Chemistry: Organic Chemistry Flashcards by A R

Aromatic character is denoted by ________.

Having conjugated pi bonds in resonance, allowing for more stability

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A compound that contains an EDG in the ring is (more/less) aromatic than a compound that contains an EWG (EN).

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______ 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

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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

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If a compound rapidly decolorizes in a solution of bromine in an inert solvent, the compound is _______.

Unsaturated

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Ozonolysis, which uses O3 to uncleave unsaturated compounds, replaces unsaturated bonds with __________.

Double bonds with oxygen

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Grignard reagent is (nucleophilic/electrophilic) and when added to CO2, _______ is formed after acidification.

Nucleophilic, carboxylic acid

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Process involving conversion of fat, oil, or lipid into soap and alcohol by action of aqueous alkali

Saponification

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Chemical process by which an alkyl group is attached to an organic substrate molecule via addition or substitution

Alkylation

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Process of combining an organic acid (RCOOH) with an alcohol (ROH) to form an ester (RCOOR) and water

Esterification

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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

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Ratio of the equilibrium concentrations of products over the equilibrium concentrations of reactants each raised to the power of their stoichiometric coefficients

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If all coefficients of the equilibrium equation are divided by 2, the Kc is decreased by what factor

By square root of the Kc

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Seven metalloids

Boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), tellurium (Te), and polonium (Po)

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(T/F): An element melts at a definite temperature.

TRUE.

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(Metals/metalloids/nonmetals) have high MP, good conductors of elec/heat, high density, malleable, ductile, solid at room temp

Metals

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Oxides that combine with metals form _____ whereas oxides that combine with nonmetals form _____. (Acids/bases)

Bases, acids

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Only metal which is liquid at room temperature

Mercury

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(T/F): All metals are hard.

FALSE.

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(T/F): All metals can combine with oxygen easily.

FALSE.

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(T/F): All metals are good conductors of heat and electricity.

TRUE.

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Scattering of a beam of light by a medium containing small suspended particles

Tyndall effect

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Higher vapor pressure (higher/lower) the amount of pressure exerted on the liquid by the atmosphere, resulting in (higher/lower) boiling point.

Lowers, lower

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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

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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.

(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.

Chemistry: Organic Chemistry Flashcards

(102 cards)