NAME ________________________________ UNIT 3: ORGANIC CHEMISTRY Diagnostic Activity:
PRE-EXISTING IDEAS ABOUT RECOGNIZING AN ORGANIC COMPOUND:
1) _________________________________________________
2) _________________________________________________
ORGANIC COMPOUNDS VS. INORGANIC SUBSTANCES
These ARE ORGANIC
COMPOUNDS
These ARE NOT Organic
Compounds
*CH4(g)
*(CO3) 2-
*C8H17OH(l)
*NaHCO3(s)
*C4H10(g)
*H2O(g)
*C3H7NH2(l)
*Li2CO3(s)
*C25H52(s)
*C(s)
*CH3CH2CH2SH(g)
*NaF(aq)
* C6H12O6(s)
* C6H12O6(aq)
*CCl4(l)
*HCN(g)
*CH2CH2(g)
*O2(g)
NEW IDEAS ABOUT RECOGNIZING AN ORGANIC COMPOUND:
1) _________________________________________________
2) _________________________________________________
198
NAME __________________________________ NOTES: UNIT 3: INTRO TO ORGANIC COMPOUND
Keep This Clear
This unit is all about honing your analytical skills. Be willing to risk a little bit.
Molecules are made of atoms, bonded to each other via covalent bonds (not ionic bonds).
The chemical reactions of molecules are affected by
the structure (shape) of the molecule
the composition of the molecule (Very often, the inclusion of H, N, O and even F
affect reactions and interactions.
the pH (acidity / alkalinity) of a system.
***********************************************
I) Compounds can be classified as being INORGANIC or ORGANIC.
A) An organic compound may be generally recognized as: * a compound in which there are C to C
covalent bonds OR the presence of C to H covalent bonds ….with a number of exceptions …
This recognition skill for organic substances is poor, at best. Common definitions do not really
give us (at this point), much insight. A relatively good definition is:
An organic compound is any compound with a relatively non-reactive backbone of carbon atoms,
acting as the central atom(s), which is (are) primarily bonded via sp3 hybridized covalent bonds to
each other and bonded to hydrogen, recognized functional groups, and other chemical species (e.g.
O, N, Fe, Mg…)
http://www.iupac.org/publications/pac/1994/pdf/6605x1077.pdf
CAN I GET A GREAT BIG ......"HUH ??? What the ....?"
At this point of the course, it is difficult to understand, what that means. Heck, it can be difficult to
grasp later on! But, it is important that we get an introduction to organic chemistry. The biggest
problem rests in blending definitions for common biomolecules (those found in living organisms) and
those organic compounds, not natural to a living system (e.g. aspartame, polyethylene tetraphthalte,
etc)
1) Organic chemistry studies the synthesis and reactions of organic compounds - but there is no
official definition of "organic compounds"!!!! Historical usage, common usage and
practicality have hampered a definition. So, I will work off of a recognition skill, and
not a definition ... Why? Well, it really is a...
Chemical Issue:
(say it with an echo...)
We will use the recognition skill of C-H covalent bonds and/or C-C covalent bonds to help categorize any solid,
liquid, or gas, as an organic compound. In biology, you probably learned this recognition skill - so this chemistry
course is trying to be consistent with your past learning. However, the recognition skill is NOT a definition and it
has its flaws, if you were to try to use it as a definition.
No single definition incorporates all examples of organic compounds, at our level, and there are very few
"absolutes" about the topic. Hopefully, this passage helps you grasp why I choose to use the recognition skill and not
try to organize a single definition, for this course.
But first, let's get the basics out of the way... Organic compounds need to be ❶compounds and the atoms will be
199
bonded to each other with ❷covalent bonds, primarily.
❶ The term, Organic, is all about compounds:
One more time, “ORGANICS are compounds, not elements. So this eliminates, any matter composed solely of
elemental solid carbon. Thus, the allotropes of carbon, such as diamonds, nanotubes, and graphite [found as pencil lead,
golf club shafts etc...], are NOT organic compounds, because they are elements, NOT compounds! It is that simple.
Alloys, containing carbon (like stainless steel) are technically mixtures of metals, and a small amount of nonmetals,
thus, they are not compounds. Alloys often have a preponderance of metallic bonding (so alloys are not organic
compounds, for at least two different reasons.)
❷The term, Organic, is about bond type:
Compounds containing the polyatomic ions of; cyanide (CN-1), carbonate (CO3-2), bicarbonate (HCO3-1), are not
considered to be organic compounds. These compounds are excluded, because the most important bonding that
creates the compound in not covalent. The bonding that characterizes the compound is often predominately ionic.
So, Okay… compounds like NaCN and CaCO3 are not organic compounds.
❸ Organic is about historical use (and maybe that quantum hybridization thing)
Carbide compounds (e.g. SiC), and the oxides of carbon (e.g. CO2 and CO) are compounds and have covalent bonds,
BUT they are NOT considered to be organic compounds, (generally, for historical reasons).
So far ... So Good! This C-H and/or C-C recognition skill may just work! But there are problems… Some big
problems… So, Read on Macduff!
❹ A Few Problems
Now, undeniably, by most accounts, chemists agree that methane molecules, CH4(g) are organic.
But, methane's derivative, carbon tetrachloride, CCl4(l) is also considered to be an organic substance. But,
carbon tetrachloride, does NOT have C-C bonds nor even C-H covalent bonds!!!
Crud-Buckets!... "Houston, we have a problem"
Additionally, urea (the first compound labeled as “organic” [(NH2)2CO]) and both
oxalic acid [H2C2O4] are considered organic compounds. But, neither compound
has C-H bonds and, like methane, urea, lacks C-C bonds (sigh!).
O O
║ ║
H-O—C — C—O-H
oxalic acid
Then there are the molecules, ketomalonic acid, (HO-(C=O)3-OH) and mellitic acid (C12H6O12 ). They
both lack C-H bonds. However, no less of an authority than NASA considers them organic compounds. And not
just any compounds ... but NASA thinks that each are organic compounds that exist in extraterrestrial soils (like in
the soils of asteroids or of Mars ... linking life to outer space), and are markers of life!
So there are issues with a simple definitions...using composition as well as bonding.
Now maybe you will appreciate why I tell you that for our course, most organic compounds will have C-C bonds or
C-H bonds represented in their structure(s), with the understanding that there are exceptions to this very
generalized recognition skill.
Also, you probably know, organics are often made from atoms of both C, H, (especially the bio-organics of living organisms)
and often, species of O, N, S, Cl, Fe, Mg, Ca, F, just to mention a few.
Can I go home now and, who is this Macduff character? … So, go read a little Shakespeare.
200
B) Every carbon atom in an organic molecule will have * 4 covalent
bonds.
1) We can symbolize organic compounds with molecular, condensed, and structural
formulae
Study the diagram. The carbon atoms really form a jagged backbone, each carbon bonded to
another and then to hydrogen atoms to complete the need for 4 covalent bonds.
H H H
H H H
eg)
Molecular Formula = C3H8
| | |
| | |
HCCC H
HCCCH
| |
|
| | |
H H H
H H H
Condensed Formula = CH3CH2CH3
Study the diagram. Every C atom has * 4
represents
* 1 pair
eg) H H H H O
| | |
| //
HCCCCCOH
| | | |
H H H H
covalent bonds. Recall: each solid dash ()
of shared e-.
Molecular Formula =
Condensed Formula=
How many covalent bonds does the molecule represented above, have? *
17
eg) Study the diagram. The bonds between carbon atoms can be single bonds,
* double bonds (2 pair of shared e-) or even *
H H H
| | |
HCC = CH
|
H
triple
bonds
Molecular Formula =
Condensed Formula =
eg) Consider the structures:
which are often
written as:
or
At every vertex you assume an atom of C and of H, unless, otherwise noted.
201
TRY THIS: Complete the table for practice on interpreting formulae
Structural Formula
Condensed Formula
Molecular Formula
As a rule, hydrocarbon portions are grouped
together, and functional groups are listed
separately.
H H H H
| | | |
HCCCCH
| | | |
H H H H
*CH3CH2CH2CH3
or
* C4H10
*CH3(CH2)2CH3
H H H
| | |
H CCC OH
|
| |
H H H
*CH3CH2CH2OH
*C3H7OH
H H H
| | |
H CCC NH
|
| |
|
H H H H
*CH3CH2CH2NH2
*C3H7NH2
*CH3CHCHCH3
*C4H8
H H H H
| | | |
HCC = CCH
|
|
H
H
COOH
C6H6COOH
* C7H7O2
202
B) 2) Some chemical compounds based upon the molecule benzene (C6H6)
Trinitrotoluene
Benzoyl Peroxide
Salicylic acid
Acetaminophen
Acetylsalicylic acid
Naproxen Sodium
Ibuprofen
TNT
http://hyperphysics.phy-astr.gsu.edu/hbase/organic/aromatic2.html
BP
http://www.uspbpep.com/usp28/v28230/usp28nf23s0_m8310.htm
Napthalene
http://www.eoearth.org/article/Health_effects_of_Naphthalene/1-methylnaphthalene/2-methylnaphthalene
Salicylic acid http://en.wikipedia.org/wiki/File:Salicylic_acid_methyl_ester_chemical_structure.png
Acetaminophen http://www.chemsynthesis.com/base/chemical-structure-18651.html
Acetylsalicylic http://chrom.tutms.tut.ac.jp/JINNO/DRUGDATA/07acetylsalicylic_acid.html
Ibuprofen
Gray et al. Braving the Elements. Sausalito : University Science Books. 1995
Naproxen:
Gray et al. Braving the Elements. Sausalito : University Science Books. 1995
Folic acid
http://www.guidechem.com/cas-757/75708-92-8.html
203
Folic Acid: The B vitamin (B9) folic acid helps prevent birth defects. When
BOTH a man and woman have enough folic acid in their diet before pregnancy
(and the women while she is pregnant), a baby is less likely to have a major birth
defect of the brain or spine.
Most women do not know how important folic acid is for their bodies and for
the health of a baby, they might have in the future. They also do not know that
a woman needs to take folic acid every day, starting before she is pregnant, for
it to work to prevent birth defects. Recent reports suggest that this is true
for men as well.
Birth defects of a baby’s brain or spine happen in the first few weeks of
pregnancy, often before a woman knows that she is pregnant. That is why
it is important for a woman to get enough folic acid each day, starting before
she is pregnant.
A woman’s body uses folic acid to make healthy new cells for her baby.
Scientists are not sure how folic acid works to prevent birth defects, but they
do know that it is needed for making the cells that will form a baby’s brain,
spine, organs, skin, and bones.
Every woman needs folic acid for the healthy new cells her body makes every
day . . . even if she were not planning to get pregnant. Recent studies suggest
that folic acid is also necessary for healthy sperm. Hence, men need it as well.
(http://www.cdc.gov/ncbddd/folicacid/basics.htm)
http://womenshealth.gov/faq/easyread/folic-etr.htm
NSAID Drugs: Non-Steroidal Anti-Inflammatory Drug
Acetylsalicylic Acid
Acetaminophen
(Bayer Aspirin)
(Tylenol)
(*not technically an NSAID)
(*a slightly mis-leading title)
Ibuprofen
(Advil, Motrin)
Naproxen Sodium’s (Aleve)
activity is closely related
Anti-pyretic
(fever reduction)
* Very Good
* Good
* Very Good
Anti-inflammatory
(anti-swelling)
* Very Good
* None
* Superior
Analgesic
(pain reduction)
* Very Good
* Good to Very Good
* Very Good
204
C) Saturated Organic Molecule versus UNsaturated Organic Molecule
A)
the term
"organic
molecule"
may apply to
hydrocarbons
and their
derivatives
* Saturated
: A broad descriptive term, which tells you that every
Carbon to Carbon bond is * a single covalent bond
a) if a * double
bond or a * triple
bond exist between any pair of carbon
atoms anywhere in the molecule, that molecule is considered to be * unsaturated.
H H H H H
| | | | |
HCCCCCH
| | | | |
H H H H H
This is an example of a C-C single bond
H H
H H O
| |
| | //
HCCOCCCOH
| |
| |
H H
H H
H H H
| | |
HCC = CH
|
H
The bonds between C atoms are * single
Even though there is the double bond between C and O
this molecule is still classified as * saturated.
Note the double bond between two of the carbon atoms
This molecule is considered to be * an UNsaturated molecule
Question: Which of one of these two structural formulae represents a saturated molecule?
H
H H H O
|
| | | //
a)
HC=CCH
b)
HCCCCH
| | |
| | |
H H H
H H H
2) Relevance to us: Saturated fats tend to lead to the development of cholesterol. Saturated fats
tend to solidify in the refrigerator or even at room temperature.
205
Relevance: Cholesterol continued....
Cholesterol is not water-soluble (nonpolar) and it must bind
to special proteins (apoproteins) before it can be carried in the
bloodstream. Once coated, they form a package called
a lipoprotein
There are 2 common categories of lipoproteins:
Low-density lipoprotein (LDL), often (& somewhat incorrectly) referred to as “bad cholesterol”
LDL is the major cholesterol carrier in the blood. When the concentration of LDL in the blood is
too high, it can precipitate out as a hard, jagged plaque and build up on artery walls. A high level
of LDL cholesterol may give you an increased risk of coronary heart disease. However, this is
the cholesterol converted into other chemicals such as testosterone and progesterone, and these
are necessary hormones for reproduction. Too much, is “bad”, because the excess gets stored.
High-density lipoprotein (HDL), commonly known, as good cholesterol: HDL is actually good
for maintaining the health of the heart and preventing the narrowing of the arteries
(atherosclerosis) because it appears to carry LDL cholesterol away from the arteries and back to
the liver for disposal.
This is why the ratio between LDL and HDL cholesterol is important. Usually the body
maintains a balance of cholesterol, making more when it needs it and getting rid of any excess.
But sometimes this balance goes wrong. LDL levels can be lowered by eating a low fat diet, rich
in soluble fiber and the HDL levels can be raised by exercising. http://www.homehealth-uk.com/index.html?f=body|fr=http://www.homehealthuk.com/medical/cholesterol.htm|r
For information re: types of fat / good stuff about fat and bad stuff: http://lpi.oregonstate.edu/ss08/fat.html
http://www.webmd.com/heart-disease/atherosclerosis-19012
http://www.nature.com/nm/journal/v17/n11/fig_tab/nm.2515_F2.html
206
Because so many of us have parents or grandparents on cholesterol medications, such as Crestor™, Welchol™ or Lipitor™ I thought
you might be interested in information regarding the third member of the Cholesterol panel … the triglycerides. While most of us
may have heard of “good and bad” cholesterol … the triglycerides are a bit mysterious. Go share this with your folks or grandparents
Triglycerides: a type of lipid (fat) found in your blood
A Little Background About Fat:
As with most issues, there are good things and bad things about fat. The fatty acids of fats are good bio-chemicals! They
are used to build cells membranes, store energy, and are used like hormones (but they aren’t proteinaceous), as signaling
chemicals aiding in cell function. http://lpi.oregonstate.edu/ss08/fat.html
Normally, for us to utilize fat in food, complex lipids (fats) must first be hydrolyzed into smaller fatty acids, in the small
intestine.
The released fatty acids are absorbed by intestinal cells where they are converted to triglycerides (glycerol bonded to various
fatty acids). They are then packaged into lipoprotein particles called chylomicrons, [ki-low-my-krahns] which circulate in
the blood.
Hence, chylomicrons (often rich with triglycerides), are vehicles for the delivery of necessary fat to cells, via the bloodstream.
Enzymes, like lipoprotein lipase, on the surface of cells, degrade chylomicron lipids so that fatty acids can enter cells.
Once in cells, fatty acids are processed through various metabolic pathways, such as assembly into triglycerides for;
storage, assimilation into phospholipids for membrane synthesis, or oxidation in the mitochondria for energy production.
http://lpi.oregonstate.edu/ss08/fat.html
Triglycerides, Specifically
Triglycerides are one type of lipid (fat) found in your blood. There are two main sources of triglycerides: the diet and the
liver. As mentioned, previously, triglycerides are essentially a group of bio-chemicals produced by bonding glycerol to
various fatty acids http://lpi.oregonstate.edu/fw08/triglyceride.html
When you eat, your body converts any calories it does not need to use right away, into dietary triglycerides. The
triglycerides are stored in your fat cells (adipose tissue). Later, hormones release triglycerides for energy production,
required by our muscle tissues, between meals. http://www.mayoclinic.com/health/triglycerides/CL00015
The liver also produces triglycerides from both fat and carbohydrate. Hepatic (liver) triglycerides are then packaged into
very low-density lipoproteins (VLDL) and secreted into the blood, for delivery to various tissues for the production of
energy. Hence, VLDL are the lipoprotein particles formed to transport endogenously derived triglycerides to tissues.
http://lpi.oregonstate.edu/fw08/triglyceride.html
[Although triglycerides are energy rich, and used to store energy], chronically elevated triglyceride levels in the blood are
associated with metabolic syndrome, diabetes, and heart disease. Obesity, diabetes, a high-fat diet, and various genetic
conditions can cause elevated triglycerides. Food intake in excess of the body's need for energy exacerbates fat deposition
in adipose and muscle tissue, with possible detrimental health consequences. http://lpi.oregonstate.edu/fw08/triglyceride.html
Sources:
Jump, Donald B, WHAT'S GOOD ABOUT DIETARY FAT?
http://lpi.oregonstate.edu/ss08/fat.html
Moreau, Régis,
TRIGLYCERIDE-LOWERING PROPERTIES OF LIPOIC ACID http://lpi.oregonstate.edu/fw08/triglyceride.html
Mayo Clinic Staff TRIGLYCERIDES: WHY DO THEY MATTER? http://www.mayoclinic.com/health/triglycerides/CL00015
207
H H H H
| | | |
H―C―C―C―C―H
| | | |
H H H H
BUTANE
H―C  C―H
ETHYNE
FORMULA___________
H―C = C―H
| |
H H
ETHENE
FORMULA___________
PROPENE
FORMULA___________
H H
| |
H―C  C―C―C―H
| |
H H
BUTYNE
FORMULA__________
H H H
| | |
H―C―C―C―H
| | |
H H H
PROPANE
FORMULA___________
H H
| |
H―C―C―H
| |
H H
ETHANE
FORMULA____________
H H H H
| | | |
H―C = C―C―C―H
| |
H H
BUTENE
FORMULA____________
PROPYNE
FORMULA_____________
H
H
|
|
H―C = C―C―H
| |
H H
H
|
H―C  C―C―H
|
H
NAMING HYDROCARBONS
FORMULA: C4H10
Questions:
1) Define the terms:
alkane
alkene
alkyne
2) Each name has a
prefix and a suffix.
Upon what criterion
do we depend when
determining the
prefix & suffix for
the name of a
hydrocarbon?
208
D) Nomenclature HYDROCARBONS: Organic compounds that are made from ONLY C and H
1) For the simplest hydrocarbons: (aliphatic or straight carbon chain)
Every name has a prefix and a suffix. The prefix depends upon the * # of carbon atoms
and the suffix depends upon * the bonds
between the carbon atoms
(single, double, triple covalent)
Expanded Table Q: The Hydrocarbons
Examples
Formula
Name
Structure
Family
General
Formula
alkane
CnH2n+2
C4H10
butane
alkene
CnH2n
C4H8
1-butene
alkyne
CnH2n-2
C4H6
1-butyne
arene
(aromatic
hydrocarbon)
CnH2n-6
C6H6
Other Views
H H H H
| |
| |
H—C—C—C—C—H
|
|
| |
H H H H
H H
| |
H—C—C—C  C—H
|
|
|
|
H H H
H
H H
| |
H—C—C—C  C—H
|
|
H H
CH3CH2CCH
benzene
note: the term
aromatic refers to
a closed ring with
C or N with
alternating double
bonds
where "n" equals the number of carbons in the longest (parent) chain
Organic Prefixes
# of carbons
Prefix
1
meth
2
eth
3
prop
pron: prōp
4
but
(pron like beaut-y)
5
pent
6
hex
7
hept
8
oct
9
non
10
dec
12
dodec
(laur-yl)
16
Hexadec
(cet-yl or myrist-ic)
18
octadec (stear-yl)
20
eicos (arachid-ic)
Name the following compounds
C3H8 ______________________
(fuel for your gas grill)
C4H10 ______________________
(fuel of a BIC lighter)
C8H18 ______________________
(may be found in gasoline blends)
CH4
(natural gas used in some furnaces)
____________________
209
QUESTIONS ON HYDROCARBONS:
___1) Arithmetically speaking, the difference in formula between an alkane with three carbons, and one with four carbons
is that the latter molecule has
a) 1 more carbon and 1 more hydrogen
b) 2 more carbons and 2 more hydrogen
c) 1 more carbon and 2 more hydrogen
d) 2 more carbons and 1 more hydrogen
___2) Which pair represents two alkanes?
a) CH4 & C6H14
b) CH4 & C6H12
c) CH4 & C6H10
d) CH4 & C6H6
___3) Which pair represents two alkYnes?
a) C3H4 & C6H14
b) C4H6 & C6H10
c) C2H4 & C6H12
d) C2H4 & C6H6
c) C2H4 & C6H12
d) C2H4 & C6H6
___4) Which pair represents two alkEnes?
a) C3H4 & C6H14
b) C4H6 & C6H10
___5) Which compound is a member of the same family of hydrocarbon as C7H12?
a) C7H8
b) C9H18
c) CH4
d) C5H8
___6) Which compound has a double bond between carbons?
a) C7H8
b) C9H18
c) CH4
d) C5H8
7) Which will have more hydrogen, a five carbon alkEne or a 6 carbon alkYne? ____________________
8)
Name: C6H14 __________________________
9)
Name:
C2H4
__________________________
10) Name:
C5H12
__________________________
11) Name: CH3CH2CH2CH3 ____________________________
12) Draw the structural formula for C3H8
Answers: 1) c 2) a 3) b 4) c 5) d 6) b 7) neither one: they have the same number of hydrogen atoms 8) hexane 9) ethene 10) pentane
11) butane 12) Start by writing down 3 carbons. Connect them with bonds (―). Add 8 hydrogen so each C has only 4 bonds.
210
2) NON-HYDROCARBON COMPOUNDS: Organic Compounds with Functional Groups
Most organic compounds have special clusters of atoms, called functional groups, that
include atoms NOT FOUND hydrocarbon molecules. These functional groups give the
compounds particular properties. When an organic compound has S, O, N, or halogens, look
at Table R
211
Expanded / Alternate Version of Table R: Organic Compounds with Functional Groups
Class
Description
a
Examples of
molecular or
condensed formula
a
Alcohol
R-OH
(Monohydroxy)
1 (O-H) group
bonded to a carbon.
Soluble in water
(polar molecule)
a
C3H7OH
b
C4H9OH
Alcohol
(Glycol or
Dihydroxy)
Aldehyde
Ester
O
||
R—C—H
A carbonyl group on
a terminal C with
carbon or hydrogen as
the "R" group
O
||
R—O—C—R'
A product of an
alcohol & carboxylic
acid reaction.
Ketone
Carboxylic
Acid
(the most
common form
of organic acid)
Amine
(simple)
a
C2H4(OH)2
b
C3H6(OH)2
HCOH
b
CH3COH
a
CH3OOCCH3
b
C2H5OOCC2H5
O
||
R— C—R'
Has a carbonyl
group on an
"interior" or nonterminal carbon
O
||
R—C—O-H
Has a carboxyl
group (COOH)
bonded to a carbon.
RNH
|
H
A derivative of NH3
At least one H is
replaced with an
organic group. A
weak base (B-L)
a
C3H6O
b
C6H12O
CH3COOH
b
C2H5COOH
a
b
R-X
a
2-propanone (acetone)
Halogen(s) {X}
substituted onto a
hydrocarbon, by
removing hydrogen(s)
b
C3H6F2
ethanoic acid (acetic acid)
2-butanol
1,2-propanediol (propylene glycol)
H H H
| |
|
H—C—C—C—H
| |
|
H O-H O-H
b
ethanal (acetaldehyde)
H O
| ||
H—C—C—H
|
H
b
ethyl propanoate
H H
O H H
| |
|| | |
H—C— C—O—C—C—C—H
| |
|
|
H H
H H
b
3-hexanone
H H H O H H
| | |
|| | |
H—C—C—C—C—C—C—H
| |
|
| |
H H H
H H
b
H O
| ||
H—C—C—O—H
|
H
a
1-propanamine (1-propylamine)
H H H
| |
|
HCCCNH
| |
| |
H H H H
1-bromopropane
Br H H
| |
|
H—C—C—C—H
| |
|
H H H
Example / Structure
H H H H
| |
| |
H—C—C—C—C—H
| |
| |
H OH H H
H O H
| ||
|
H—C—C—C—H
|
|
H
H
C6H5NH2
C3H7Br
methanal (formaldehyde)
methyl ethanoate
H
O H
|
|| |
H—C—O—C—C—H
|
|
H
H
C3H7NH2
a
b
a
a
Halide
(or called:
halocarbon)
1,2-ethanediol (ethylene glycol)
O
||
H—C—H
a
a
b
H H
| |
H—C—C—H
| |
OH OH
a
a
1-propanol
H H H
| |
|
H—C—C—C—O-H
| |
|
H H H
a
2 O-H groups (or OH
groups ) bonded to
carbon. Soluble in
water (polar
molecule)
b
Example / Structure
propanoic acid
H H O
| | ||
H—C—C—C—O—H
| |
H H
b
phenylamine (aniline)
NH
|
H
b
1,2-difluoropropane
H H F
| |
|
H—C—C—C—H
| |
|
H F H
212
Try This: Give the correct IUPAC name of the following organic compounds
1)
6)
H H H H
| | | |
H―C―C―C―C―O-H
| | | |
H H H H
Class: ________________
Name: _________________
H H H H H
| | | | |
7) H―C―C―C―C―C―H
| |
| |
|
H H H H H
Class: __________________
Name: ________________
H H H H
| | | |
H―C―C―C―C―Br
| | | |
H H H H
Class: __________________
2)
H H H H H
| | | | |
H―C―C―C―C―C―H
| |
| |
|
H OH H H H
Class : ________________
Name: _________________
Name: _________________
3)
H H H H O
| | | | //
H―C―C―C―C―C―O-H
| | | |
H H H H
Class: __________________
8)
Name: _________________
Name: _________________
4)
H H H H O H H
| | | | ||
| |
H―C―C―C―C―C―C―C―H
| | | |
| |
H H H H
H H
Class: ___________________
9)
H
H H
|
|
|
H―C―C―C―C―H
| || | |
H O H H
Class: __________________
Name: _________________
Name: _________________
5)
H H H H H O
| | | | |
//
H―C―C―C―C―C―C―O-H
| | | | |
H H H H H
Class: __________________
O
//
H―C―O-H
Class: __________________
10)
Name: _________________
H H H
| | |
H―CC―C―C―H
|
| |
H
H H
Class: _________________
Name: _________________
Answers (for names)
1) 1-butanol
(every alcohol must have a number in the name to describe the position of the Carbon atom with the –OH functional group)
2) 1-bromobutane The number emphasizes which C has the Bromine (bromo) group
3) pentanoic acid Since the COOH groups are terminal (always on an "end"), no number is used in the name.
4) 3-heptanone This is a ketone. You need to have the numbered Carbon atom . Begin to count from the end nearest the functional group (in this case, then, begin counting from the right)
5) methanoic acid (also called formic acid .... The Genus of ants FORMICA was named for this chemical The ants inject it with every bite ...hence the FIRE ANTS are of the genus Formica!!!)
6) 2-pentanol
7) pentane
8) hexanoic acid
9) 2-butanone
10) 1- butene
213
E) Okay... Now take a minute to learn how to name some of those compounds with functional groups
There are a few observations to be made
1) Identification is pretty straight forward … ANALYZE the molecule and the reference tables.
2) You will see that the names all seem to be based upon the alkane names ....Yep!
3) THERE ARE PATTERNS TO NAMING THE 9 CLASSES OF ORGANIC COMPOUNDS
ON TABLE R
Compounds with a continuous C chain
Compounds without a continuous chain of C’s
Compounds in which
Compounds with terminal
Compounds in which the carbon chain is
the functional group
functional groups (the group
“interrupted” by atoms like N or O
can be on any C
must be on either the first or last C
of the parent chain
of the parent chain)
(longest chain of C atoms)
| | |
―C―C―C―
| |
|
O-H
or
| | |
―C―C―C―
| | |
O-H
note how the N breaks the C chain
|
H H O
| | ||
H―C―C―C―O-H
| |
H H
|
|
|
―C―C―N―C―
| |
|
H H H
H H
| | |
| |
H―C―C―C―O―C―C―H
| | |
| |
H H H
H H
214
II) Naming most other organic compounds is based upon the naming scheme used for the alkanes.
1) Name = Prefix match with a Suffix (You can get the suffix from Table R)
# of Carbons in
the longest chain
0
1
2
Prefix
alcohol
(drop the “e” from the
alkane name and add the correct
suffix)
The darn thing isn’t organic!!
methan
-ol
ethan
-ol
ketone
Not
Applicable
-oic
-al
-one
-oic
-al
(own)
3
propan
4
butan
5
pentan
6
hexan
7
heptan
8
octan
9
nonan
10
decan
organic aldehyde
acid
(ō-ic)
(ō-ic)
215
Name ___________________________________ ORGANIC CHEMISTRY: COMPOUND SUMMARY
A Wee Overview!
Organic Compounds
Properties
1) Must Have ____C___
2) Bond type = ___covalent_____
Hydrocarbons
Comps. with Functional Groups
Made only from atoms of __C&H___
Alkanes = __C-C______
sat.
CnH2n+2
3) Melting Point tends to be
lower than 150ºC
See Table __R___
These may be saturated or
unsaturated but they may
never be classified
as hydrocarbons
Alkenes = ___C=C_____
unsat w/ CnH2n
no free rotation around C=C e.g.) carboxylic acids
ketones
5) Tend not to conduct
esters
electricity when dissolved in water
Alkynes = ___C_≡ C_______
aromatics
(non-electrolytes) …NO + & - IONS
unsat w/ CnH2n-2
4) Tend to be insoluble in water
(not soluble)
exception: the carboxylic acids
6) Vapor pressure tend to be high: …tend to have an odor
lots of the molecules go into the gas phase due to
relatively weak attractive forces between molecules
7) Can undergo a number of
reactions: e.g. combustion, substitution, polymerization (slime…a.k.a. O’Leary or GFM) ...
8) When bonds between C atoms
are single then the molecule
is sometimes described as being __saturated_
When there is a double or triple
bond between C atoms then
the molecule may be described as being ___UNsaturated____
216