Organic Chemistry

Saponification

Hydrolysis of fat w/ a base such as sodium hydroxide (NaOH). Products: glycerol & soap Fat + NaOH => Glycerol + Soap

What are the first few members of the series?

1st: methanoic acid (aka formic acid). Form: HCOOH. 2nd: ethanol acid (aka acetic acid) 5-6 % aq solution of ethanol acid = vinegar. Form. =CH3COOH.

The members of the alkane series of hydrocarbonds are similar in that each member has the same... 1)empirical formula 2) general formula 3)structural formula 4)molecular formula

2

Natural gas is composed mostly of...

methane

In 2-methylpropane, where is the group, and how many carbons and hydrogens are there?

The group is located on the second carbon of the parent, and has 3 H atoms attached to it, being a methyl. Due to the propane, the parent consists of 3 C atoms, with 10 C in total.

What is the structural formula for diethyl ether?

(from right to left) 1) Top row: . H-H . H-H . Middle Row: H-C-C-O-C-C-H Bottom Row: . H-H . H-H . b/c ethyl = 2, 2 groups w/ 2 C's, ether = w/ O

Organic compounds that are essentially nonpolar and exhibit weak intermolecular forces have 1)low melting points 2)low vapor pressures 3) high conductivities in solution 4) high boiling points

1

Stereoisomers

Isomers whose atoms have diff. arrangements in space

Cracking

A process in which larger hydrocarbon molecules are broken into smaller ones, yielding more important fractions with lower boiling points (ex. gasoline).

Haloalkanes/Halides

Compound where >=1 H atoms in alkane =replaced by corresponding # of halogen atoms. Form.: R-X, X= halogen atom (F, Cl, Br, I). Named by placing the combining form of halogen name (fluoro-, chloro-, bromo-, iodo-) before name of alkane. If needed, prefix (di-, tri- etc.) & #s = assigned to indicate # of halogen atoms present & locations. (ex. 1, 2 - dibromoethane = 2 C's, 4 H's, and 2 Br's.

Alcohols

Contain the hydroxyl function group (-OH). Classifed 1) acc. to # of hydroxyl groups in a molecule 2) acc. to way in which the carbon atoms are arranged within the alcohol molecule. Suffix: -ol to name of parent hydrocarbon.

Carboxyl Group: Organic Acids

A combination of carbonyl & hydroxyl, double bond with O and single w/ OH, usually abbr. as COOH. Confers acidic properties on organic compound. Suffix: -oic + acid after parent hydrocarbon.

Addition reaction

Atoms are "added across" a double or triple bond. As a result, their bond becomes simpler, as in a double bond becomes a single bond. (ex. ethene + Br2 = 1,2-dibromoethane)

What are the prefixes of the alkane series?

1 = meth... 2=eth... 3=prop... 4=but... 5=pent... 6=hex... 7=hept... 8=oct.... 9=non... 10=dec... .. 18-octadec... (all end in -ane)

The functional group (group shown with one C, OO & OH) is always found in an organic.. 1)acid 2)ester 3)ether 4)aldehyde

1)acid (by process of elimination and by definition, b/c ester OO & O, ether = O, aldehyde = C w/ OO & H & R)

Cis vs trans form of stereoisomers

1st stereoisomer = closer methyl groups than in 2nd stereoisomer is the trans form. (put cis- or trans- as prefix before #)

Secondary alcohol

2 C atoms bonded to the OH-containing C atom. Gen. form. = C to OH and one H and R1 or R2. (ex. 2-propanol aka isopropyl alcohol or rubbing alcohol) (being bonded to C can be like C being singly bonded to CH3 2 times)

Dipeptide and How It's Made

2 amino acids in living organisms undergo a condensation reaction where the OH group on 1st molecules & NH2 group on 2nd molecule interact & eliminate H2O, then join to produce this type of amide. Occurs from an amino acids that both have OH, NH2 and a double O bond (OO), creating a dipeptidewith the 2 NH2's, but only one OH, 2 OO's, and the rest. The OH & H from the amino acids that faced each other horizontally become a single bond between C to N in NH2, because the reaction releases a water.

What is the total # of hydroxyl groups contained in 1 molecule of 1,2-ethanediol? 1) 1 2) 2 3) 3 4) 4

2) 2 b/c need 2 OH groups due to 2 #s

Which hydrocarbon has >1 possible structural formula?

C4H10

How should the parent's carbon atoms be numbered if we were to name it?

The carbon atoms of the parent should be numbered in order so that the group is assigned the lowest number possible.

Condensed structural formula

An in-between of the molecular formula and the dashed structural formula, written without dashes. Hydrogen atoms are written to the right of the atom to which they are connected (ex. CH3CH2CH3). If there is a bond that is not completely horizontal, that instead pops out of the molecule, then the condensed structural formula has a vertical line connecting to the C atom that these C and H atoms bond to.

Amino Group

An organic N compound that consists of N bonded to 2 H atoms (NH2).

Functional group

Another element within an organic molecule that's not H or C, classified acc. to manner in which the atoms are arranged in the molecule.

Aldehydes

C of carbonyl group is bonded to >= (at least) 1 H atom. Suffix = -al to parent name. (Ex. methanal, aka formaldehyde: connected to 2 H diagonally, a biological preservative; ethanal: connected to H and CH3).

Which is the gen. form. for ketones?

C w/ OO & R1 & R2

Carbonyl groups

Consists of a C atoms connected to an O atom by a double bond. There are 2 kinds: aldehydes and ketones.

Amide

Derivative of org. acid in which amino group (NH2) replaces OH on carboxyl group: one C, one R, one NH2, and double bond O to C. Named by dropping -oic from name of acid & adding -amide in place. (ex. ethanamide).

Homologous series

Families in which hydrocarbons with related structures and properties are separated into. Each member of this kind of series differs from the the next member by a single carbon atom (alkane, alkyne, alkene).

How are hydrocarbons obtained?

From the refining of petroleum, a complex mixture of natural hydrocarbons.

Benzene series/aromatic hydrocarbons

General form. : CnH2n-6, 1st member: benzene & molecular formula C6H6. It's first and last carbons join together, and because of this it's known as a ring compound.

Esters

General form: C connected w/ double bond to O one direction, then single to an R1, O then R2. Prepared by reaction bet. organic acid & alcohol. Named as derivative of acid & alcohol that formed it. *Name derived from combo of the alkyl group found in alcohol (ethyl) and name of acid, with the suffix -ate, replacing -ic (ex. ethanoic in ethanoic acid to ethanoate). * (ex. ethyl ethanoate: bet. ethanol acid and ethanol, from alkyl in alcohol & name of acid). Usually have nice odor, fruity aromas usually due to esters, determined by type of org. acid and type of alcohol in ester.

Ethers

General form: R1 - O - R2. (ex. ethoxyethane aka diethyl ether: C2H5 - O - C2H5, was a popular surgical anesthetic, may be prepared by dehydrating primary alcohols w/ H2SO4.

Ketone

Has no H atoms directly attached to carbonyl group. Add suffix= -one to parent name. (ex. Propanone: C connected with a double bond to O, and also connected to 2 CH3s, generally attached to R1 and R2, or any carbon group (alkyl). Propanone=acetone as a common name, solvent in nail Polish remover).

How do the melting and boiling points of inorganic and organic compounds compare?

Inorganic compounds have higher melting and boiling points compared to organic compounds (its rare for these to have high ones).

What is the rate of reaction between organic and inorganic compounds?

Inorganic compounds react much more rapidly than organic compounds due to the more simple bond rearrangements in inorganic reactions, which are fewer in number. Organic reactions usually involve functional groups of reactants.

Is there a difference between butane and n-butane?

No. N stands for normal, as in it just consists of the parent line of C atoms.

What are the elements, other than C and H, are most commonly present in organic compounds?

O, N, and the halogens (F, Cl, Br, I).

Addition polymerization

Unsaturated (double/triple bonds) monomers may undergo AP, where the double/triple bonds are reduced to double/single bonds. (ex. n units of thene n(ethene) ==addition==> polyethylene

Dimer

a compound made up of two identical or similar subunits or monomers

protein & enzymes

a molecule that contains 1 or more polypeptide chains. These molecules are huge so when synthesized, they are catalyzed by proteins called enzymes.

In the compound 1,2-dichloroethene, one H atom on each C atom is replaced by a Cl atom. Write the formulas of the 2 stereoisomers of 1,2-dichloroethene.

cis-1,2-dichloroethene ; trans-1,2-dichloroethene

Alcohols (general)

classified as primary, secondary, or tertiary b/c diff. in chemical behavior. Classification based on # of C atoms attached to the C atom that contains the hydroxyl group (OH).

Dihydroxy & trihydroxy alcohols

contain 2 & 2 hydroxyl groups, respectively. Dihydroxy alcohols = glycols (ex. 1,2-ethandiol/ethylene glycol, a component of automobile antifreeze. 1,2,3-propanetriol/glycerol (part of biological processes) = impt trihydyoxy alcohol. (single bonds i think)

Condensation polymerization

monomers= joined by dehydration reaction, in which 2 monomer units condense to form a dimer & H2O. As ^ units are joined to dimer, polymer grows bigger. In order to occur, CP must have at least 2 functional groups that can undergo dehydration (have OH in each!). (synthetic condensation polymers: silicones, nylons, & polyesters.)

Peptide link

the joining of 2 amino acids.

As the number of carbon atoms in the alkane series increases, the masses of the successive molecules increases as well, causing ... because ..

the phase of the substance at STP to change from gas to liquid to solid....the increased strength of London dispersion forces, which occurs in more massive (nonpolar) molecules.

Hydrogenation

Addition of H to an unsaturated compound, used to commercially to solidify liquid vegetable oils.

What is important in observing in order to determine a compound's properties and reactivity?

its structure

Fermentation

A biological process in which oxidation occurs in the absence of oxygen. Enzymes produced by living organisms act as the catalysts for this process. (ex. yeast enzymes will ferment glucose (simple sugar) to produce ethanol and CO2 ---> glucose-> C6H12O6 ==yeast enzymes ==> 2C2H5OH + 2CO2 (ethanol and carbon dioxide) )

Amine

A hydrocarbon in which >= 1 H atoms is replaced by an amino group. Simplest one is aminomethane (C w/ 3 single bonded H and one NH2).

Constitutional isomers

Have the same molecular formula but their atoms are connected in a different order, two or more compounds.

Alkyl groups

Hydrocarbon groups like methyl, ethyl, and propyl, formed when an H atom is removed from an alkane. Referred to generally as R1 - C (triple bond) C-R2 (different subscripts in case the alkyl groups are different.)

Alkenes

Hydrocarbons that contain one C-C double bond. The first member is ethene (C2H2) or more commonly, ethylene. All alkene names end with the suffix -ene. Its general formula ,with n C atoms, is CnH2n.

Alkynes

Hydrocarbons that contain one C-C triple bond. 1st member: ethyne (C2H2), or more commonly, acetylene. All alkyne names end with the suffix -yne. General formula with n carbon atoms: CnH2n-2.

Alkane Series

Hydrocarbons that contain only single bonds between carbon atoms, first member = methane (CH4), a tetrahedral molecule, like every alkane molecule (carbon forms four sp^3 hybrid orbitals). These end with the suffix -ane. Formula= CnH2n+2

What is the procedure for giving an organic compound a name?

If hydrocarbon has no branches & only single-carbon bonds, name acc. to prefixes. 1st: Parent structure=determined, doesn't have to be a straight line; 2nd: modify the name of the parent structure according to the functional groups (alkyls/branches) that are attached to the parent; 3rd: if no groups are attached, parent name=name of hydrocarbon; 4th: when carbon group attached to parent, group=suffix -yl attached to prefix

How are organic compounds' solubility compared to inorganic compounds?

Inorganic compounds are generally soluble in polar solvents, while organic compounds are generally soluble in non-polar solvents. (Why the (organic) oil in a salad dressing does not "mix" w/ vinegar (polar solvent).

Who names the system in which organic compounds are named?

International Union of Pure and Applied Chemistry (IUPAC)

Polymerization

Monomer units = joined to produce polymer (n monomer => (monomer)n ).

Amino acids

Org. acid containing >= 1 amino groups. Simplest: aminoethanoic acid & aminopropanoic acid (aka glycine & alanine). Glycine= 2 C's w/ 2 H's, aN NH2, double bond O, & single bond OH. Alanine: 3 C's, 4 single H's, one NH2, one double bond O, and single OH. Amino acids=building block of proteins & more in living organisms.

Synthetic polymers

Plastic polyethylene (monomer: ethene), nylon, & polyester.

Natural polymer ex.

Proteins (amino acids), cellulose and starch (glucose)

How are the atoms around double carbon bonds held together?

They are held rigidly in position.

Primary alcohol

Zero or one C atom bonded to the hydroxyl-containing C atom. Gen. formula: C connected to OH and R w/ 2 H's.

How does the bonding between inorganic and organic compounds compare?

Inorganic compounds usually bond through ions or polar covalent bonds while organic compounds are usually covalent with little or no polarity.

Neo(insert original organic compound) (ex. neopentane)

It indicates when all but two carbons form a continuous chain.

Formula and structure for propene?

Its molecular formula is C3H6, its structural formula has a double bond of C atoms in the middle, and 3 H atoms diagonally connected to these double bonds, along with a CH3 being diagonally connected. Each C atom has a total of four bonds attached to it.

Fatty acids

Long chain organic acids

What is the simplest hydrocarbon?

Methane (CH4), which is the chief component of natural gas.

What are the three simplest carbon groups that can be attached to parents? (aka simplest alkyls)

Methyl=> CH3 -- ; Ethyl=> CH3CH2-- or C2H5 --; Propyl=> CH3CH2CH2-- or C3H7 --

How many organic compounds are there in comparison to inorganic compounds?

Millions, while inorganic ones are in the tens of thousands

Emulsion

Mixture of 2 or more liquids that =/= mixable

Iso(insert original organic compound name) (ex. isobutane)

This means that this isomer has the same formula as the original organic compound, having all carbons except one form a continuous chain. "Iso" can also indicate that the molecule is an constitutional isomer of another molecule with a common (or trivial) name. (UCLA, http://www.chem.ucla.edu/~harding/IGOC/C/common_name.html)

Which structural formula represents a tertiary alcohol?

Top row: . . . H . . . 2nd Row: . H H-C-H H 3rd row: H-C--C--C-H Last row: . H . OH . H . has an OH w/ 3 R groups/elements on each side

How do organic compound act as electrolytes compared to inorganic compounds?

Unlike organic compounds, inorganic compounds conduct an electric because of ionization or dissociation of the solute.

Dashed structural formula

Uses straight lines to represent chemical bonds (such as the C and H connections for organic comp's). The angles between bonds are usually drawn as either 90 or 180 degrees.

Lipid/Fat

When fatty acids are esterified with glycerol, ester =fat/lipid. Unsaturated/usually liquid if fatty acids contain a large # of double bonds within parent hydrocarbons. (ex. vegetable oils). Animal fats (solid), known as saturated fats b/c parent hydrocarbons = have few double bonds. (*^ double bonds = unsaturated, less double bonds = saturated*)

What raw materials do organic compounds come from?

Petroleum, plant and animal sources

Monomer

Basic unit of a polymer (ex. amino acid for protein, glucose for starch)

Polymer

Large molecule composed of monomers

Which hydrocarbon ought to have the highest normal boiling point? 1)butene 2)ethene 3)pentene 4)propene

3

Tertiary alcohol

3 C atoms bonded to hydroxyl-containing C atom. (gen form. tertiary alcohol C to OH R1 and R2 and R3; ex. 2-methyl-2-propanol) (being bonded to C can be like C being singly bonded to CH3 2 times)

What is the product of the reaction between ethene and clorine? (all drawn) 1) C2H5Cl 2) CH3Cl 3) C2H4Cl2 4)CH2Cl2

3) b/c C2 for "eth" & H4 for "ene" b/c CnH2n + Cl2 b/c Cl is a diatomic molecule

Which equation represents a simple example of cracking? 1) N2 + 3H2 ==600 degrees=>2NH3 2) S + O2 => SO2 3) C3H8 + 5O2 => 3CO2 + 4H2O 4) C14H30 ==60 degrees==> C7H16 + C7H14

4 b/c it needs to break down hydrocarbons. Cracking is another sort of fractional distillation

Esterification & Hydrolysis

Reaction bet. an acid and an alcohol, products: ester (C with double bond O and single bond O) and water . Occurs slowly & must be catalyzed by acids/bases. Ex. of dehydration/condensation reaction. Reaction = reversible and called hydrolysis b/c ester is broken down with water. *Hydrolysis = ester and water => acid and alcohol*

Soap

Salts of fatty acids. Long molecule, nonpolar at one end and ionic at the other. The nonpolar end can form attraction w/ other nonpolar substances (ex. oil) and ionic end can attract polar solvent (ex. water). Soap has the property detergency & can thus bring about emulsion bet. water and oil.

Combustion

Saturated hydrocarbons (aka single bonds) (ex methane) w/ oxygen at high temp. => CO2 & H2O. (CH4 + 2O2 => CO2 + 2H2O) Property =makes alkanes suitable as fuels. W/ limited oxygen, carbon monoxide/carbon (soot) = produced. (2CH4 + 3O2 =>2CO + 4H2O ==> 2CH4 + O2 => C + H2O).

What are the simplest alcohols?

Simplest monohydroxy alcohol contains 1 carbon atom=methanol (or methyl alcohol/wood alcohol), a popular solvent. Formula = CH3OH, one C combined with 3 H, one O, and an H on the other side. Next member in series, ethanol (ethyl alcohol or grain alcohol), contains 2 C atoms. It's used an antiseptic & a component of alcoholic beverages. Formula: CH3CH2OH. 2 connected C atoms, with 5 H, an O, and an H (horizontal).

Isomers

Substances that have the same molecular formula but are different compounds. They differ from one another in their physical and chemical properties.

What is the parent structure and how is it found?

The longest, unbroken chain of C atoms in an organic compound.

What is petroleum used for (as a starting point)?

The production of plastics, textiles, rubber, and detergents.

Hydrocarbons

The simplest organic compounds that only contain C and H.

Organic chemistry

The study of carbon and its compounds

What are the 3 constitutional isomers of butene?

They all have the molecular formula of C4H8. 1-butene has a double C bond with 3 diagonally bonded H atoms, along with a CH2CH3 compound (?) diagonally connected to it. 2-butene has a double C bond with 2 diagonally bonded H atoms (both horizontal) and 2 diagonally bonded CH3 compounds (at the top of the molecule, horizontal) . 2-methylpropene is the 3rd isomer, with 2 diagonal H atoms (one on top of the other, on the left side), and 2 CH3 compounds (on the right side, on top of each other).

Spontaneous organic reactions

When on e type of atom or group is replaced with another type. For ex., halogens (Cl, Br) may be substituted for the H atoms of alkanes, in which one H atom is replaced with a Cl atom from Cl2 and the remaining chlorine atom combines with the substituted H to form HCl. Start: CH4 + Cl2 => HCl + CH3Cl (chloromethane) to CHCl3 + Cl2 => HCl + CC4 (tetrachloromethane)

When is R used?

When one wants to signify the presence of an alkyl group (carbon, H group) w/o ID'ing it specifically.

Fractional distillation

When petroleum is separated into components with different boiling points.

Are individual groups of an organic compound entitled to its own number?

Yes

Polyamide/ polypeptide

a chain containing many amino acid units, a natural polymer