Organic chem Flashcards
Why is organic chemistry largely carbon compounds (2)?
1- carbon’s unique ability to form strong covalent bonds with itself
2- carbon’s ability to form 4 covalent bonds
How do we classify compounds?
based on their chemical properties: FUNCTIONAL GROUPS
What is the functional group of alkanes and an example?
No functional group
Ethane
What is the functional group of alkenes and an example?
Double bonded C
Ethene (or ethylene)
What is the functional group of aromatics and an example?
Bonded C ring with alternating double/single bond
Toluene
What is the functional group of alkynes and an example?
Triple bonded C
Ethyne (or acetylene)
What is the functional group of halides and an example?
C bonded to a halogen
Chloromethane
What is the functional group of ethers and an example?
-C-O-C-
dimethyl ether
What is the functional group of alcohols and an example?
-C-OH
Methanol
What is the functional group of amines and an example?
-C-N-
Methylamine
What is the functional group of aldehydes and an example?
O=-C-H
Ethanal (or acetaldehyde)
What is the functional group of ketones and an example?
O=-C-C
Propanone (or acetone)
What is the functional group of carboxylic acids and an example?
=O-C-OH
Ethanoic acid (or acetic acid)
What is the functional group of esters and an example?
=O-C-O-C
Methyl ethanoate (or methyl acetate)
What is the functional group of acid chlorides (or acyl chlorides) and an example?
O=-C-Cl
Ethanoyl chloride (or acetyl chloride)
What is the functional group of amides and an example?
O=-C-N
Acetamide
What are hydrocarbons?:
simplest organic compounds containing only C and H
What are saturated hydrocarbons?
contain only C–C bonds & therefore max. # of H atoms per carbon atom
What are the two classes of saturated hydrocarbons?
- Alkanes
- Cycloalkanes
What is the formula for alkanes and examples?
CnH2n+2 where n = 1, 2, 3, …
methane, ethane, propane
What happens when an alkane has more than 3 carbons?
isomers are possible and the number of isomers increases dramatically as the number of carbons increase
What are 3 components to the IUPAC system of nomenclature?
- Parent – longest chain
- Substituents – groups attached to chain
- Numbers – used to identify position
How to name alkanes based on numbers of IUPAC
- Locate longest chain and number each carbon beginning at the end nearest to substituents. 2. Name chain based on the number of C’s.
- Indicate the positions of each substituent based on numbers assigned to C’s in chain.
- If the same substituent occurs more than once, indicate the frequency by using prefixes:
di- (2), tetra- (4),
tri- (3), penta- (5), etc.
and the position number of each substituent. - List substituents in alphabetical order (ignoring the prefixes, di-, tri-, tetra-, etc.)
- Punctuation:
words are not separated
a word and number are separated by a hyphen
two numbers are separated by a comma
What are some factors about cyclohexanes?
saturated hydrocarbons having a ring of carbon atoms.
group formula: CnH2n
prefix “cyclo” added to parent name
no number is needed for a monosubstituted cycloalkane.
if more substituents, number the ring’s carbons to achieve the smallest # for the substituents.
in more complex compounds, a cycloalkane ring can be treated as a substituent.
What is the formula for Alkenes?
CnH2N
(R)2–C = C–(R)2
What is the formula for Alkynes?
CnH2n-2
R – C — C – R
What is the nomenclature for alkenes and alkynes?
identify longest chain containing double or triple bond.
number carbons starting with end closest to the double or triple bond.
parent name uses “ene” or “yne” instead of “ane”.
position of double or triple bond indicated by a number preceding the parent name. indicatesubstituentsasusual.
What are aromatic hydrocarbons?
derivatives of the compound benzene
What is the nomenclature of benzene derivatives (aromatic hydrocarbons)?
- no number necessary for monsubstituents, use common names, e.g., toluene, phenol and benzoic acid
- three isomers possible for disubstituents:
1,2- ortho or “o”
1,3- meta or “m”
1,4- para or “p” - when 2 substituents are different, compound named as a derivative of a monsubstituted benzene, i.e., o-chlorotoluene.
- when more than 2, use numbers to identify positions: 3,5–dimethylphenol
What are organic halogen compounds?
hydrocarbons with halogen substituents
- haloalkanes or alkyl halides
- aryl halides
classified as 1, 2, or 3 according to its C
nomenclature:
F fluoro
Cl chloro
Br bromo
I iodo
EX: CH3CH(Br)CH2Br 1,2-dibromopropane
What are ethers?
derivative of water (HOH)
structures: R-O-R, R-O-Ar, Ar-O-Ar
ether group treated as substituents
EX:
CH3–O–CH2CH3 methoxyethane (common name: ethyl methyl ether)
CH3CH2–O–CH2CH3 ethoxyethane (common name: diethyl ether, also known as “ether”)
What are alcohols and phenols?
hydrocarbons with a H atom replaced by OH
alcohols symbolised by ROH, phenols by ArOH
What is the nomenclature of alcohols and phenols?
- locate longest chain containing –OH 2. number giving lowest # to –OH group 3. “ane” ending becomes “anol”
- give number of –OH position
- substituents named before parent
- an alcohol is classified according to the C it’s attached (i.e., 1, 2, or 3)
What are amines?
derivatives of ammonia (i.e., NH3)
structures: R-NH2, Ar-NH2, R2NH or R3N
characterised as 1 , 2, or 3.
distinct odor
aliphatic in nature (acid-base chemistry)
What group do aldehydes and ketones both contain?
carbonyl (end in aldehydes, middle in ketones)
What is the nomenclature for aldehydes?
number longest chain containing carbonyl.
carbonyl carbon is number 1.
group ending: “anal” (i.e., butanal)
What is the nomenclature for ketones?
number longest chain containing carbonyl
begin numbering closest to carbonyl group
indicate position of carbonyl group with # preceding the parent name
group ending: “anone” (i.e., butanone)
What group do carboxylic acids and derivatives have?
hydroxyl bonded to acyl
replacement of hydroxyl group with substituents in derivatives
What is the nomenclature for carboxylic acids and derivatives
- number longest chain with acyl group 2. acyl group understood to be position #1
- group ending: alk|ane
|anoic acid -carboxylic acid (contain –COOH group)
|anoate -ester and salt (contain –COOR or –COO–M+ group)
|anamide -amide (contain –COONR2 group)
|anoyl chloride -acid chloride (contain –COCl group) - name and number substituents in front
How do you distinguish between primary, secondary, and tertiary carbons?
primary (1) – carbon attached to 1 other carbons (i.e., a terminal carbon)
secondary (2) – carbon attached to 2 other carbons
tertiary (3) – carbon attached to 3 other carbons
What are structural/constitutional isomers and the 3 types ?
- same molecular formula but different order of the atoms (i.e., different names)
Skeletal, Positional, Functional
What are isomers?
molecules with the same molecular formula
What are skeletal isomers?
different arrangements
What are functional isomers?
different functional groups
What are positional isomers?
different position of substituents
What are cis-trans isomers?
CIS- indicates that the substituents are on the same side of the double bond or ring
TRANS- indicates that the substituents are on the opposite sides of the double bond or ring
Effect of cis-trans isomers on properties
different melting points, boiling points, density and other physical properties
What are optical isomers?
chiral compounds
What are enantiometers?
non-superimposable mirror images
Do optical isomers have the same properties?
Identical physical and chemical properties EXCEPT for the sign of the ROTATION
What are the 4 types of Intermolecular forces, their interacting species, and the energy (kj/mol)?
Ion-Ion -> only ions -> 250
H bonding -> only hydrides of N, O, F; the link is a shared H atom -> 20
Dipole Dipole -> polar molecules -> 2
London (dispersion) -> all molecules -> 2
Describe London forces
- strength increases with higher molar mass
- between all molecules (N-P)
Describe Dipole-Dipole
- attractive forces between the positive end of one polar molecule and the negative end of another polar molecule
Describe Hydrogen bonding
- between H bonded to F, N, O
What are the strongest to weakest intermolecular forces
H-bonding > Dipole-Dipole > London Dispersion
When do B.P. and water solubility increase?
with the strength of the intermolecular forces and the number of functional groups that generate these forces (like dissolves like)
How does branching of the alkane affect the B.P.?
lowers the B.P. due to less ordered packing
What does an increase in chain length have an effect on B.P. and water solubility?
leads to an increase in b.p. but a decrease in water solubility
What is an electrophile?
a positive species that accepts electrons
(i.e., Lewis Acid) e.g., H+ likes to attack a bond
What is a nucleophile?
a negative (e.g., OH–) or neutral species (e.g., H2O or CH3OH) wanting to donate a pair of electrons to a positively charged carbon near an electronegative species, like a halogen (i.e., Lewis Base).
What are free radicals?
a neutral species having an extra electron, e.g., Cl
What are the sites for nucleophilic attacks?
positive dipole
What are the sites for electrophilic attack?
pi bonds
What are reaction intermediates
species that are produced and consumed during a reaction but CANNOT BE ISOLATED and do not play a role in the overall chemical equation
Are alkanes reactive?
No, due to strength and non-polar nature of bonds
What are the chemical properties of alkanes?
inert to common strong acids (e.g., H2SO4, HCl)
inert to common strong bases (e.g., NaOH)
inert to oxidising agents (e.g., MnO4– & Cr2O72–)
inert to reducing agents (e.g., Na)
* chemistry of alkanes involves free radicals
What are the three types of alkane reactions?
pyrolysis, combustion, halogenation
What is a pyrolysis reaction (or cracking)?
decomposition of compound by heating usually in presence of a catalyst
What is a combustion reaction?
burn in the presence of O2