Test 9Organic Chemistry: Review Book Chapter 10, Textbook Chapter 26

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Concepts: 1. Be able to explain what makes carbon such a unique atom and can form so many carbon

compounds.a. Has 4 valence electrons, and therefore can make 4 covalent bondsb. Can share 1, 2, or 3 electrons which can create single, double, or triple bondsc. Can bond with each other or other atoms such as H, O, and Nd. Can link to make rings, chains, plates, or macromolecules

2. Be able to list general characteristics of organic compounds.a. Tetrahedral shape (bond angle at 109∘ ¿b. Non-polar, and therefore insoluble in waterc. Non-electrolyte (do not produce ions and electricity in water)d. Low melting/boiling pointse. Slow reactionsf. Generally combustible

3. Be able to explain why organic compounds are typically non-polar, have low melting/boiling points, and react slowly.

a. They are non-polar because they are symmetrical. Hydrocarbons are generally non-polar, because they have a tetrahedral shape which is considered symmetrical. Even if there is a polar bond, if the geometry of the shape is tetrahedral, the bonding is overall non-polar

b. Non-polar molecules only have the intermolecular force of dispersion (very weak). So since the intermolecular force is weak, when melting/boiling, it is easy to break the molecule apart, and thus, the melting/boiling point is low.

c. Organic compounds have a high activation energy. Since the activation energy is high, it is difficult to start the chemical reaction, and therefore it reacts slowly.

4. Be able to identify a saturated or unsaturated hydrocarbon.a. Saturated hydrocarbon - hydrocarbon with only single bondsb. Unsaturated hydrocarbon - hydrocarbon with double or triple bonds

5. Be able to draw structural formulas for all types of organic molecules if given a name.a. Alkane

Pentanei. Remove “ane” (pent)

ii. Find, in table P, the number of carbons that corresponds with the prefix (5)iii. Draw out that number (5) carbons in a chain with single bonds, and then

surround them with hydrogens

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b. Branched alkanes3 - ethyl hexane

i. Draw out the longest carbon chain (6 carbons because of the prefix “hex”)ii. Use the number given (3) to find the place to draw the branch

iii. On that number (3) draw a branch using the carbon number of the first word (2, because of “ethyl”)

c. Alkenei. See regular alkanes, but put a number to represent where a double bond is

d. Alkynei. See above, but with a triple bond (butene would become butyne)

e. Halide1 - bromobutane

i. Draw out the alkane chain (butane, so 4 carbons)ii. Take the number given (1) with the element (bromine), and put the element on

that number carbon

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f. Alcohol4 - octanol

i. Draw out the carbon chain (oct-, so 8)ii. Take the number given (4) and bond an OH to that carbon

g. EtherButyl Hexyl Ether

i. Write out the two carbon chains (but-, so one of 4; hex-, so one of 6)ii. Connect the chains with an “o”

h. AldehydeHeptanal

i. Draw the carbon chain (hept-, so 7)ii. Double bond an O to the first carbon (either to the right or to the left)

i. Ketone5 - decanone

i. Draw out the longest carbon chain (deca-, so 10)ii. Use the number (5) and double bond an O to that number carbon

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j. Organic AcidOctanoic Acid

i. Draw out the longest carbon chain (octa-, so 8)ii. Double bond an O and an OH to the first carbon

k. EstersPropyl Pentanoal

i. Draw out the two carbon chains (prop-, so 3; pent-, so 5)ii. In the middle, single bond one O and double bond another O to the last carbon

in the first chain

l. Amines3 - octanamine

i. Draw out the longest carbon chain (oct-, so 8)ii. Use the number (3) and bond an NH2 to that number carbon

m. AmidesPentanamide

i. Draw out the longest carbon chain (pent-, so 5)ii. Double bond an O and single bond a NH2 to the first carbon

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6. Be able to name all types of organic molecules when given the structural formula.a. Alkane

i. Count the longest chain of hydrocarbons (3)ii. Find the prefix from table P that represents that number of carbons (prop-)

iii. Add “ane” (propane)b. Branched alkanes

i. Find the longest chain, and name it (like a usual propane)ii. Locate the branch that is off of the longest chain. Go by the carbon number (ex:

if the branch begins at the second carbon, you would write a 2)iii. Name the chain (if there is one carbon in the chain, it would be methyl)iv. Put it all together (2 - methyl propane)

c. Alkened. Alkynee. Halidef. Alcoholg. Etherh. Aldehydei. Ketonej. Organic Acidk. Esters

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l. Aminesm. Amides

7. Be able to write molecular & condensed formulas for all types of organic molecules.a. Molecular: states the number and kind of atoms in a molecule

i. Ex: propane is C3H8 (see picture in #6 above representing 3 carbons and 8 hydrogens)

b. Condensed: abbreviated structural formulai. Ex: propane is CH3CH2CH3 (see structural picture above in #6)

8. Be able to identify & draw isomers.a. Isomers are compounds that have the same molecular formulas but different structuresb. Example:

2 - methylpentane 3 - methylpentane

9. Be able to identify members of homologous series ( alkanes, alkenes, and alkynes ).a. Alkanes - single bondsb. Alkenes - double bondsc. Alkynes - triple bonds

10. Be able to explain why alkanes can vary in phase. ( solid, liquids, and gases )a. Alkanes have low melting/boiling points, so as the mass increases, the IMF also

increases11. Be able to differentiate between an alcohol and a base.

Bases Alcohols

● Form OH- ions in water● Lack carbon● Fall apart

● Do not form OH- ions in water● Have carbon● Keep together

12. Be able to differentiate between an organic acid and an inorganic acida. An organic acid has carbon, whereas an inorganic acid does not

13. Be able to identify types of organic reactionsa. Substitution

i. Reactant is a saturated (single bond) hydrocarbonii. Two products to begin with, two products are produced

iii. In the two beginning products, one “swaps” with the other to produce a mix of both products at the end

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b. Additioni. Double/triple bond (unsaturated) is opened

ii. Two products to begin with, one product is producediii. The hydrocarbon bond breaks and allows for the two other atoms to be placed

next to each other in the new hydrocarbon

c. Fermentationi. Sugar with the help of yeast makes alcohol and carbon dioxide

d. Esterificationi. Organic acid and alcohol produce an ester and water

ii. Use dehydration synthesis - remove H2O to combine - remove an H from one molecule, and an OH from another

e. Saponificationi. Used to make soap

ii. Fat and NaOH makes soap and glycerol

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f. Combustioni. Makes heat

g. Polymerizationi. Monomers link to make one big polymer

ii. Addition polymerization1. Small molecules with double bonds open one of their bonds and link

together

iii. Condensation polymerization (dehydration synthesis)1. Remove an H2O to link the chains together

h. Fractional Distillation

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i. Separates components by difference in boiling points - lower boiling point boils off first

1. Smaller hydrocarbons have lower boiling points and condense higher up distillation column

ii. Cracking - breaking large molecules into smaller molecules. We break apart the heavy hydrocarbons into smaller hydrocarbons.

i. Amino Acidsi. Amino acids is an anime plus an organic acid

ii. Proteins - lots of amino acids linked together14. Be able to complete organic reactions, if a product or reactant is missing.15. Be able to give examples of synthesized and natural polymers.

a. Synthesized: plastici. Polyester

ii. Polytheneiii. Vinyliv. Plasticv. Gum

b. Natural: i. Silk

ii. Wooliii. Cottoniv. Proteinsv. DNA

16. Be able to explain fractional distillation.a. Crude oil arrives in barrels (crude oil is full of hydrocarbons). The oil is fed into a boiler

and then a distillation column. The hydrocarbons with the lowest mass, the fewest number of carbons, rise first and the highest. There, they are collected and separated. The same thing happens again and again as you go down with different hydrocarbons with different masses.

17. Be able to explain why alcohols have a higher boiling point than similar hydrocarbons.

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a. Alcohol can have hydrogen dipole-dipole forces in addition to dispersion forces, which are relatively strong forces, whereas similar hydrocarbons only have dispersion forces, which is weak. Stronger forces are harder to boil, and therefore alcohols have higher boiling points than similar hydrocarbons.

18. Be able to explain why an alcohol is soluble but the corresponding alkane is not.a. Alkanes are non-polar, whereas alcohols are polar. Since “like dissolves like,” the polar

water can dissolve the “like” polar alcohol

VOCABULARY● Organic Chemistry - the study of structure, properties, and reactions containing carbon● Functional Group - an atom or group of atoms that contains the type of organic

compound● Substitution Reaction - reaction when a hydrogen is replaced by a halogen● Cracking - break of large molecules into many smaller molecules● Saturated - an organic compound that contains only single bonds● Unsaturated - an organic compound that contains double or triple bonds● Halide - hydrocarbon with one or more halogens attached● Addition Reaction - when double or triple bonds between carbons are opened and two

atoms are inserted with new bonds next to each other● Protein - chain of amino acids● Alcohol - a hydrocarbon with the functional group “OH” attached● Hydrogenation - the process of adding H2

● Amino Acid - an anime plus an organic acid● Hydrocarbon - a molecule that only contains atoms of hydrogen and carbon● Ether - molecule with an oxygen bridge between two hydrocarbons

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● Halogenation - addition of a halogen● Tetrahedral - a pyramidal like structure with 4 points● Aldehyde - a hydrocarbon with an oxygen double bonded to the first carbon in the chain● Fermentation - production of ethanol (C2H5OH) from a sugar● Activation Energy - energy needed to start a chemical reaction● Ketone - a hydrocarbon that has an oxygen double bonded to a carbon somewhere

along the chain● Dehydration Synthesis - the process of combining two molecules by removing water,

H20 (remove H from one molecule and OH from the other)● Combustible - flammable● Organic acid - a hydrocarbon where both an oxygen and an OH are double bonded to

the first carbon● Esterification - the process of creating an ester through dehydration synthesis (see

above)● Electrolyte/non-electrolyte - ● Ester - a hydrocarbon that has an oxygen single bonded as well as an oxygen double

bonded to the same carbon atom in a chain● Saponification - production of soap and glycerol from a fat and an NaOH molecule● Alkane - hydrocarbons that contain single bonds● Amines - hydrocarbon that has a NH2 atom bonded somewhere in the chain● Glycerol - a trihydroxi molecule C3H5(OH)3

● Molecular Formula - indicates the number and types of atoms in a molecule (ex: C3H8)● Amides - a hydrocarbon that has an oxygen atom double bonded to the first carbon, as

well as an NH2 also bonded to the first carbon● Combustion - burning reaction with O2 and H2O as products● Structural Formula - demonstrates the shape of molecules and how they are bonded● Polymerization - linking monomers to make a polymer● Condensed Formula - abbreviated structural formula (exL CH3CH2CH3)● Polymer - a big chain link of monomers● Homologous Series - a family of organic compounds where each member has similar

structures and the same general properties● Monomer - small molecules● Isomer - compounds that have the same molecular formula but different structures● Addition Polymerization - small molecules containing double bonds link together by

opening one of their double bonds● Alkene - hydrocarbon with a double bond● Condensation Polymerization - polymerization through dehydration synthesis● Alkyne - hydrocarbon with a triple bond

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● Fractional Distillation - the process of separating components by difference in boiling points

● Petroleum - crude oil that found in the earth, composed of a mix of hydrocarbons

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