Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
2.1 Hydrocarbons
H H C H
saturated
H H C C C H C H C C H H
Methane An alkane
H C H C
H H
Ethene An alkene
Ethyne H An alkyne
Benzene An aromatic
2.1D Aromatics
In organic chemistry, aromatic has nothing to do with the
sense of smell. Compounds with benzene ring(s) are aromatic. There are other types of aromatics besides benzene derivatives (next semester). Bubblegum flavor is a mix of 3 aromatics:
cinnamon
vanilla
wintergreen
bonding electrons closer to one atom. This effect polarizes the bond; each atom has a partial charge (one positive, one negative). There are three ways to represent polar covalent bonding:
Partial
CO
and negative charge. of positive distribution Blue = positive; red = negative The spherical shape of the map around the nuclei represents electron density.
polarities.
The 4 bond polaritiesc cancel out.
The CCl bond polarity gives rise to the dipole moment. The CH bond dipole is minor and insignficant.
+ + + + + + + + + + + + +
placing a sample between 2 oppositely charged plates. Samples with non-zero dipole moments conduct a current because their positive and negative sides line up along the plates.
charged plates so that one side of the molecule is positive and one is negative.
indicate how a molecule reacts; e.g., the alcohol FG has a C-O-H linkage and all alcohols react similarly.
ALCOHOLS
H H C H H C H
HO
OH
OH
ethanol
cholesterol
menthol
indicate how a molecule reacts; e.g., the alcohol FG has a C-O-H linkage and all alcohols react similarly.
ALCOHOLS ALCOHOL in oxidation strong acid base
H H H C H H C C
H H H
H H H
H
+-
C O O C O OH
H H
H
H
H O+ O O O
-
with yl The H atom that is removed is substituted with another atom or group. H H
H H C H
H C H
H C H
H C OH H
Cl
C H
NH2
ethane
H H C H H C H H C H H H
ethyl group
H C H H C H H C H H H C H H C H C H H
propane
propyl group
isopropyl group
H
C C
H C
CC C C HH C C C C CH H 2
C
C C
CH2 ? ? C
Bn Ph ??
CC C C HH H H
C
H
methylbenzene benzene
F, Cl, Br or I (halogens or X)
Alkyl halides are classified as methyl, primary (1),
secondary (2) or tertiary (3). Consider the C atom directly attached to the halogen (CX) and determine how many C atoms are attached to CX.
H H C H
H C H
H C Cl
H C H
2
H H
I C H H
C H H
H Br C H
H C H
H C H
H C H H
2.6 Alcohols
The alcohol functional group is a hydroxyl (OH) group
attached to an sp3-hybridized carbon. Just like alkyl halides, alcohols are classified as methyl, primary (1), secondary (2) or tertiary (3).
2.6 Alcohols
What is the degree of substitution (methyl, 1, 2 or 3)
1 H
OH
H C H
H C H OH
H H C H
F C
H
HO
OH H
2.7 Ethers
Ethers have oxygen atoms bound to two carbons. The groups bound to oxygen can be alkyl or phenyl. Since they are so unreactive, ethers make good
solvents.
2.8 Amines
Amines have one or more alkyl groups attached to
N C
N C
2 amine
3 amine
molecular geometry. The amine N is sp3-hybridized; most amine chemistry occurs at the lone pair.
trimethylamine
O C
carbonyl subgroup
O C
carbonyl subgroup
the other atom can be H (formaldehyde) or C. Ketones have two carbons bound to the carbonyl group. Aldehydes and ketones are grouped together because they have similar reactivity.
O C H H/C
O C C
ketone
aldehyde
grouped together because they are all interconvertible by simple chemical reactions.
O C H/C O H H/C O C O C
H/C O C N
carboxylic acid
ester
amide
O
O
-
F C F F
F C F F
C O
+ H+
The pKa of trifluoroacetic acid (above) is 0.23. pKa (H3PO4) = 2.15; pKa (HCl) = -2.2.
+ ROH
R
C OR'
+ H2O
carboxylic acid
ester
2.10C Amides
Amides are commonly formed by reaction of
+ NHRR
amine
C R N R'
R"
carboxylic acid
amide
alkynes.
H H C H C N
CN
O
CN
ethanenitrile
benzonitrile
cyanoacrylate
CH NH OH H3 H H H H H H H H OCH 23
ester alkyl carboxylic halide aromatic aldehyde ketone alkane alkene amine alkyne amide nitrile or haloalkane acid
Boiling point
Solubility
2. Hydrogen bonding
3. Dispersion forces (instantaneous dipole)
Blue = d+ Red = d-
Small; molecules can approach closely Very electronegative; strong partial charges on H and X
O C H N H H H
O C N H CH3
O C H N CH3
CH3
Which of these has the highest153 boiling point? 210 C compounds 198
H Bonds:
and ions Caused by temporary buildup of charge at one part of a particle (instantaneous dipole) that in turn induces a dipole in its neighbor. Responsible for liquid and solid phases of nonpolar molecules.
2.13D Solubility
Will solute A dissolve in solvent B? Like dissolves like If A is ionic, YES if strong ion(A) - dipole(B) interactions If A is polar covalent, YES if strong dipole(A) - dipole(B) interactions If A is nonpolar covalent, YES if B is nonpolar.
O HO CH3
HO
4-5 6+
O
Moderate Low
HO
O
OH OH
H H C H F
O
CH3
HO
Cl
CH3
HO HO O H
Yes
No
Kind of
Yes
No
groups, not its entire structure. Most organic molecules absorb IR radiation. IR absorptions produce transitions from low to high vibrational levels within molecules. DE(Absorption of an IR photon) 1 10 kcal/mol It takes < 1 min to acquire an IR spectra.
corresponding to FGs. percent transmittance ( absorbance). y-axis: The fingerprint region is 1300 - 400 cm1 and is unique to every compound.
(mid-IR region)
H H C H OH
C H
OH
2.15 IR Absorptions
DE = hn
wavenumber (increasing, decreasing) energy. A (triple, double, single) bond is the strongest bond. The highest wavenumbers are required to vibrate a (triple, double, single) bond.
spectrum since they are generally weaker bonds. H-X bonds appear on the left because hydrogen has the smallest mass.
CC
C=C
CC
CH3 H CH3
CCH
C=CH
CCH
only its functional groups. Most of the peaks on an IR spectrum are not useful. To interpret an IR, consider what FGs may be present in the molecule (based on molecular formula) and look for their characteristic peaks.
carboxylic ketone aldehyde acid (CH [CH (CH (CH CHO) ) ) CO ester amide (CH [HCON(CH CCO CH )2 ]) 2H] 3COCH 3 3 2CH 34 2 2CH 2 3 3
H C C H H C H
propane C3H8
C H
cyclopropane C3H6
propene C3H6
propyne C3H4
O, S: just ignore them. Halogens: convert them to H. N: subtract 1 H, then ignore them
is its IHD?
O C H
2.16 IR
following IR. What is the compound?
C H
C=O
# rings/multiple bonds = 1
2.16 IR
CH3(CH2)3CCH
# rings/multiple bonds = 2
OH
alcohol
phenol
themselves:
R H O C R O H O C O
counting the number of (medium-sized) peaks in the 3300 3500 cm-1 region.
H 2 H-bonds 2 peaks
C 1 H-bonds 1 peaks
C 0 H-bonds 0 peaks
CH3(CH2)9NH2 NH2CH2CH2CH2NH2
2.15B IR
What is a possible structure for a compound with
# rings/multiple bonds = 2