Ogni antibiotico è efficace in relazione a un determinato gruppo di microrganismi acquista antibiotici onlinein caso di infezioni oculari vengono scelte gocce ed unguenti.

Microsoft powerpoint - chm102chapter13a

The Rules for Boiling Points
• The boiling points of compounds depend on how strongly they stick together: The more strongly they stick together, the higher the boilingpoint (the more heat it takes to rip them apart).
• There are two main forces that hold molecules together: These require both positive hydrogens (from O-H or N-H bonds) and electron lone pairs (found mainly on O and N atoms)
-London forces (see Chapter 6, pages 169-170)
-Bigger molecules have stronger intermolecular forces, and higherboiling points, other things being equal.
-These forces are very short-range, so this also depends on how close the molecules can get together. The more branches in an alkane, the harder it is for them to get close. Branched alkanes thus have lower densities and lower boiling points (see page 257).
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Recent News
• A recent report asserts that dogs have been trained to detect
cancer by sniffing samples taken from the breaths of healthy
persons and cancer victims.

• Dogs can detect odors at the low parts per billion (ppb) level.
• It is claimed that tumor cells emit different chemicals--
alkanes and benzene derivatives--than healthy cells.

• Reference: The New York Times, January 17, 2006, p. D5.
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• It is very important that you begin to
study the material as early as possible.

• Working the practice problems and
answering the practice questions is
absolutely essential.

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Functional Groups Containing the
Carbon-Oxygen Double Bond
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13.1 The Carbonyl Group • A Carbonyl Group consists of a carbon atom
and an oxygen atom joined by a double bond.
This is by definition a carbonyl group (C=O).
» Acetone for example contains a carbonyl group.
Pronounced carbon-EEL • Carbonyl groups are strongly polarized, with a partial positive charge on carbon and partial negative charge on oxygen.
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Because oxygen is more electronegative than carbon,
it pulls the electrons in the double bond toward oxygen
creating a partial negative charge on oxygen and a partial
positive charge on the carbonyl carbon atom. Much of
the reactivity of carbonyl groups results from this
polarization.

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The polarity of the carbonyl group
contributes to its reactivity.
The carbonyl carbon is bonded to oxygen and two other atoms. The bond angles between the three components on carbon are 120o or close to it.
Carbonyl compounds are broadly divided into two groups: (1) aldehydesand ketones are in one group and (2) the second group contains carboxylic acids, esters, and amides. Copyright Houghton Mifflin Company. All rights reserved.


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Structural Characteristics and
Naming of Aldehydes
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An aldehyde is a compound that has at least one
hydrogen atom attached to the carbon atom of a
carbonyl group.

The R group in an aldehyde can be
H, alkyl, or aryl.
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Some Common Aldehydes
Formaldehyde, H(C=O)H: Toxic but useful. It kills viruses, fungi, and bacteria. It is used in disinfecting and sterilizing equipment. Acetaldehyde CH (C=O)H: Sweet smelling and narcotic. Present in ripe fruits, especially in apples. It is less toxic than formaldehyde.
Benzaldehyde Ph(C=O)H: Oil of almonds; used to make dyes, perfumes, and specific flavors. Copyright Houghton Mifflin Company. All rights reserved.
Some Common Aldehydes
Some aldehydes are present in nuts and spices.
oil of almonds cinnamaldehyde
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The simplest aldehydes are known by their common names, formaldehyde, acetaldehyde, benzaldehyde, and so on. To name aldehydes systematically in the IUPAC system, the final –e of the name of the alkane is replaced by –al.
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When a compound contains more than one type of
functional group, the suffix for only one of them can
be used as the ending of the name. The IUPAC rules
define priorities that specify which suffix should be
used:

1. Carboxylic acid
2. Aldehyde
3. Ketone
4. Alcohol
5. Amine
6. Alkene
7. alkyne

Remember that alkoxy (ether), halogen (halide), and alkyl
Groups are treated as substituents and listed in
alphabetical order.

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1. To name an aldehyde, select the longest chain which
contains the aldehyde functional group.
2. Then name the parent chain by changing the -e ending
to -al.
3. Number the parent chain starting with 1 for the aldehyde
carbon atom.
4. Determine the identity of the substituents, and add this
information to the front of the parent chain name.

Note that the aldehyde is the primary functional pentane Æ pentanal group and so this isnamed as an aldehyde and pentanal Æ 3-hydroxypentanal not as an alcohol.
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Properties and Reactions
of Aldehydes
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Properties of Aldehydes and Ketones
The polarity of the carbonyl group makes aldehydes and ketones moderately polar compounds. As a result, they have boiling points higher than alkanes and are reactive.
Aldehydes and ketones do not form hydrogen bonds to each other, however, they form hydrogen bonds with water using the lone pairs of electrons on oxygen.
Aldehydes and ketones have boiling points intermediate between alkanes and alcohols of similar size. Copyright Houghton Mifflin Company. All rights reserved.


Aldehydes and ketones are soluble in common organic solvents, and those with fewer then five carbons are also soluble in water.
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Rules for Solubility
• "Like dissolves like." This means that polar compounds dissolve
best in polar solvents (like water and alcohols) and nonpolar
compounds dissolve best in nonploar solvents (like hexane and
benzene).

• Some compounds, like alcohols, have a polar part (the -OH
group) and a nonpolar part (the hydrocarbon portion). Solubility in
water depends on which part dominates. Alcohols with a large
"organic" (hydrocarbons) portion are not very soluble in water.

• Carbonyl compounds will be soluble in water if their hydrocarbon
portion is not too large. The water can form hydrogen bonds to the
electron lone pairs on the oxygen. But if the organic portion is too
large, solubility is decreased.

• Acetone, CH -(C=O)-CH , is an excellent solvent for both polar and
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--Simple ketones are excellent solvents
because they dissolve both polar and
nonpolar compounds; acetone
(CH HC=O) is an example.
--The lower boiling aldehydes and ketones are flammable.
--The simple ketones have low toxicity, however, many simple aldehydes are toxic because they react with proteins and other biomolecules; example -formaldehyde.
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Oxidation of Aldehydes
• Primary alcohols can be oxidized to aldehydes and secondary alcohols to ketones.
• Aldehydes can be further oxidized to carboxylic acids. • Since ketones cannot be further oxidized, application with a mild oxidizing agent can be used as a test to distinguish between aldehydes and ketone.
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CH CH=O + [O] → CH COOH + H O [further oxidation to an organic acid] CH CH-CH + [O] → CH (C=O)CH + H O The ketone cannot be further oxidized.
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A positive Tollens test for aldehydes involves the formation of a silver mirror. (a) An aqueous solution of ethanal is added to a solution of silver nitrate in aqueous ammonia and stirred. (b) The solution darkens as ethanal is oxidized to ethanoic acid, and Ag+1 ion is reduced to silver. (c) The inside of the beaker becomes coated with metallic silver.
The aldehyde is oxidized and the metal is reduced.
Tollens test: Ag+ (soluble) Æ Ag metal (mirror).
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Benedict's solution, which is blue in color, turns brick red when an aldehyde reacts with it.
The aldehyde
is oxidized
and

the metal is
Benedict's test: Cu++ (blue) Æ Cu+ (brick red).
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Reduction of Aldehydes and Ketones
Reduction is the reverse of the oxidation reaction. Reduction of a carbonyl group is the addition of hydrogens across the double bond to produce an –OH group. Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols.
Reduction of the carbonyl group occurs by formation of a bond to the carbonyl carbon by a hydride, H:-, ion accompanied by bonding of a H+ ion to the carbonyl oxygen atom.
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Structural Characteristics and
Naming of Ketones
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Acetone, CH (C=O)CH ): It is one of the most widely used solvents. It can dissolve most organic compounds and is also miscible with water. Acetone is highly volatile and is also highly flammable. Ketones, like aldehydes, occur widely in Nature. Copyright Houghton Mifflin Company. All rights reserved.
Some ketones are best known by their common names which give the names of the two alkyl groups bonded to the carbonyl group followed by the word ketone. For example, ethyl methyl ketone = Ketones are named systematically (IUPAC) by replacing the final –e of the corresponding alkane name with –one. The numbering of the alkane chain begins at the end nearest to the carbonyl group. The location of the carbonyl group is indicated by placing the number of the carbonyl carbon in front of the name; e.g. 2-propanone = acetone. The above compound is … Copyright Houghton Mifflin Company. All rights reserved.
Properties and Reactions
of Ketones
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The physical properties of ketones closely parallel
the properties of aldehydes; i.e. their boiling points
are intermediate between alkanes and alcohols.

Ketones are not readily oxidized.
Ketones are readily reduced to secondary alcohols.
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Chemistry at a Glance: Reactions Involving Aldehydes and Ketones Copyright Houghton Mifflin Company. All rights reserved.
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Carboxylic Acids and Their Derivatives:
Properties and Names
Caboxylic acids have an –OH group bonded to a
carbonyl group. In their derivatives, OH is
substituted by other groups. Such as,
Esters have an –OR group bonded to a carbonyl
group.
Amides have an –NH group bonded to a carbonyl
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Carboxylic Acids
are acidic

Carboxylic acids donate a proton to bases.
Carboxylic acids hydrogen bond with each other. As a result of hydrogen bonding, they have higher boiling points than similar alkanes.
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Learn these names Copyright Houghton Mifflin Company. All rights reserved.
Two common NSAID's (non-steroidal anti-inflammatory
drugs) are Ibuprofen (a.k.a. Motrin and Advil) and
Naproxen (a.k.a. Naprosyn and Aleve). They are both
carboxylic acids.

Chronic long term used of these OTC drugs has recently
been shown to increase the risk of heart disease.

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Advil and Aleve
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--Carboxylic acids have a sharp and
strong odor.
--Up to four carbon containing
carboxylic acids are water soluble.
--Carboxylic acids are named
systematically (IUPAC) by replacing
the –e at the end of the alkane name
with – oic acid. If alkyl or other
substituents are present, the chain
is numbered beginning at the
COOH end.

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Carboxylic acids have a higher priority when naming.
Therefore, this molecule is not named as a ketone, butinstead is named as a carboxylic acid.
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‹ Dicarboxylic acids, which contain two
–COOH groups, include the biochemicals
succinic acid, HOOC-CH -CH -COOH, and

glutaric acid, HOOC-CH -CH -CH -COOH.
‹ Unsaturated acids are named
systematically in the IUPAC system
with the ending –enoic acid.
‹ Acids with larger saturated alkyl
groups are waxy, odorless solids.
‹ Water solubility decreases as the size
of the alkyl group increases.

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Chemical Portraits: Commonly Encountered Carboxylic Acids Copyright Houghton Mifflin Company. All rights reserved.
Properties and Reactions of
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Notes on Some Common Carboxylic Acids
Formic acid, HCOOH: Chemical that is present in the sting of ants.
Acetic acid, CH COOH: dilute (5%) aqueous acetic acid is known as vinegar.
Butyric acid, CH CH CH COOH: Chemical responsible for odor of rancid butter.
Amino acids, the building blocks of proteins, have the general formula R-CH(NH )-COOH.
Citric acid: Present in citrus fruits and blood.
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Acidity of Carboxylic Acids
Carboxylic acids are weak acids.
Acid strengths of common carboxylic acids are about the same as that for acetic acid.
Carboxylic acids undergo neutralization reactions with bases and produce water and a carboxylic acid salt.
The sodium and potassium salts of carboxylic acids are ionic solids that are more soluble in water than the carboxylic acids themselves.
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Carboxylic acids are acids because they donate
a proton to a base; e.g. water.

butyric acid
A carboxylate ion is a negative ion produced when a
carboxylic acid loses a proton (acidic hydrogen atom).
In this case the equilibrium lies far to the left because
carboxylic acids are weak acids and therefore do not
completely ionize.

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A given carboxylic acid molecule can form two hydrogen bonds to another carboxylic acid molecule, producing a "dimer." Dimers have twice the mass of a single molecule, and a higher temperature is needed to boil carboxylic acids than would be needed if no dimers were present.
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The boiling points of monocarboxylic acids compared to those of other types of compounds. All compounds in the comparison have unbranched carbon chains.
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The solubility of saturated unbranched-chain carboxylic acids decreases as carbon-chain length increases.
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Carboxylic acids react completely with strong bases
such as NaOH. The resulting carboxylate salts are
converted back to the carboxylic acid with strong acids.

Carboxylic acids react with alcohols to produce esters.
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Carboxylic acids react with amines to produce amides.
Amides will be discussed in more detail in sections
13.10 and 13.11.

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The simple esters are colorless,
volatile liquids with a pleasant smell.

Esters are neither acids nor bases in
aqueous solution.

An ester's name consists of two
words. The name of the alkyl group in
the ester group, -COOR, and the name
of the parent carboxylic acid with the
family name –oic replaced with –ate;
e.g. ethyl acetate: CH (C=O)OCH CH

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Properties and Reactions
of Esters
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To create an ester the OH group of a carboxylic
acid is replaced by an OR group. Esters cannot
form hydrogen bonds with each other. Therefore,
esters have lower boiling points than the
carboxylic acids from which they are derived.

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FORMING ESTERS FROM CARBOXYLIC ACIDS
The reactions of alcohols (R-OH) and amines
(R-NH2) with carboxylic acids follow the same
pattern – both replace the –OH group in the
acid with another group.
Esterification: Esterification is carried out by
warming a mixture of a carboxylic acid and an
alcohol in the presence of a catalytic amount of
a strong acid catalyst.
This is an elimination
reaction. Water is
R-C-OH + HO-R' → R-C-O-R' +H O
split out
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Aspirin and Other Over-the-Counter Carboxylic Acid Derivatives Aspirin: A member of a group of drugs known as salicylates. Aspirin is an analgesic (relieves pain), antipyretic (reduces fever), and anti-inflammatory (reduces inflammation). Salicylates are esters of salicyclic acid.
Early people knew that chewing willow bark could relieve pain. It was salicylic acid in the bark that caused the effect. But the acid was bitter and caused stomach problems. In 1897 German chemists at Bayer acetylated salicylic acid and gave the world Aspirin.
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Esterification = forward reaction (remove water) = reverse reaction = adding water to break a bond Copyright Houghton Mifflin Company. All rights reserved.
Selected Esters That Are Used as Flavoring Agents.
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• Amides may contain an –NH2 group or one or both of the hydrogens can be replaced with alkyl groups.
• Unsubstituted amides, RCONH2, can form three hydrogen bonds to other amide molecules and thus have higher melting and boiling points than the acids from which they are derived.
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• Unsubstituted amides, RCONH2, are named by replacing the –oic acid by – • Substituted amides are named by first specifying the alkyl group and then identifying the amide name. The alkyl substituents are preceded by the letter N to specify that the alkyl groups are attached to the nitrogen. Copyright Houghton Mifflin Company. All rights reserved.
Note on Naming These Compounds CH3- gives "acet-" HCOOH = formic acid CH3-COOH = Acetic acid HCOO- = formate ion CH3-COO- = acetate ion H(C=O)H = formaldehyde CH3(C=O)H = acetaldehyde H(C=O)NH2 = formamide CH3(C=O)NH2 = acetamide CH3(C=O)CH3 = acetone H(C=O)N(CH3)2 = N,N-dimethylformamideCH3(C=O)NH-CH2CH3 = N-ethylacetamide Copyright Houghton Mifflin Company. All rights reserved.
NAIL POLISH SOLVENTS CH3(C=O)CH3 = acetone CH3(C=O)-O-CH2CH3 = ethylacetate The Merck Index: "Caution: Inhalation may produce headache, fatigue, excitement, bronchial irritation, and, in large amounts, narcosis. Serious poisoning rare." Copyright Houghton Mifflin Company. All rights reserved.
Chemistry at a Glance: Summary of Structural Relationships for Hydrocarbon Derivatives: "H" versus "R" Copyright Houghton Mifflin Company. All rights reserved.
Urea is a one-carbon amide. Its formation is the human body's primary method of eliminating nitrogen "waste". The kidneys remove urea from the blood and provide a route for its excretion into the urine. When the kidneys malfunction, urea concentration builds up to toxic levels, a condition known as Note that urea is like acetone with the -CH3 groups replaced by -NH2 groups Copyright Houghton Mifflin Company. All rights reserved.
Tylenol, a.k.a. acetaminophen, is an amide.
In this case the amine component is an aniline. The IUPAC name is … N-(4-hydroxyphenyl)-acetamide.
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Properties and Reactions of
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Amide Formation: Amides are formed by heating a mixture of a carboxylic acid and an amine. (The reaction is best accomplished by treating an acid chloride with ammonia or an amine.) Copyright Houghton Mifflin Company. All rights reserved.
Acetaminophen: An amide that also contains a hydroxyl group. It is best known as Tylenol. It is an alternative to aspirin for pain relief, but unlike aspirin it is not an anti-inflammatory agent.
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Hydrolysis of Esters and Amides
Recall: Hydrolysis means the addition of water to split a bond.
Esters and amides undergo hydrolysis to give back the carboxylic acid and alcohol or amine.
Ester hydrolysis: Ester hydrolysis reactions can be catalyzed by either an acid or a base. Copyright Houghton Mifflin Company. All rights reserved.
• Acid catalyzed ester hydrolysis is simply the reverse of esterification reaction. In this reaction, an ester is treated with water in the presence of a strong acid catalyst such as sulfuric acid.
• Base catalyzed ester hydrolysis with a base such as NaOH or KOH is known as The product of a saponification reaction is a carboxylate anion rather then a free carboxylic acid.
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Amide hydrolysis: Amides are stable in water, but undergo hydrolysis when heated in the presence of a base or an acid. The products of amide hydrolysis reactions in the presence of a base or an acid are shown below.
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Errors in the Text
Question 13.25(d). The ring part of the structure shown should
be a phenyl (benzene) group., i.e., a hexagon with a circle inside.
On page 353: In the "Chemical Portrait" the structure shown is
actually acetaldehyde, not acetone. (The text is correct for
acetone.)
Acetone is CH -(C=O)-CH
Bonuses: Students who are first to point out any error in the text in the chapters we cover will receive a bonus of 2 points.
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Condensation Polymers:
Polyesters and Polyamides
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CONDENSATION POLYMERS These are formed by reacting difunctional monomers to give a polymer and a small molecule, usually water or HCl. Note: condensation is the reverse of hydrolysis.
A polyester polymer is a condensation polymer in which the monomers are joined through ester linkages.
Poly(ethylene terephthalate), a polymer = PET Copyright Houghton Mifflin Company. All rights reserved.
Polyamides and Polyesters • Polymer molecules are composed of thousands of repeating units, known as monomers. • Both polyamides and polyesters are polymers; they have many uses.
• Polyamides are formed by reaction between diamines • Nylons are polyamides. • Polyesters are formed by reaction between diacids and dialcohols.
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A polyamide is a condensation polymer in which the monomers are joined through amide linkages.
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A white strand of a nylon polymer forms between two layers of a solution containing a diacid (bottom layer) and a diamine (top layer).
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Polyurethanes are polymers related to polyesters and polyamides. The backbone of a polyurethane polymer contains aspects of both ester and amide functional Foam rubber in furniture upholstery (e.g. on airplanes), packaging materials, life preservers, elastic fibers, and many other products such as skin substitute membranes (Figure 13.13) contain polyurethane polymers.
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In the News
The U.S. Environmental Protection Agency (EPA) has recently
questioned the safety of perfluorooctanoic acid (PFOA), a
compound employed in making teflon and a variety of nonstick
Items.
PFOA may be a carcinogen (a cancer-causing agent).
What is the formula of PFOA? • "Perfluoro" means that all of the hydrogens attached to the carbons in the compound have been replaced by fluorine atoms.
• "Octanoic acid is an organic acid with 8 carbons, thus PFOA = CF -(CF ) -COOH Note that the acid hydrogen is not replaced by a fluorine.
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• Carbonyl compounds contain a carbonyl group • Carbonyl groups are strongly polarized, with a partial positive charge on carbon and partial negative charge on oxygen.
• Carbonyl compounds are broadly divided into two groups: aldehydes and ketones are in one group and the second group contains carboxylic acids, esters, and amides.
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Chapter Summary (Cont'd) Systematic or IUPAC names for aldehydes are derived by replacing –e at the end of the name of the alkane with –al.
• Ketones are named systematically by replacing the final –e of the corresponding alkane name with –one.
• Aldehydes and ketones do not form hydrogen bonds, as a result they have lower boiling points than alcohols of similar size.
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Chapter Summary (cont'd) • Aldehydes and ketones are soluble in common organic solvents, and those with fewer then five carbons are also soluble in water.
• Simple ketones are excellent solvents because they dissolve both polar and nonpolar compounds.
• Alcohols can be oxidized to aldehydes and ketones.
• Aldehydes can be further oxidized to carboxylic acids.
• Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols.
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Chapter Summary (cont'd) • Most carboxylic acids are weak acids but esters and amides are neither acids nor bases.
• Carboxylic acids, esters, and amides undergo carbonyl group substitution reactions.
• Simple acids and esters are liquids; all amides except formamide are solids.
• In esters, the -OH group in the acid is replaced by an -OR group of an alcohol.
• In amides, the -OH group in an acid is replaced by an –NH2 group of ammonia, or an NHR or –NR2 group of a primary or secondary amine.
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What you absolutely must know from Chapter 13
• You must know the general forms of the following compounds:
How to name aldehydes, ketones, carboxylic acids, and esters.
• The common names of certain simple compounds: formaldehyde,
acetone, formic acid, benzaldehyde, urea, formamide, acetamide,
Some important reactions:
--Primary alcohols can be oxidized to form aldehydes.
--Secondary alcohols can be oxidized to form ketones.
--Aldehydes can be further oxidized to form carboxylic acids.
--Ketones resist oxidation
--Esters can be hydrolyzed to form an alcohol and a carboxylic acid
--Amides can be hydrolyzed to form an amine and a carboxylic acid
(Hydrolysis = adding water to split up a compound)
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Chapter 13 (continued)
Polymers are large compound formed by linking smaller units called
monomers.
Condensation polymers are formed by reacting difunctional
monomers and splitting out small molecules (e.g., H O):
--A polyester is formed by the reaction of a diacid and a dialcohol:
HOOC-R-COOH + HO-R'-OH → HOOC-R-CO-O-R'-OH + H O --A polyamide (such as nylon) can be formed from the reaction of a
diacid and a diamine:
HOOC-R-COOH + HHN-R'-NH → HOOC-R-CO-NH-R'-OH + H O Copyright Houghton Mifflin Company. All rights reserved.
To Do List
Read chapter 13!!
Do additional problems
Do practice test T/F
Do practice test MC
Review Lecture notes for
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Source: http://www.chm.wright.edu/seybold/CHM102Lectures/CHM102chapter13A.pdf

Doi:10.1016/s0140-6736(11)61873-4

Adjuvant capecitabine and oxaliplatin for gastric cancer after D2 gastrectomy (CLASSIC): a phase 3 open-label, randomised controlled trial Yung-Jue Bang*, Young-Woo Kim, Han-Kwang Yang, Hyun Cheol Chung, Young-Kyu Park, Kyung Hee Lee, Keun-Wook Lee, Yong Ho Kim, Sang-Ik Noh, Jae Yong Cho, Young Jae Mok, Yeul Hong Kim, Jiafu Ji, Ta-Sen Yeh, Peter Button, Florin Sirzén, Sung Hoon Noh*, for the CLASSIC trial investigators†

Dynamic energy-aware capacity provisioning for cloud computing environments

Dynamic Energy-Aware Capacity Provisioning for Cloud Mohamed Faten Zhani University of Waterloo University of Waterloo National University of Defense Waterloo, ON, Canada Waterloo, ON, Canada Changsha, Hunan, China Joseph L. Hellerstein University of Illinois at University of Waterloo Google, Inc. Urbana-Champaign, USA Waterloo, ON, Canada Seattle, Washington, USA