polar and form H bonds so they are soluble in water. As molecular weights increase, intermolecular forces increase so BP and MP increase. As the hydrocarbon chain grows, the polarity decreases so the solubility in polar solvents decrease.

CC O H H H H H H

CC O H H H H H C C C O H H H H H H O H

CC O H H H H H C C CO H H H H H O H H

CC O H H H H H C C CO H H H H H O H H ethyl propanoate

Making Esters from Alcohols and Acids 5 C 2 H 5 OH + C 2 H 5 COOH C 2 H 5 COOC 2 H 5 + H 2 O

O = C - C - C - C - C | OH C - C - C - C - OH Alcohol is calledAcid is called 1-butanol Pentanoic acid When they combine H 2 O is removed (a dehydration synthesis) O = C - C - C - C - C | OH C - C - C - C - OH O = C - C - C - C - C | O | C - C - C - C

O = C - C - C - C - C | O | C - C - C - C When naming esters you name the alcohol 1st (remove the letters anol from the end and add the letters yl at the end. If the alcohol is 1-butanol then the name is 1-butyl. The acid name is second. If the acid is pentanoic drop the last 3 letters (oic) and add the letters oate. In this instance it becomes pentanoate. The complete name becomes 1-butyl pentanoate

O = C - C - C - C | O | C - C This ester’s name is Remember alcohol 1st Ethanol becomes ethyl Acid 2ndButanoic becomesbutanoate Ethyl butanoate Remember the double bonded oxygen atom is always joined to the acid

What is this ester’s name? O = C - C | O | C - C - C - C - C Remember alcohol 1st 2-pentanol becomes2-pentyl Acid 2ndethanoic becomesethanoate 2-pentylethanoate

Esters lack the OH group from the parent acid and alcohol so they are less polar. This means they have lower MP and BP than their corresponding acids and alcohols are less soluble in water and are not acidic. Smaller molecular weight esters have relatively weak intermolecular forces so they have strong odours.

NH 2 groups can be attached as side chains to carbon parent chains. These groups are called amines. Here is an example. 1,2-diaminopropane is CH 2 -CH-CH 3 | | NH 2 NH 2

What is the name of this structure? F-C=C-C-C-C-NH 2 | NH 2 3,5-diamino-1-fluoro-1-pentene notice the double bond takes precedence over the side chains. When a functional group is present like alcohols (OH), aldehydes (C=O), ketones, or acids, they take precedence over the double or triple bonds.

The hydrogens on the amines can be replaced by methyls (CH 3 ), ethyls (C 2 H 5 ), halides (F), etc. CH 3 -CH-CH 3 | N / \ CH 3 C 2 H 5 H When this happens the side chain is called N-ethyl-N-methyl-2-amino propane

C C H H Cl H H H N H H H

C C H H H H H N H H H

C C H H H H H N HH H

C C H H H H H N HH H aminoethane

Making Amines From Alkyl Halides CH 3 CH 2 Cl + NH 3 C 2 H 5 NH 2 + HCl

Amines are named as side chains. Name this compound Parent chain is 2-pentene 4,4-diamino-2-pentene Draw 2,2 diamino-6-methyl- 3,5-octadiene

N – H and C – H bonds are both polar and N – H bonds exhibit H bonding properties so amines are quite soluble in water. Neither bond is as polar as O – H so they have lower MP and BP than their corresponding alcohols. As molecular weight increases so does BP and MP unless no H bonding occurs. Match these MP to the diagrams 8 o C, -33 o C, 6 o C.

Remember the carboxylic acids Ethanoic Acid is CH 3 C=O | OH If the OH group is replaced by an amine the resulting functional group is called an amide. Amides are named from the parent chain NH 2 Ethanamide

3-ethyl-2-pentenamide is CH 3 -CH 2 -CH=CH-C=O | | C 2 H 5 N / \ H H

If the H’s on the NH 2 are replaced by a methyl and an ethyl CH 3 -CH 2 -CH=CH-C=O | | C 2 H 5 N / \ H CH 3 C 2 H 5 The name is N-ethyl-N-methyl-3-ethyl-2-pentenamide

Sketch the following N-ethylbutanamide CH 3 -CH 2 -CH 2 -C=O | N / \ C 2 H 5 H

CC H H H N H H HH C C C O O H H H H H H

CC H H H N H H H C C C O H H H H H H O H

H O H CC H H H N H H H C C C O H H H H H

H O H CC H H H N H H H C C C O H H H H H N-ethylpropanamide

Making Amides From Amines and Acids C 2 H 5 NH 2 + C 2 H 5 CO 2 HC 2 H 5 CONHC 2 H 5 + H 2 O

Amides are generally insoluble in water due to the relative cancellation of the 4 different polar regions (the two N – H s, the C = O and the C - N). The lower molecular weight amides are slightly soluble due to the presence of H bonding. Amides which have alkyl groups attached to the N atom have weaker intermolecular forces (due to lack of H bonding) so have lower MP and BP. The lone pair of electrons found on the N atom makes it attractive to H atoms so amines are weak bases.

NO 2 groups can be attached as side chains to carbon parent chains. These nitro groups as named as side chains much like halogens (Cl), ethers (OCH 3 ) and hydroxys (OH). Here is an example. 3-nitro-1-hexene has the structure CH 2 =CH-CH-CH 2 -CH 2 -CH 3 | NO 2

Sketch 1-methyl-2,3,4-trinitro-1,3,5- cyclohexatriene (TNT) C C C C CH 3 NO 2 H H This structure is also called trinitrotoluene (TNT). A benzene ring with a methyl group is called toluene. Benzene is also drawn like this

o o- and when functional groups are attached at adjacent locations the prefix ortho(o) is used. Here are examples of o-dichlorobenzene Cl - If functional groups are on carbons separated by one empty carbon the prefix used is meta (m) Here are examples of m -difluorobenzene. F F F F - If functional groups are on carbons separated by two empty carbons the prefix used is para (p) Here are examples of p -dibromobenzene. Br

20 different amino acids are used to assemble protein. Like the name implies amino acids have amino and carboxylic acid groups on adjacent carbons. R OH | | H-C-C=O | NH 2 Each of the 20 different amino acids has a different R group.

If the R group is methyl the amino acid is called alanine. Its structure is CH 3 OH | | H-C-C=O | NH 2 If the rules presented previously were used to name alanine it would be called 2 - aminopropanoic acid If serine is named 2-amino-3- hydroxypropanoic acid what is its structure?

H OH | | OH-CH 2 -C-C=O | NH 2 2-amino-3-hydroxypropanoic acid

Most of the dry mass of living organisms is composed of proteins. Proteins are composed of long chains of the 20 different amino acids linked end to end. Here is an example of how amino acids are chemically bonded. The product produced from 2 amino acids is called a dipeptide. Here is how dipeptides form.

H OH | | H-C-C=O | NH 2 CH 3 OH | | H-C-C=O | N / \ H H When 2 different amino acids combine the amino group of one amino acid always reacts with the carboxyl group of the other amino acid. Notice water is eliminated so this kind of reaction is called a dehydration synthesis. The product is called a dipeptide.

Remember a peptide linkage occurs between the amino group of one amino acid and the carboxyl group of another. Water is always eliminated in this dehydration synthesis. Show how a peptide bond forms from 2 amino acids if one has an R group which is a hydroxy and the other’s R group is an ethyl.

To watch a movie showing polypeptide formation click herehere

Making Aspartame - A dipeptideAspartame Phenylalanine Systematic name? 2-amino-3-phenyl-propanoic acid 180x's sweeter than sugar

Making Aspartame - A dipeptide Aspartic acid Systematic name? Aminobutandioic acid

Making Aspartame

Methyl ester of a Dipeptide methanol

Methyl ester of a Dipeptide

10% of ingested aspartame is changed into methanol which is poisonousaspartame Doseage from 1 diet drink is minimal Sucralose is probably better as an artificial sweetner. Show where this hydrolysis happens.

Methyl ester of a Dipeptide

Methanol is further oxidized into methanal, then methanoic acid. Draw these reactions. Methanoic acid can be toxic at high levels due to its inhibition of cytochrome c oxidase the last enzyme in the electron transport chain in the mitochondria. It transfers the electrons to oxygen. Complete inhibition is fatal.

sucralose Sucrose -white sugar Notice the similarites between sucralose and sucrose. Compare to aspartame

sucralose Sucrose -white sugar Aspartame

Making Acetylsalicylic Acid (ASA) AspirinAspirin Salicylic acidAcetic anhydride Ethanoyl ethanoate ASA + + Ethanoic acid Acetic acid 5% is vinegar

Let's focus on the acetic anhydride.All anhydrides are created by the elimination of water. This anhydride is formed by the reaction of 2 acetic acid molecules with the elimination of water (dehydration)

Let's focus on the acetic anhydride.All anhydrides are created by the elimination of water. This anhydride is formed by the reaction of 2 acetic acid molecules with the elimination of water (dehydration) When an anhydride is placed in water it will undergo the reverse reaction (hydrolysis). Water is added and it reforms the 2 original molecules, in this case the ethanoic acid.

Now the ethanoic acid can undergo an esterification with the alcohol group of the salicylic acid to form the ASA

ASA will sometimes smell like alcohol. This happens when the ester is hydrolyzed by water to reform the salicylic acid and ethanoic acid

Nylon is composed of gigantic molecules made up of a repeating subunit called a monomer. These extremely large molecules made up of large numbers of monomers are called polymers. Dupont, in Kingston, makes a kind of nylon called nylon 6,6. It is made from a 6 carbon dicarboxylic acid and a 6 carbon diamino compound.

1,6-diaminohexane (hexamethylene diamine) is one of these compounds and hexandioic acid (adipic acid) is the other. These molecules are combined end to end by releasing water in a dehydration synthesis. Show how this is done.

O=C-(CH 2 ) 4 -C=O | | OH OH hexandioic acid CH 2 -(CH 2 ) 4 -CH 2 | | H-N-H 1,6-diaminohexane O=C-(CH 2 ) 4 -C-N-CH 2 -(CH 2 ) 4 -CH 2 | || | | OH O H H-N-H n This n means this basic monomer is repeated over and over To watch a movie click here.here

Polymers made by the removal of water are called condensation polymers. Polyesters, like Dacron, are examples of this type of polymer. Esters are made by combining alcohols and acids. To watch a movie of polyester formation click herehere

Dacron is made from 1,2-ethanediol (ethylene glycol) and paradibenzoic acid (p- phthalic acid). Show how this polymer is made from these 2 monomers.

Addition Polymerization Alkene monomers can be combined by breaking double bonds. For movie click here.here. + + polyethylene ethene

Addition polymerization has 3 steps Initiation - a peroxide becomes a free radical( a compound with an unshared electron) When the free radical collides with a monomer it steals only 1e 1- from the double bond leaving behind another free radical. This begins the 2nd stage called elongation. The chain continues to grow until 2 free radicals collide and form a stable polymer. This stage is called the termination of the polymerization.

Show how addition polymers can be made from Propene, chloroethene, and phenylethene (styrene). These polymers are called polypropylene, polyvinyl chloride, and polystyrene.

+ + polypropylene propene H C CH 3 H n

chloroethene + + Polyvinyl chloride (PVC) H C H Cl n

Addition polymerization occurs in 3 stages: Initiation, propagation and termination. An initiating molecule like peroxide falls apart and makes a free radical with a single electron. This highly reactive particle starts the polymerization process. To go to a web site and read more click here.here

Plastics are polymers made from monomers of substituted ethene. Examples include: Teflon Plexiglass F C F n H C H COOCH 3 n Methyl-2-propenoate 1-methoxy-2-propenal tetrafluoroethene

Monomers used to make synthetic rubber isopreneneoprene Name these monomers. 2-methyl-1,3-butadiene2-chloro-1,3-butadiene The presence of the more electronegative Cl makes it more polar and less miscible with other hydrocarbons.

monomer + monomer + monomer + monomer polymer + + + Carbohydrate Polymers – starch, cellulose, glycogen The orientation of these bonds and the degree of cross-linking determines what it is.

Typical Fats (Triglycerides) glycerol Linoleic acid, (omega 6) Linolenic acid, (omega 3) Oleic acid (monounsaturate)

Soap Making Saponification + NaOH

Soap Making Saponification Na soap glycerol Na

Most soaps are made from palmitin and stearin from palm oil and olive oil. Stearic acid Palmitic acid Show, using structural diagrams, how sodium stearate is made. See pg. 134

There are 2 classes of fats which are essential in the human diet because they cannot be biosynthesized by the human body. These fats are called essential fatty acids (EFA) and as the name implies they contain the carboxyl functional group (COOH). They fall into 2 categories omega 3 and omega 6. All of these essential fatty acids are unsaturates. Essential omega 3 fatty acids include:

α-linolenic acidα-linolenic acid (ALA), eicosapentaenoic acideicosapentaenoic acid (EPA), and docosahexaenoic aciddocosahexaenoic acid (DHA). alpha-linolenic acid (18:3, ALA), eicosapentaenoic acid (20:5, EPA), and docosahexaenoic acid (22:6, DHA). These three polyunsaturates have either 3, 5 or 6 double bonds in a carbon chain of 18, 20 or 22 carbon atoms, respectively.polyunsaturates All double bonds are in the cis-configuration, i.e. the 2 H atoms are on the same side of the double bond.cis

ALA – alpha-linolenic acid (18:3) (18 carbons, 3 double bonds at positions 3,6,9 from the terminal methyl end; found in (flax seed oil) EPA – Eicosahexaenoic acid (20:5) 3,6,9,12,15 DHA - Docosohexanoic acid (22:6) 3,6,9,12,15,18 ? All three found in seaweed, cold water fish

Shortening is a semisolid fat used in food preparation, especially baked goods, and is so called because it inhibits the formation of long gluten strands in wheat-based doughs, giving them a "short" texture (as in shortbread).fatglutenwheat doughs shortbread Shortening can be made from animal fat (lard), but is more commonly a hydrogenated vegetable oil that is solid at room temperature.lard hydrogenatedvegetable oil

Shortening has a higher smoke point than butter and margarine, and it has 100% fat content, compared to 80% for butter and margarine. Crisco, a popular brand, was first produced in 1911.smoke point buttermargarineCrisco Despite its worldwide usage and availability, vegetable shortening is believed to be damaging to human health since it generally contains trans fats.trans fats Denmark banned it from foods in 2003.

Lard - rendered and clarified pork fat, the quality of which depends on the area the fat came from and the method of rendering. The very best is leaf lard, which comes from the fat around the animal's kidneys. The Nutritional Value for: lard Quantity Carbs (grams) Protein (grams) Cholesterol (milligrams) Weight (grams) Fat (grams) Saturated Fat (grams) 1 cup00195205 80.4 1 tbsp001213 5.1 Toward the late 20th century lard began to be regarded as less healthy than vegetable oils such as olive and sunflower due to its high saturated fatty acid and cholesterol content.20th centuryvegetable oilsolivesunflower

Tallow is a solid fat extracted from the tissues and fatty deposits of animals, especially from suet (the fat of cattle and sheep). Pure tallow is white, odorless and tasteless; it consists chiefly of triglycerides of stearic (CH 3 (CH 2 ) 16 COOH ), palmitic (CH 3 (CH 2 ) 14 COOH ), and oleic acids (18 carbon, monounsaturated, omega 9 fatty acid). Draw the carbon skeleton.triglycerides

A triglyceride is made by an esterification involving 1,2,3-propantriol and 3 fatty acids. Show how a triglyceride is made from oleic, stearic and palmitic acids.

Tallow is usually obtained commercially by heating suet (the hard fatty tissues around the kidneys of cattle and sheep) under pressure in closed vessels. Tallow is used to make soap and candles. It was formerly in common use as a lubricant.

The Nutritional Value for: butter DescriptionQuantity Cholesterol (milligrams) Weight (grams) Fat (grams) Saturated Fat (grams) salted1 PAT11542.5 salted1 tbsp3114117.1 salted1/2 cup2471139257.1 unsalted1 PAT11542.5 unsalted1 tbsp3114117.1 unsalted1/2 cup2471139257.1 but·ter (bŭt'ər) n. 1.A soft yellowish or whitish emulsion of butterfat, water, air, and sometimes salt, churned from milk or cream and processed for use in cooking and as a food.

canola oil (kə′nōl·ə ′öil) (food engineering) An edible vegetable oil derived from rapeseed that is low in saturated fatty acids (less than 7%), high in monosaturated fatty acids (60%), and high in polyunsaturated fatty acids (30%). Here's a comparison of some to the more common fats and oils.

The lower the saturated fat, the better

For more information click herehere

H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H -

Similar presentations

Presentation on theme: "H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H -"— Presentation transcript:

Similar presentations

About project

Feedback

Log in

Auth with social network:

H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H -

Similar presentations

Presentation on theme: "H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H -"— Presentation transcript:

Similar presentations

About project

Feedback