Transcript CH 3

Honors Chemistry
Ch. 22 Organic Chemistry
USNCO & IChO
U.S. National Chemistry Olympiad local competition (CHS) – 1st Saturday morning
in March (MC exam)
National competition (Indpls) – a Saturday in April (MC, FR, and lab exams)
USNCO – top 20 students (USAF, Colorado Springs) – 2 weeks in June
IChO – July 20-29, 2014 in Hanoi, Vietnam
Organic
pertaining to carbon
compounds
Organic Molecules
carbon compounds with
these exceptions:
•no carbon oxides
•no carbonate ions
•no cyanide ions
•no carbon disulfide
Organic Compounds
insoluble in water
low melting points &
boiling points
decompose
easily
combustible
Hydrocarbons
molecules made up of
hydrogen and carbon.
Fossil fuels
Molecular Formula: C H
4 8
shows numbers of atoms
Empirical Formula:
CH2
shows ratio of atoms
Structural Formula:
HHH
shows location H-C-C-C=C-H
of atoms
HH
H
Condensed
Structural Formula
Lists H after the C atom
to which it is bonded.
Only carbon to carbon
bonds are drawn.
# of Carbons in Chain
methethpropbutpent-
1
2
3
4
5
hex-
6
hept- 7
oct- 8
non- 9
dec- 10
Alkane
a hydrocarbon
containing only single
bonds
Names of Alkanes
Start with the root for the #
of carbons in the chain
Suffix:
“-ane”
Alkane General
Formula
CnH2n+2
# H atoms =
2 • (# C atoms) + 2
Saturated
hydrocarbon chain
containing as many
hydrogens as it can hold
an alkane
Alkene
a hydrocarbon containing
at least one double bond.
Name ends with “ene”
Alkyne
a hydrocarbon containing
at least one triple bond.
Name ends with “yne”
Name these:
CH3-CH2-CH2-CH3
butane
CH3-CH=CH-CH3
2-butene
CH3-CH2-C=CH
1-butyne
CH3-CH2-CH=CH-CH2-CH3
3-hexene
CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3
octane
Branched
Hydrocarbons
a carbon atom bonded to
three or four carbon
atoms
Branched
Hydrocarbons Names
1. Name the longest
carbon chain (called the
parent chain)
propane
CH3
CH3-CH -CH3
Branched Hydrocarbon
Names
2. Name the short branches
using the suffix “-yl”.
(“meth-” becomes “methyl”)
CH3
CH3-CH -CH3
Branched Hydrocarbon
Names
3. Number the carbons on
the parent chain, starting
with end closest to
branch(es).
CH3
1
2
3
CH3-CH -CH3
Branched HC. Names
4. Put together
•# of carbon with branch
•-branch name
•Parent chain name
2-methylpropane
Review #1:
Alkane
single bonds
double bond
Alkene
Alkyne
triple bond
Review #2:
Name the compound
represented by the
following condensed
structural formula:
CH3
CH3-CH2-CH -CH3
Answer:
2-methylbutane
CH3
CH3-CH2-CH -CH3
Review #3:
Name the compound
represented by this
condensed structural
formula:
Answer:
3,5,5-trimethyl-3heptene
Review #4:
Draw a condensed
structural formula for:
3,3,4,4-tetramethyl-1hexyne
Answer:
3,3,4,4-tetramethyl-1hexyne
CH2-CH3
CH3-CH2-CH2-CH2-CH-CH2-CH3
3-ethyl heptane
CH3-CH2-CH=CH-CH3
2-pentene
CH3-CH2-C=C-CH3
2-pentyne
Cyclic Alkanes
Cyclohydrocarbons
Hydrocarbons that contain
a ring.
Names: add “cyclo-” just
before the ring name.
Benzene
C6H6
aromatic ring (alternating
single, double bonds) of 6
carbon atoms
Benzene resonance
structure:
Conformations
Organic molecules that
differ from one another
only by rotated bond(s)
Structural Isomers
Molecules with the same
numbers of atoms, but
different bond
arrangements.
Stereoisomers
Same atom-to-atom bonds,
but different locked
orientations
Double bond prevents
rotation.
2 orientations: cis(same side)
& trans (opposite side)
I:
cis-1,2-dichloroethene
II: trans-1,2-dichloroethene
Polymers
large organic
compounds made up of
repeating units
“poly” = many
“mer” = parts
Functional Groups
any element or group that
replaces hydrogen on a
hydrocarbon.
Halocarbons: R-X
functional group on a
hydrocarbon is a halogen
(“X”).
Halocarbon Names
# of carbon where halogen
is bonded
Halogen name with “o”
replacing “ine”. (“chloro”
for Cl)
Parent chain name
CH2F-CH2-CH2-CH3
1-fluorobutane
CH3-CCl2-CH2-CH3
2,2-dichlorobutane
CHBrCl-CH2Br
1,2-dibromo-1-chloroethane
CH2Cl-CHCl-CH2-CH3
1,2-dichlorobutane
CH2F-CHBr-(CH2)4-CH3
2-bromo-1-fluoroheptane
CHClF-CH2-CHF-CH2-CH3
1-chloro-1,3-difluoropentane
Alcohols: R-OH
have an -OH functional
group called a hydroxyl
group.
Parent chain suffix
replaced by “-ol”
Types of Alcohols:
Primary: C of the -OH group is
bonded to one other carbon
Secondary: C-CHOH-C bonded
to 2 other C’s
Tertiary: C of the -OH group is
bonded to three
other carbons
CH2OH-CH3
1-ethanol
CH3-CH2-CHOH-CH3
2-butanol
Carboxylic Acids:
-COOH functional group
called a carboxyl group.
Parent chain suffix replaced
by “-oic acid”
O
CH3-COOH or CH3-COH
Ethanoic acid