Chemistry: Organic Chemistry Flashcards
Aromatic character is denoted by ________.
Having conjugated pi bonds in resonance, allowing for more stability
A compound that contains an EDG in the ring is (more/less) aromatic than a compound that contains an EWG (EN).
More
______ is present in drinks and has a concentration as high as 45%. It destroys brain cells and inhibits protein synthesis in the heart, damages the liver, causes nausea, sweating, and rapid heartbeats, and decreases blood pressure
Ethanol
The Markovnikov’s rule (esp. for addition of halogens as HX) states that X bonds with the atom that is (more saturated/less saturated) with hydrogen.
Less saturated
If a compound rapidly decolorizes in a solution of bromine in an inert solvent, the compound is _______.
Unsaturated
Ozonolysis, which uses O3 to uncleave unsaturated compounds, replaces unsaturated bonds with __________.
Double bonds with oxygen
Grignard reagent is (nucleophilic/electrophilic) and when added to CO2, _______ is formed after acidification.
Nucleophilic, carboxylic acid
Process involving conversion of fat, oil, or lipid into soap and alcohol by action of aqueous alkali
Saponification
Chemical process by which an alkyl group is attached to an organic substrate molecule via addition or substitution
Alkylation
Process of combining an organic acid (RCOOH) with an alcohol (ROH) to form an ester (RCOOR) and water
Esterification
If the value of K is (greater/less) than 1, the products in the reaction are favored. If the value of K is (greater/less) than 1, the reactants in the reaction are favored
Greater, less
Ratio of the equilibrium concentrations of products over the equilibrium concentrations of reactants each raised to the power of their stoichiometric coefficients
Kc
If all coefficients of the equilibrium equation are divided by 2, the Kc is decreased by what factor
By square root of the Kc
Seven metalloids
Boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), tellurium (Te), and polonium (Po)
(T/F): An element melts at a definite temperature.
TRUE.
(Metals/metalloids/nonmetals) have high MP, good conductors of elec/heat, high density, malleable, ductile, solid at room temp
Metals
Oxides that combine with metals form _____ whereas oxides that combine with nonmetals form _____. (Acids/bases)
Bases, acids
Only metal which is liquid at room temperature
Mercury
(T/F): All metals are hard.
FALSE.
(T/F): All metals can combine with oxygen easily.
FALSE.
(T/F): All metals are good conductors of heat and electricity.
TRUE.
Scattering of a beam of light by a medium containing small suspended particles
Tyndall effect
Higher vapor pressure (higher/lower) the amount of pressure exerted on the liquid by the atmosphere, resulting in (higher/lower) boiling point.
Lowers, lower
Entropy (increases/decreases) total number of product molecules is greater than the total number of reactant molecules, except when nongaseous products make a gaseous product.
Increases
Haloalkanes are heated with aqueous _______________ to form alcohols.
Sodium or potassium hydroxide
Organic compounds are mostly soluble in (polar/nonpolar) solvents like hexane and ether.
Nonpolar
Organic compounds are (usually/not usually) combustible and flammable.
Usually
Region in space about the nucleus where electrons are located; mostly described as electron clouds
Atomic orbital
(S/p) orbitals are spherical in shape whereas (s/p) orbitals are dumb bell shaped
S, p
Orbitals that are in the same energy level; describes the 3 p orbitals
Degenerate
Mixing or overlapping of orbitals
Hybridization
Head to head overlap of orbitals are called _____ whereas lateral/sideways overlap form ________; which of the two are weaker?
Sigma bonds, pi bonds; pi bond (presence of node or 0 e- density)
Type of hybridization associated with trigonal planar; number of sigma and pi bonds
sp^2; 3 sigma and 1 pi bond
What functional group is characterized by R-O-R; how is it named?
Ethers; [smaller]oxy[bigger] or [smaller] [bigger] ether
What functional group is characterized by R-SH? How is it named?
Thiol; [parent]thiol & mercapto- as a substi
What functional group is characterized by R-S-R?; how is it named?
Thioether; -thioether or [parents] sulfide
What functional group is characterized by R-C=OH; how is it named?
Aldehyde; -al
What functional group is characterized by R-C=O-R; how is it named?
Ketone; -one
What functional group is characterized by R-COOH; how is it named?
Carboxylic acid; -oic acid
What functional group is characterized by R-COX; how is it named?
Acid halide; -oyl halide
What functional group is characterized by R-C=O-O-C=O-R; how is it named?
Acid anhydride; [parent]oic [parent]oic anhydride, includes carbonyl C
What functional group is characterized by R-C=O-OR’; how is it named?
Ester; [alkyl] [alkanoate]
alkanoate is the one connected to the C=O (not OR’), includes carbonyl C
What functional group is characterized by R-N; how is it named?
Amine; -amine
What functional group is characterized by R-C=O-N; how is it named?
Amide; -amide
Attachment of atoms (usually E & Nu) to a substrate; typically involves breakage of a double bond (A=B + E-Nu –> EA - BNu)
Addition
Removal of atoms (usually E & Nu) from a molecule (adjacent carbons); leads to formation of double bond
Elimination
Joining of two molecules together with the elimination of small molecules such as water. Usually involves a _____ and a functional group with reactive H like alcohols or amines (e.g. esterification)
Condensation; carboxylic acid
Replacement of one atom/group in a substrate with another atom or functional group
Substitution
Increase in bonding with oxygen atom and/or decrease in bonding with hydrogen atom; brought about by _____ agents (which are oxygen-rich) like strong acids
Oxidation; oxidating agents
_______ agents are hydrogen-rich, and include ______ reagent (NH2NH2 in KOH) and ______ reagent (zinc amalgam; Zn/Hg in HCl)
Reducing; Wolff-Kishner; Clemmensen
Cycloalkanes are function isomers of (alkanes/alkenes/alkynes).
Alkenes (general formula CnH2n)
(Isobutyl/tert-butyl) uses itself for alphabetization but (isobutyl/tert-butyl) uses butyl.
Isobutyl, tert-butyl
Carbon atoms in a molecule are classified as 1º, 2º, 3º, and 4º according to the number of _____ atoms that are bonded to it.
Carbon
Alkanes are usually (inert/reactive).
Inert
Heating in the absence of oxygen to breakdown larger alkanes into smaller ones (e.g. C6H14 –> C4H10 + C2H4)
Pyrolytic cracking
Addition of halogen to alkanes (reagent: Cl2 or Br2) as catalyst by light (UV) which occurs via free radical mechanism; for alkenes, occurs in a dark room at room temp in inert solvent to give a vicinal dihalide
Halogenation
Product of halogenation of alkanes is a mix of ________ and the predominance is (1º>2º>3º / 3º>2º>1º)
Alkyl halides, 3º>2º>1º
Type of isomerism where bonded groups exist in different orientation in space
Geometric isomerism
For a __substituted alkene, cis- and trans- are used to indicate whether the attached groups are located on the same or opposite sides.
Di
(Cis/trans) alkenes are more stable but (cis/trans) alkenes have higher boiling points
Trans, cis
The __________ is used in determining the geometric isomerism of tri and tetra substituted alkenes.
E/Z designation
In the E/Z designation, when high priority groups (based on MW) on each side are at the same side, then it’s designated as (E/Z) isomer.
Z isomer
Combustion, pyrolytic cracking, and halogenation are reactions of (alkanes/alkenes/alkynes)
Alkanes
Hydrogenation, Bayer’s test, and ozonolysis are reactions of (alkanes/alkenes/alkynes).
Alkenes
Alkenes are reactive due to the presence of the weaker ________.
Pi bond
Hydrogenation, or the addition of H (reduction) across a double bond, requires one mole of H2 in _____, _____, or _______ for every mole of unsaturation.
Nickel (Ni), palladium (Pd), or platinum (Pt)
Oxidative test used for detection of unsaturation using KMnO4 in base to form MnO2 brown precipitate upon reaction
Bayer’s test
Bayer’s test gives what product
Cis-diol (both unsaturated carbons get -OH on same side)
Reason for Markovnikov addition
Nu (not H) adds to the more stable carbocation, which is the more substituted C
Alkynes are _____ when the triple bond is located at the end or head of the structure, and ____ when it is located internally
Terminal alkyne, internal alkyne
(T/F): alkynes undergo the same reactions as alkenes but require twice the amount of reagent because of the two pi bonds
TRUE.
Ozonolysis of (terminal/internal) alkynes produce carboxylic acid and carbon dioxide versus two carboxylic acids
Terminal
Conjugated aromatic compounds like ______ is the carcinogen found in automobile exhaust and charbroiled food; metabolized in the liver as a reactive epoxide that causes mutation
Benzopyrene
(T/F): Many compounds of benzene are carcinogenic
TRUE.
Replacement of H atom on the aromatic ring by a strong electrophilic species
Electrophilic aromatic substitution
EAS where H is replaced by X using X2, uses what catalyst
Halogenation, FeX2
EAS where H is replaced by NO2 using HNO3, uses what catalyst
Nitration, H2SO4
EAS where H is replaced by SO3H using SO3, uses what catalyst
Sulfonation, H2SO4
EAS where H is replaced by R using RX, uses what catalyst
Friedel-Crafts Alkylation, AlX3
EAS where H is replaced by C=OR using RC=O-X, uses what catalyst
Friedel-Crafts Acylation
In EAS, EDGs (activate/deactivate) the reaction and direct the product to the (meta-/ortho- or para-) position
Activate, ortho- or para-
For alcohols, increase in alkyl chains (increases/decreases) polarity and boiling point
Decreases
Oxidation series of primary alcohol?
Alcohol, carbonyl, carboxylic acid
(T/F): Both secondary and tertiary alcohols are unreactive.
Only tertiary alcohols are unreactive
Acid-catalyzed removal of water from an alcohol to form a substituted or stable alkene
Dehydration
Aldehydes are oxidized to ________, and ketones are oxidized to _______
Carboxylic acid, none
Tollen’s test, which oxidizes aldehydes and not ketones, involves __________ and results in formation of silver mirror.
AgNO3 in NH3
Benedict’s test and Fehling’s test, which oxidize aldehydes and not ketones, involves ______ and _____ respectively and results in the formation of red precipitate (Cu2O)
CuSO4 in NaOH; curpric sulfate in Rochelle salt
Aldehydes are reduced to ________ while ketones are reduced to ________ with the use of NaBH4, LiAlH4, or Gringard Reagent
Primary alcohols, secondary alcohols
Strong acids and strong oxidizing reagents (Bayer’s, Jones or CrO3) oxidize 1º and 2º alcohols to ______ and _____ respectively, while weak oxidizing agents (e.g. Rosemund or PCC) only oxidizes 1º alcohols to ______
Carboxylic acids, ketones; aldehydes
Addition of nucleophilic compound such as alcohol on the carbonyl group
Nucleophilic addition
Nucleophilic addition of aldehydes and ketones gives ________ and _____ with the addition of one molecule of alcohol, while addition of anotehr alcohol yields _____ and _____
Hemiacetal and hemiketal; acetal and ketal
Note: OR from ROH attaches to C, and C=O becomes C-OH
Smaller pKa means (stronger/weaker) acid
Stronger
Condensation of carboxylic acids with alcohol forms an _______ and water
Ester
Condensation of carboxylic acids with amine forms an ______ and water
Amide
Condensation of carboxylic acids with carboxylic acids forms _______ and water
Acid anhydride
Condensation of carboxylic acids with thionyl chloride (SO2Cl) forms _________
Acid chloride
In electrophilic addition, which is added first (electrophile/nucleophile)
Electrophile first, then nucleophile adds to carbocation
Electrophilic addition of alkenes that involves addition of -X and -OH using X2 and H2O in nucleophilic solvent (OH acts as Nu)
Halohydrin formation
Radical addition of HBr to alkenes is possible in the presence of _______.
Peroxides
If the product of the reaction between C2H4 and HBr is treated with aqueous NaOH, you get…
C2H5OH + NaBr
(T/F): Alcohol denatures proteins
TRUE.
