Organic Flashcards
alkanes
(-ane) CnH2n+2
non polar, London dispersion
few reactions
water insoluble
Alkenes
(-ene) CnH2n
double bond
non polar, insoluble in water
unsaturated
Alkynes
(-yne) CnH2n-2
triple bond
non polar, insoluble in water
Benzene
Aromatic compound. Each is trigonal planar (120 degrees), low mp and bp, water insoluble
ortho (o)
1,2
meta (m)
1,3
para (p)
1,4
Alcohols
(-ol)
Contain OH (hydroxyl) group
polar, dissolve in water (OH is hydrophilic)
ethers
ROR, 2 alkyls bonded to O polar, net dipole dipole dipole interaction soluble in organic solvents 5 C or less= soluble in water
nitrogen has __bonds, and __ number of unbounded electron pairs
3 bonds
1 lone pair
oxygen has __bonds, and __ number of unbounded electron pairs
2 bonds
2 lone pairs
halogens have __bonds, and __ number of unbounded electron pairs
1 bond
3 lone pairs
Halogens = F, Cl, Br, I
saturated hydrocarbons contain ____
the maximum number of hydrogen per carbon
the removal of a ___atom from an alkane results in the formation of an ___ group.
hydrogen atom,
alkyl group
-CH3
methyl
-CH2CH3
ethyl
-CH2CH2CH3
propyl
-CH2CH2CH2CH3
butyl
CH2CH2CH2CH2CH3
pentyl (or amyl)
branched alkyl groups
are formed by removing a hydrogen atom from an internal carbon
constitutional isomers have ___ physical and chemical properties
different
systemic name for drugs
follows the IUPAC rules
generic name for drugs
the official, internationally approved name for the drug (ibuprofen)
trade name for drugs
the name assigned by the manufacturing company (Advil)
highly branched molecules have a ____boiling point because of ____ surface area
lower boiling point because of smaller surface area
complete combustion of alkanes forms
CO2 and H2O and energy
incomplete combustions of alkanes forms
CO and H2O and energy
unsaturated hydrocarbons
contain fewer than the maximum number of hydrogen atoms per carbon
why do cis and trans stereoisomers of alkenes occur?
double bonds do not exhibit a free rotation at room temperature
cis stereoisomer
exhibit identical groups on the same side of the double bond
trans stereoisomers
have identical groups on the opposite sides of a double bond
difference between constitutional isomers and stereoisomers
stereoisomers differ in the 3D arrangement of atoms,
constitutional isomers differ in the way the atoms are bonded to each other.
commonly used birth controls drugs (ethynylestradiol and norethindrone) are….
similar to the female sex hormones estradiol and progesterone, but they contain a C-C triple bond. They inhibit the release of LH and FSH
the product of hydrogenation is…
an alkane
hydrogenation
addition of H2 to an alkene, with the metal catalyst palladium (Pd)
during addition reactions, the OH group is added to the carbon that….
makes the molecule the most stable, tertiary carbon (3rd degree).
polymerization: the side that contains the substituent is called the
head
the monomer has a …
double bond
nomenclature of benzene
name the subsistent and add the word Benzene, or name of common root.
-only two substituents: use the descriptors o, m, p
-more than two, alphabetize.
If substituent is a halogen: change the suffix to -o.
nitration
mixture of sulfuric acid (H2SO4) and nitric acid (HNO3), causes the ring to undergo nitration to form an electrophile called nitronium (NO2+).
fuming acid
H2SO4 and SO3 gas
sulfonation
when benzene is treated with fuming sulfuric acid, and benzene-sulfonic acid is produced (benzene + attached SO3H).
Sulfur trioxide (SO3) is a very powerful…
electrophile
many phenols serve as….
antioxidants, to prevent unwanted oxidation reaction from happening in the body.
isobutyl alcohol =
2-methyl-1-propanol
isopropyl alcohol =
2- propanol
ethers with larger alkyl groups have __ boiling point, due to _____ forces
higher boiling point
London dispersion forces
ethanol
CH3CH2OH
name of first general anesthetic
diethyl ether
dehydration
occurs when an alcohol is treated with a strong acid and forms an alkene product and water product
(elimination reaction- starting material “lost”)
primary alcohol oxidation
first oxidize to aldehydes, and then to a carboxylic acid
Possible oxidizing agents: chromic acid, acidic dichromate or KMnO4.
secondary alcohol oxidation
oxidize to ketones
tertiary alcohol oxidation
no oxidation occurs
Blood alcohol screening
oxidation of ethanol with K2Cr2O7 is characterized by a color change, the red-orange reagent is reduced to a green Cr3+ product
what enzymes break down alcohol in the liver?
alcohol dehydrogenase and aldehyde dehydrogenase
thiols can be oxidized to…
disulfides
disulfides can undergo a reduction reaction to form…
thiols
aldehydes
“al” ending
polar
soluble in organic solvents
insoluble in water
ketones
“one” ending
polar
soluble in organic solvents
insoluble in water
acetone
both R groups are CH3
formaldehyde
2 H’s on the Carbonyl group
cyclic ketones nomenclature
carbonyl croup is “1” (omitted), the numbered to give the first substituent the lowest number
aldehydes are oxidized to ____ in the presence of ___
carboxylic acids in the presence of potassium dichromate (K2Cr2O7).
H to OH
ketones oxidation
ketones do not undergo oxidation.
tollens reagent
silver (I) oxide (Ag2O) in aqueous ammonium hydroxide (NH4OH).
a nonidentical mirror image is called…
an enantiomer
optically active means
it is able to turn polarized light
a chiral molecule is optically active
counterclockwise vs clockwise when configuring a sterocenter
counterclockwise = S clockwise = R
carboxylic acid
“-oic acid”
polar
esters
“ate”
polar
carboxylic acids react with bases to form…
water-soluble salts
NaOH
ester formation
carboxylic acids react with alcohols in the presence of an acid to form esters
ester hydrolysis
and ester with water in the presence of an acid to form a carboxylic acid.
saponification
esters are hydrolyzed in aqueous base to form carboxylate anions an a molecule of alcohol.
amines with the N directly bonded to a benzene ring are names as derivatives of ….
aniline
use prefix N-
amines
polar
water insoluble
amines are ___ and proton ___
bases, proton acceptors
amines react with acids to form
water soluble salts
ammonium slats (positively charged)
acid forms an anion
to name ammonium salts
name the amine
change suffix to ammonium
add name of anion
CH3COO- is called
acetate
amines can react as nucleophiles with…
alkyl halide through substitution reactions
treatment of an amide with water in the presence of an acid catalyst forms…
a carboxylic acid and ammonium salt
amides are hydrolyzed in an aqueous base to form..
carboxylate anions and a molecule of ammonia NH3
aspirin and ibuprofen are ____ agents that contain ____
anti-inflammatory
carboxyl group (COOH)
blocks the synthesis of prostaglandins (responsible for pain)
