Download Honors Chemistry Name Julien Period _____ Date Chapter 17

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Julien
Name _________________________
Period _____ Date _______________
Chapter 17
Organic Chemistry
Organic Chemistry
10. The bonding characteristics of carbon allow the formation of many different organic molecules of
varied sizes, shapes, and chemical properties and provide the biochemical basis of life. As a basis
for understanding this concept:
a. Students know large molecules (polymers), such as proteins, nucleic acids, and starch, are formed by
repetitive combinations of simple subunits.
b. Students know the bonding characteristics of carbon that result in the formation of a large variety of
structures ranging from simple hydrocarbons to complex polymers and biological molecules.
c. Students know amino acids are the building blocks of proteins.
d.* Students know the system for naming the ten simplest linear hydrocarbons and isomers that contain
single bonds, simple hydrocarbons with double and triple bonds, and simple molecules that contain a
benzene ring.
e.* Students know how to identify the functional groups that form the basis of alcohols, ketones, ethers,
amines, esters, aldehydes, and organic acids.
f. * Students know the R-group structure of amino acids and know how they combine to form the
polypeptide backbone structure of proteins.
I. Alkanes and Naming Substituents.
Read Section 17.1 in your eText! I will write the IUPAC names and draw the condensed
structural formulas for alkanes with substituents.
Do the Introduction to Organic Molecules Tutorial!
A. The beginning of organic chemistry.
1. Organic compounds were so named because they came from an organism.
a. Organic means from an organism.
b. In 1828, German chemist, Friedrich Wöhler, did the unthinkable; he synthesized urea, an organic
protein from an inorganic compound, ammonium cyanate.
2. Organic compounds contain carbon and hydrogen, sometimes oxygen and other metallic elements.
B. Alkanes.
1. Alkanes contain carbon and hydrogen and are connected with a single bond.
2. They are named with a prefix to identify how many carbons are connected with a single bond in a
chain.
3. Chains with 1 to 4 carbons are gases at room temperature where chains of 5 to 8 carbons are liquids
at room temperature.
a. Alkanes with three or more carbons can make a variety of bent or zigzag shapes.
b. The ends of the chain will consist of a carbon with three hydrogens attached. (CH3— or —CH3)
c. The middle carbons will consist of a carbon with two hydrogens attached. (—CH2—)
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Chapter 17 Notes from Basic Chemistry
C. Naming Alkanes with substituents.
1. Branch or substituent—
2. Both of the molecules to the right have the formula, C4H10,
but have slightly different properties because of the branch.
3. Branched alkane—
4. Isomers—
Do the Naming Alkanes with Substituents Tutorial!
Do the Isomers: Diversity in Molecules Self Study Activity!
D. Rules for naming alkanes with substituents.
1. Alkyl group—
2. The alkyl group is named by replacing the ane ending of the
alkane name with yl.
3. When a halogen atom is attached to a carbon chain, it is named
as a halo group: fluoro (F), chloro (Cl), bromo (Br), or iodo (I).
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Chapter 17 Notes from Basic Chemistry
Rules for naming alkanes with substituents.
STEP 1: Write the alkane name of the longest continuous chain of carbon atoms.
STEP 2: Number the carbon atoms starting from the end near a substituent. Once you start
numbering, continue in that same direction.
STEP 3: Give the location and name of each substituent as a prefix to the alkane. Place a hyphen
between the number and the substituent name; list the substituents in alphabetical order. Use a
prefix (di, tri, tetra) to indicate a group that appears more than once. Use commas to separate
two or more numbers. When there are two or more substituents, the main chain is numbered in
the direction that gives the lowest set of numbers.
Problem 1: Give the IUPAC name for the following compound:
CH3 —
CH2 —
CH3
|
CH — CH2 —
CH3
|
CH —
CH2 —
Cl
E. Haloalkanes.
1. These derive their name from the replacement of hydrogen with a halogen.
2. Chemists often use their common names rather than their IUPAC names.
Problem 2: A haloalkane used as a fumigant has two carbon atoms and one bromine atom attached to each
carbon. What is its IUPAC name?
Br
|
H — C —
|
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Br
|
C — H
|
Page 4
Chapter 17 Notes from Basic Chemistry
H
H
Do the Drawing Haloalkanes and Branched Alkanes Tutorial!
Do the Hazardous Materials Case Study!
F. Drawing condensed structural formulas for alkanes.
1. Drawing the condensed structure, given the name, is done in reverse order.
2. First, break down each part of the name.
Problem 3: What is the structural formula for 2,4–dibromopentane.
You are now able to do Naming Alkanes with Substituents, and Problem 17.10 in
your first homework assignment.
II. Alkenes, Alkynes, and Polymers.
Read Section 17.2 in your eText! I will the IUPAC names and
formulas for alkenes and alkynes; draw the condensed structural
formulas of the monomers that form a polymer.
Do the Naming Alkenes and Alkynes Tutorial!
A. Naming alkenes and alkynes.
1. Alkenes and alkynes are unsaturated hydrocarbons because they contain double and triple bonds
respectively.
a. An alkene contains at least one double bond between carbons.
b. The simplest alkene, C2H4, is named ethene (ethylene) and has a double bond between its two
carbons.
c. An alkyne contains at least one triple bond between carbons.
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Chapter 17 Notes from Basic Chemistry
d. The simplest alkyne, C2H2, is named ethyne (acetylene) and has a triple bond between its
carbons.
Rules for naming alkanes and alkynes.
STEP 1: Name the longest carbon chain that contains the double or triple bond. Replace the
corresponding alkane ending with ene for a double bond or yne for a triple bond.
STEP 2: Number the chain starting from the end nearer the double or triple bond. The number of
the first carbon in the double bond is used to give the location of the double bond.
STEP 3: Give the location and name of each substituent (alphabetical order) with a prefix to the
alkene or alkyne name.
Do the Drawing Alkenes and Alkynes Tutorial!
Problem 4: Draw the condensed structural formula for each of the following:
a. 2–pentyne
b. 3–methyl–1–pentene
Do the Polymers Tutorial!
B. Polymers.
1. Polymers—
2. Monomers—
3. Polymers are the synthetics (plastics) that make up your clothing, furniture, car parts, plastic wrap,
and many of the everyday items upon which you depend.
C. Addition polymers.
1. Many polymers are made with addition reactions of small monomer alkenes.
2. These reactions require high temperature and pressure to add the monomers to the growing chain.
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Chapter 17 Notes from Basic Chemistry
3. The chains, up to 1000 monomers long, are very stable and unreactive so they must be recycled so
they don’t fill up landfills for extremely long periods of time.
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Chapter 17 Notes from Basic Chemistry
Problem 5: What are the name and condensed structural formula for the monomer used to prepare PVC?
You are now able to do Naming Alkenes and Alkynes and Drawing of Alkenes and Alkynes, and Problems
17.11, 17.12, 17.13, 17.14 and 17.16 in your first homework assignment.
III. Aromatic Compounds.
Read Section 17.3 in your eText! I will describe the detection and measurement of radiation.
A. Aromatic compounds.
1. Aromatic compounds are made of rings of six carbons with fragrant odors.
a. Benzene—
b. Aromatic compound—
c. August Kekulé proposed that the carbon atoms were arranged in a flat ring with alternating
single and double bonds between the carbon atoms.
d. Scientists have discovered that each of the bonds is equal so the electrons don’t have alternate
double and single bonds but share the electrons equally.
Do the Naming Aromatic Compounds Tutorial!
B. Naming aromatic compounds.
Rules for naming aromatic compounds.
STEP 1: Write the name of the aromatic
compound. Aromatic compounds that
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Toluene
Aniline
Phenol
(methylbenzene) (aminobenzene) (hydroxybenzene)
Chapter 17 Notes from Basic Chemistry
contain a benzene ring with a single substituent are usually named as benzene derivatives.
However, many of these compounds have been important for many years and still use their
common names. Names such as toluene, aniline, and phenol are allowed by IUPAC rules.
STEP 2: Number the aromatic ring starting from the substituent.
STEP 3: Give the location and name of each substituent as a prefix to the name. When there are
two or more substituents on a benzene ring, the ring is numbered to give the lowest numbers of
the substituents. The substituents are named alphabetically. A prefix (di, tri, tetra) is used to
indicate two or more of the same substituents. When a benzene ring is a substituent, C6H5—, it
is named as a phenyl group
Problem 6: Give the IUPAC name for the following compound:
You are now able to do Naming Aromatic Compounds and Problems 17.22 and 17.24 in your first homework
assignment.
IV. Alcohols, Phenols, and Ethers.
Read Section 17.4 in your eText! I will write the IUPAC and common names of alcohols,
phenols, and ethers; draw the condensed structural formulas when given their names.
Do the Nuclear Chemistry Self Study Activity!
A. Alcohols, phenols, and ethers.
1. Alcohols and ethers are two organic compounds that contain oxygen.
2. In an alcohol, a hydroxyl group (—OH) replaces a hydrogen atom in an alkane.
3. In an ether, an oxygen atom is attached to two carbon atoms.
4. Phenol—
B. Naming alcohols.
Rules for naming alcohols.
STEP 1: Name the longest carbon chain containing the —OH group. Replace the e in the alkane
name with ol.
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Chapter 17 Notes from Basic Chemistry
STEP 2: Number the chain starting at the end closer to the —OH. For simple alcohols, the common
name gives the name of the carbon chain as an alkyl group (ends with yl) followed by alcohol.
1-propanol is commonly called propyl alcohol. Alcohols with one or two carbon atoms do not
require a number for the hydroxyl group.
STEP 3: Give the location and name of each substituent relative to the —OH group.
STEP 4: An aromatic alcohol is named as a phenol. When there is a second substituent on the
benzene ring, the ring is numbered from the carbon 1, which is attached to the —OH group, to
give the lower possible number to the substituent.
Problem 7: Give the IUPAC name for the following:
CH3 — CH — CH2 — CH2 — OH
|
Cl
Do the Naming Ethers Tutorial!
Do the Drawing Ethers Tutorial!
C. Naming ethers.
1. Most ethers are named by their common names.
2. Write the name of each group attached to the oxygen atom, in alphabetical order, followed by the
word ether.
3. CH3—CH2—O—CH2—CH2—CH3 is named ethyl propyl ether.
D. Isomers of alcohols and ethers.
1. Alcohols and ethers can have the same molecular formula.
2. C2H6O can be ethanol (CH3—CH2—OH) or dimethyl ether (CH3—O—CH3).
Problem 8: Write the common names of the three isomers of C3H8O.
You are now able to do Problems 17.26 and 17.28 in your first homework assignment and 17.30 in your
second homework assignment.
V. Aldehydes and Ketones.
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Chapter 17 Notes from Basic Chemistry
Read Section 17.5 in your eText! I will write the IUPAC and common names for aldehydes
and ketones; draw the condensed structural formulas when given their names.
Do the Naming Aldehydes and Ketones Tutorial!
A. Aldehydes and ketones.
1. The carbonyl group consists of a carbon–oxygen double bond.
2. The double bond in the carbonyl group is similar to that of alkenes, except the carbonyl group has a
dipole.
3. The polarity of the carbonyl group strongly influences the physical properties of aldehydes and
ketones.
4. In an aldehyde, the carbon of the carbonyl group is bonded to at least one hydrogen atom.
5. That carbon may also be bonded to another hydrogen, and alkyl group, or an aromatic ring.
6. In a ketone, the carbon of the carbonyl group is bonded to two alkyl groups or aromatic rings.
B. Naming aldehydes.
Rules for naming aldehydes.
STEP 1: Name the longest carbon chain containing the carbonyl group by replacing the e in the
alkane name with al. No number is needed for the aldehyde group because it always appears
at the end of the chain. The first four unbranched aldehydes are often referred to by their
common names, which end in aldehyde. The roots of these common names are derived from
Latin or Greek words that indicate the source of the corresponding carboxylic acid.
STEP 2: Name and number the substituents by counting the carbonyl group as carbon 1.
Problem 9: What are the IUPAC and common names of the aldehyde with three carbon atoms?
C. Naming ketones.
1. In the common names, the alkyl groups bonded to the carbonyl group are named as substituents and
listed alphabetically followed by ketone.
2. Acetone, which is another name for propanone, has been retained by the IUPAC.
3. In the IUPAC system, the name of a ketone is obtained by replacing the e in the corresponding
alkane name with one.
Rules for naming ketones.
STEP 1: Name the longest carbon chain containing the carbonyl group by replacing the e in the
alkane name with one.
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Chapter 17 Notes from Basic Chemistry
STEP 2: Number the carbon chain starting from the end nearer the carbonyl group and indicate
its location. Place the number of the carbonyl carbon in front of the ketone name (propanone
and butanone do not require numbers).
STEP 3: Name and number any substituents on the carbon chain.
Problem 10: What is the common name of 3–hexanone?
You are now able to do Naming Aldehydes and Ketones and Problems 17.32, 17.34, and 17.36 in your second
homework assignment.
VI. Carboxylic Acids and Esters.
Read Section 17.6 in your eText! I will write the IUPAC and common names of carboxylic
acids and esters; draw the condensed structural formulas when given their names.
Do the Carboxylic Acids Self Study Activity!
Do the Naming and Drawing Carboxylic Acids Tutorial!
A. Carboxylic acids and esters.
1. Carboxyl group—
Rules for naming carboxylic acids.
STEP 1: Identify the longest carbon chain containing the carboxyl group and replace the e in the
alkane name with oic acid. The carboxylic acid of benzene is named benzoic acid.
STEP 2: Give the location and name of each substituent on the main chain by counting the
carboxyl group as carbon 1. For benzoic acid, where the carboxyl group is bonded to carbon
1, the ring is numbered in the direction that gives substituents the smallest possible numbers.
Problem 11: Draw the condensed structural formula of pentanoic acid
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Chapter 17 Notes from Basic Chemistry
B. Esters.
1. A carboxylic acid reacts with an alcohol to form an ester.
2. In the ester, the —H of the carboxylic acid is replaced by an alkyl group.
3. Aspirin is an ester as well as a carboxylic acid.
4. Fats and oils in our diets contain esters of glycerol and fatty acids, which are long-chain carboxylic
acids.
5. The aromas and flavors of many fruits including bananas, oranges and strawberries are due to esters.
Do the Writing Esterification Reactions Tutorial!
Do the Formation of Esters from Carboxylic Acids Tutorial!
Do the Naming Esters Tutorial!
C. Esterification.
1. Esterification—
2. An excess of the alcohol reactant is used to favor the formation of the ester product.
3. In this reaction, the —OH removed from the carboxylic acid and the —H removed from the alcohol
combine to form water.
O
O
||
||
H+ , heat
¾¾¾
¾¾¾
® CH 3—C—O—CH 3 + H—O—H
CH 3—C—OH + H—O—CH 3 ¬
acetic acid + methyl alcohol  methyl acetate + water
D. Naming esters.
1. The name of an ester consists of two words taken from the names of the alcohol and the acid from
which it was formed.
2. The first word indicates the alkyl part of the alcohol.
3. The second word is the carboxylate name of the carboxylic acid.
4. The IUPAC names of esters use the IUPAC names for the carbon chain of the acid, while the
common names of esters use the common names of each.
Problem 12: What carboxylic acid and alcohol are needed to form the following ester, which gives the
flavor and odor to apricots? (Hint: Separate the O and C=O of the ester group and add —H
and —OH to give the original alcohol and carboxylic acid.)
CH3—CH2— C—O—CH2—CH2—CH2—CH2—CH3
||
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Chapter 17 Notes from Basic Chemistry
O
E. Esters in plants.
1. Many of the fragrances of perfumes and flowers and the flavors of fruits are due to esters.
2. Small esters are volatile, so we can smell them, and soluble in water, so we can taste them.
Rules for naming esters.
STEP 1: Write the name of the carbon chain from the alcohol as an alkyl group.
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Chapter 17 Notes from Basic Chemistry
STEP 2: Change the ic acid of the acid name to ate.
Problem 13: Draw the condensed structural formula of ethyl heptanoate that gives the odor and flavor to
grapes.
You are now able to do Formation of Esters from Carboxylic Acids and Problems 17.38, 17.40, 17.46 and
17.48 in your second homework assignment.
VII.
Amines and Amides.
Read Section 17.7 in your eText! I will write the IUPAC and common names of amines and
amides; draw the condensed structural formulas when given their names.
Do the Name That Amine Tutorial!
Do the Drawing Amines Tutorial!
A. Naming Amines.
1. Amines are derivatives of ammonia (NH3) in which one or more hydrogen atoms are replaced with
alkyl or aromatic groups.
2. Methylamine has a methyl group replacing one hydrogen atom in ammonia and dimethylamine has
two methyl groups replacing two hydrogens, where trimethylamine there are three methyl groups
replacing the three hydrogens.
B. Aromatic amines.
1. The aromatic amines use the name aniline, which is approved by the IUPAC.
C. Amides.
1. The amides are derivatives of carboxylic acids in which a nitrogen group replaces the hydroxyl
group.
Do the Death by Chocolate Case Study!
Do the Amidation Reactions Tutorial!
D. Amidation.
1. Amidation—
2. A molecule of water is eliminated and the fragments of the carboxylic acid and amine molecules join
to form the amide, much like the formation of esters.
O
||
H
O H
|
||
|
CH3—CH 2 —C—OH + H—N—CH3 ¾heat
¾® CH3—CH 2 —C—N—CH3 + H—O—H
propanoic acid + methylamine  N–methylpropanamide + water
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Chapter 17 Notes from Basic Chemistry
Problem 14: What are the condensed structural formulas of the carboxylic acid and amine needed to
prepare the following amide?
O CH3
||
|
H—C—N—CH3
E. Naming amides.
1. In the IUPAC names and the common names, if any, amides are named by dropping the ic acid or
oic acid from the carboxylic acid names and adding the suffix amide.
Problem 15: Draw the condensed structural formula of benzamide.
You are now able to do Amidation Reactions and Problems 17.50 and 17.52 in your second
homework assignment.
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Chapter 17 Notes from Basic Chemistry
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Chapter 17 Notes from Basic Chemistry