Organic.chap11.17
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| Organic chemistry | Study of carbon compounds (not just living cells)
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| Characteristics of organic compounds | a.) Nonpolar-attractions between molecules are weak 2. Low boiling & melting points 3. High flammability 4.Most or not soluble in water unless a polar group is present
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| Hydrocarbons | Organic compounds that contain ONLY hydrogen and carbon
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| In organic compounds, every carbon atom ALWAYS has four bonds - true or false? | TRUE
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| Tetrahedral structure of carbon | Can be drawn as ball-and-stick model, etc.
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| Alkanes | Class or family of organic compounds that a.) contain only carbon and hydrogen atoms and b.) ONLY form single bonds
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| Alkanes (examples) | Many are fuels - methane, ethane, propane and butane
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| Alkanes (structure) | Contain two, three, four, etc. carbon atoms connected in a CONTINUOUS CHAIN
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| Pent | 5
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| Hex | 6
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| Hept | 7
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| Oct | 8
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| non | 9
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| dec | 10
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| Condensed structural formula | write each carbon atom & its attached hydrogen atom as a group
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| Alkyl group | A carbon branch - an alkane that is missing on hydrogen atom
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| Can Alkyl groups exist on their own? | No, they must be attached to a carbon chain
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| A halogen atom attached to a carbon chain | a HALO group - Remember the halogen group?
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| Halogen group molecules: | Fluoro (F), Chloro (CL), Bromo (Br), and Iodo (I)
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| Substituent | 1.) alkane with four or more carbon atoms, 2. atoms can be arranged so that a side or BRANCH or SUBSTITUENT
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| Isomer | Two compounds - SAME molecular formula but different ARRANGEMENTS of atoms
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| Haloalkane | Halogen atoms (flourine, bromine, chlorine, iodine) instead of hydrogen (alkyl group) these are halo-alkanes
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| alkanes | gasoline, diesel fuels, heating oil, mineral oil, petrolatum
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| Alkanes - solubility and density | nonpolar (insoluble in water) BUT they are soluble with other nonpolar solutes (other alkanes) - Less dense than water (they float)
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| First 4 alkanes | methane, ethane, propane and butane-are gases at room temperature - used as heating fuels
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| Alkanes have 5-8 carbon atoms | Pentane, hexane, heptane & octane - are liquids at room temperature, volatile
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| Alkanes with 9-17 carbon atoms | Kerosene, diesel, & jet fuels -higher boiling points - higher molecular weights
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| Alaknes with 18 or more carbon atoms | Waxy solids at room temperature-paraffins - coat fruit - petrolatum or Vasline, is a mixture of liquid hydrocarbons
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| Alkanes - melting and boiling | Lowest melting & boiling of all organic compounds
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| Carbon-carbon bonds - combustion | Carbon-carbon single bonds are difficult to break-alkanes are the LEAST reactive family BUT they burn readily in oxygen
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| Combustion | Alkane + O2 ------ CO2 + H2) + energy
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| In alkanes, how are carbon atoms classified? | Primary-1 degree - carbon is bonded to another carbon - Secondary - 2 degree--carbon has two carbon atoms attached to it - Tertiary - 3rd degree carbon-bonded to three other carbons
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| halogenation of Alkanes (substitution) | Atoms of a halogen (fluorine, bromine, chlorine, iodine) replace hydrogen atoms - when exposed to light or heated
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| Chlorination | When the process of HALOGENATION (replacing a hydrogen atom with a halogen-group atom) uses chlorine
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| Bromination | When halogenation uses bromine
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| Halogenation - compare to hydrogen bonding | Halogens have 7 valence electrons; therefore they form one bond
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| Functional groups | compounds react in predictable ways
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| Alkenes | Functional group - contains a double bond between two adjacent carbon atoms
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| Alkynes | Contain a triple bond between two adjacent carbon atoms
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| Aromatic compounds | Contain Benzene - a molecule with a ring of six carbon atoms with one hydrogen atom attached to each carbon atom
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| Aromatic compounds | Benzene ring
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| Alcohol | Have a hydroxyl group (-----OH) Oxygen plus carbon equals alcohol!
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| Ethers | Functional group - one oxygen atom bonded to two carbon atoms
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| Aldehydes & ketones | Contain carbonyl group C===O (Carbon double-bonded to oxygen
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| Aldehyde | Caron atom of the carbonyl group is bonded to one carbon & one hydrogen atom
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| Ketone | Carbonyl group is bonded to two other carbon atoms
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| Amines | Central atom is nitrogen atom
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| Amines | Derivatives of ammonia NH3 - carbon atoms replace one, two or three of the hydrogen atoms
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| AmiDDDDe | Instead of hydroxyl group as in carboxylic acid -- there is a nitrogen group
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| shape of carbon atoms | tetrahedral
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| combustion - alkanes | Alkane + O2 ---CO2 + H2O + energy
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| Alcohols | A class of organic compounds that contains the hydroxyl (--OH) group bonded to a carbon atom
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| Aldehydes | A class of organic compounds that contains a carbonyl group (C==O) bonded to a least one hydrogen atom
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| Alkanes | Hydrocarbons containing only single bonds between carbon atoms
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| Alkenes | Hydrocabons that contain carbon-carbon double bonds (C==C) Hint: Alkenes contains two "e" and they contain two "C" bonds
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| What is the degree of angle for the carbon tetrahedron? | 109.5
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| Cycloalkanes | Carbon atoms form a ring or cyclic structure
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| How do you write name of cycloalkane? | prefix "cyclo" before the alkane name with the same number of carbon atoms
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| What does the IUPAC name indicate in organic molecules? | It indicates the NUMBER of carbon atoms
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| A continuous alkane | Carbon atoms are connected on a chain and bonded to hydrogen atomes
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| Sustituents can replace __________ on an alkane | Sustituents replace hydrogen atoms
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| A Haloalkane contains one or more | F, CL, Br or I atoms
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| condensed structural formula | Show arrangement of carbon atom in a molecule but group each carbon with its bonded hydrogen atom
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| halogenation reaction | A substitution reaction - can occur naturally in light or with heat - halogen atoms replace hydrogen atoms in an alkane
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| line-bond formula | A type of structural formula that shows only the bonds from carbon to carbon
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| Are organic compounds typically solid at room temperature? | No, that is more characteristic of inorganic compounds, which also have high melting & boiling points, are soluble & have strong covalent bonds
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| polymers of alkanes - what are they? How do they occur naturally? | Long-chain molecules that consist of many repeating units of smaller carbon molecules (monomers) Cellulose & starch are polymers of glucose
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| Name two polymers of glucose | Cellulose & starch
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| Name two polymers of amino acids | Proteins are polymers of amino acids
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| Synthetic polymers - Ex. | nonstick Teflon -poly tetra flouro ethylene
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| Aromatic compounds-what is the base? | Benzene "rings" smells
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| Benzene | A ring of 6 carbon atoms with one hydrogen atom attached to each carbon
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| Naming aromatic compounds | ortho (1,2 arrangement) - meta (m) 1,3 arrangement and para (p) is 1,4 arrangement
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| Ortho - di chloro benzene | 1,2 chloro on benzene ring
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| Ortho | "o-o's" don't go very far from each other 1-2 are not far from each other
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| Meta (m) | Meta (m) 1,3 arrangment - "a-e" are three steps apart
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| Para (p) | 1,4 (ara) first are separate by a number from the back of the alphabet
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| sulfanation | "Sulfa saved our nation" sulfa drugs produced by adding sulfur to benzene rings
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| Nitration | Benzene is heated with nitric acid
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| Halogenation | (blank)
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| Markovnikov's rule | (blank)
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| halogenation adds _____ or ______ to form _______ | Halogenation adds Cl2 or Br2 to form haloalkane
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| Hydorhalogenation adds ______ and _______ to form ________ | Hydrohalogenation adds HCl, HBr to form haloalkanes
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| Hydrogenation adds ______ to form _____ | Hydrogenation adds H2 to form Lakanes
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| Hydration adds ______ to form ______ | Hydration adds H2O to form alcohols
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| Aromatic compounds undergo _________ reactions, because they are stable | Aromatic compounds undergo SUBSTITUTION reactions such as halogenation, nitration and sulfonation
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| Unsaturated hydrocarbons | A compound of carbon & hydrogen which contains at least one double or triple bond
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| Cis isomer | A geometric isomer which simlar gropus are connected on the same side of the double bond
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| Trans isomer | A geometric isomer in which similar gropus are connected to opposite sides of the double bond in an alkene
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| Alcohol | A hydroxyl group (--OH) replaces a hydrogen atom in an alkane
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| What makes alcohol in Ohio? | An --OH group bonded to a carbon atom OR A CARBON CHAIN
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| Chain-chain-chain of fools... | When naming alcohols, count longest chain CONTAINING the --OH group
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| Phenol | benzene ring with --OH group
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| ethanol | ethyl alcohol - intoxicating product - ethene plus water used to make commercial alcohols such as varnishes
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| Phenal is part of essential oil of plants | such as eugenol (in cloves0
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| Why is glycerin good in soaps? | it is a trhydroxy alcohol - the presence of polar --OH groups makes it strongly attracted to water, so that it is useful as a skin softener
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| Thiols | SMell bad - if you had to smell someone thigh - all over -- you'd stink - oysters, cheddar chees
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| What is on the thiols? | an --SH group
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| Ethers | Have OXYGEN atom attached by SINGLE BONDS - to two carbon groups
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| ether (structure) | "Either or" the oxygen is in the middler, the carbon is either on one side or the other,
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| ether (examples) | ethers are anesthetics - inhibit pain signals to the brain
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| Cyclic ethers (example) | Dioxin-formed during forest fires - is highly toxic
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| Cyclic ethers | have an oxygen atom within a carbon ring Di-oxin
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| Alcohol | --OH group replaces a hydrogen atom
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| Phenol | Hydroxyl --OH group is attached to aromatic rings
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| Thiols | family of organic compounds containing sulfhydryl --SH group (similar to alcohol but --SH group takes the place of an --OH group
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| Who wants to smell my thigh--all? | YECCH--skunks, onions, and garlic have THIOL
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| Primary alcohol | One alkyl group (CH3) attched to carbon atom
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| Secondary alcohol | 2 degrees - has two Alkyl (CH3) group attached
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| Tertiary 3 degree | Has three alkyl (CH3) groupps attached to it
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| Phenols | Benzene ring bonded to hydroxyl --OH group
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| Phenol - Beano-drunko | benzene (beano) with hydroxyl group
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| T | (blank)
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| ester | H in carboxyl group is replaced with an alkyl group
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| Esterification | Carboxylic acid and alcohol react (in presence of acid catalyst) to produce an ester
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| Ester (examples) | Aspirin, oil of wintergreen
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| esters - fruits & flowers | give them their fragrance
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| lipids | biomolecules that contain fatty acids or steroid nucleus
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| what type of lipid does NOT contain fatty acids? | steroids
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| Fatty acid formulas | Long line-bond formulas (remember video of guy holding long model)
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| Do fatty acids contain carboxylic acids? | Yes --they are composed of
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| Fatty acid formulas (condensed) | Indicate # of carbon atoms, # of double bonds & the position of the double bonds
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| Saturated fatty acids (naturally occuring) | SINGLE C-C bonds; fit closely together, strong attraction between fatty acid chains MEATS
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| UNsaturated fatty acids | Kinky, loose--liquid-low melting point
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| Prostaglandins - weird name, weird shape | trans double bond on carbon 13 - look like long "U's"
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| Fatty ACID** | a long carbon chain with CARBOXYLIC ACID group at one en
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| Prostaglandins- what number is so associated with them that they are sometimes called ____ | 20 - they have 20 carbons - called "eicos" - greek word for 20
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| What is structure of most prostoglandins? | hydroxyl group on cabron 11&15 - trans double bond on carbon 13
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| What do prostaglandins do? | increase blood pressure, cause pain & inflammation in injured tissue
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| Esters | fatty acid plus long-chain alcohol
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| Triacylglycerols | Fatty acids stored in body
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| How are triacylglycerols formed? | "tri" three acyl (the fatty acid?) plus glycerol (
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| hydrogenation | ADDITION REACTION - Unsaturated fats with Carbon-carbon double bonds to single bonds
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| traicylglycerols - how are they formed? | through esterification - hydroxyl groups ract with carboxyl groups of fatty acids
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| Glycerophospholipid - Structure (think LAB-stuff floating in water) | POLAR head (amino alcohol) with NONPOLAR fatty acid chains -
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| Glycerophospholipid - examples (think brainy - the word is so long you have to be brainy to find it) | Lecithin - in brain & nerve tissues - egg yolks, wheat germ & yeast
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| SPHINGOLIPIDS | found in nerve cells
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| sphingolipids | "SPHinx" has a big head - nerves are in your head
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| sphingomyelin | white matter of myelin sheath--surrounding nerve cells
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| glycosphingolipids & cerebroside | sphingolipids that have sugars (glyco--stupid)
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| gangliosides | "GANG UP - tay-sachs disease-accumulates in body
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| steriod | "steering wheels" - FOUR rings - 3 cyclohexane plus 1 cyclopentane
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| Do steroids contain fatty acids? | NO - and they're non-polar
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