Organic Chemistry Test 1

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the study of compounds that contain the element carbon.
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organic chemistry
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natural organic compounds
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cotton, wool, or silk
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synthetic organic compounds
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nylon and polyester
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what do all organic compounds contain?
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carbon and hydrogen atoms
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carbon always forms how many covalent bonds?
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4
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what type of bonds can carbon form?
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single, double, or triple
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a carbon atom surrounded by four atoms four single bonds
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ethane
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a carbon atom surrounded by three atoms forms one double bond
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ethylene
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a carbon atom surrounded by two atoms generally forms one triple bond
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acetylene
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what are two types of compounds?
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ring or chain
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any atom that is not carbon or hydrogen
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heteroatom
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what are the most common heteroatom?
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halogens
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what is the most common multiple bond between carbon and a heteroatom?
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carbon-oxygen double bond
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an atom surrounded by two groups
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linear
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what angle does linear have?
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180
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an atom surrounded by three groups
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trigonal planar
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what is the angle of trigonal planar
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120
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an atom surrounded by four groups places these four groups at the corners of a tetrahedron
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tetrahedral carbon
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what is the angle of tetrahedral carbon?
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109.5
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used to show bonds in the plane
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solid line
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used to show bonds in front of the plan
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wedge
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used to show bonds behind the plan
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dashed line
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all carbons having four single bonds are what?
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tetrahedral
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what molecular shape has three bonds and one lone pair?
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trigonal pyramid
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what molecular shape has two bonds and two lone pairs?
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bent
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what are two shorthands for representation of organic compounds?
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condensed and skeletal
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what are the rules for condensed structures?
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1. all of the atoms are drawn in, but the two-electron bond lines are generally omitted. 2. lone pairs on heteroatoms are omitted.
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a carbon bonded to 3 h’s
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CH3
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a carbon bonded to 2 h’s
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CH2
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a carbon bonded to 1 h
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CH
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what are the rules for skeletal structures
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1. assume there is a carbon atom at the junction of any two lines or at the end of any line. 2. assume there are enough hydrogens around each carbon to give it four bonds. 3. draw in all heteroatoms and the hydrogens directly bonded to them.
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an atom or a group of atoms with characteristic chemical and physical properties
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functional group
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contains a heteroatom, a multiple bond, or sometimes both a heteroatom and a multiple bond.
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functional group
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what does a functional group determine?
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the molecule’s shape, properties, and the type of reactions it undergoes
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a compound with a functional group with OH
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hydroxyl group
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hydroxyl groups are called what?
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alcohols
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what are the three most common functional groups?
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1. hydrocarbons 2. compounds containing a single bond to a heteroatom 3. compounds containing a C=O group
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compounds that contain only the elements of carbon and hydroge
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hydrocarbons
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only C-C single bonds and no functional group.
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alkanes
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C-C double bond as their functional group
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alkenes
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C-C triple bond as their functional group
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alkynes
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contain a benzene ring, a six membered ring with three double bonds
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aromatic compounds
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compounds contain a carbon-oxygen double bond
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carbonyl group
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what do carbonyl groups include
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1. aldehydes 2. ketones 3. carboxylic acids 4. esters 5. amides
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R-X
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alkyl halide
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R-OH
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alcohol
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R-O-R
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ether
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R-NH2
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Amine
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oxygen double bonded to carbon which is bonded to an R and an H
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aldehyde
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oxygen double bonded to a carbon bonded to two R
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ketone
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oxygen double bonded to a carbon boned to a R and OH
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carboxylic acid
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oxygen double boned to a carbon boned to a R and OR
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ester
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oxygen double bonded to a carbon bonded to a R and N that is bonded to two Hydrogen
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amide
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has a hydrogen atom bonded directly to the carbonyl carbon
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aldehyde
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contains an OH group bonded directly to the carbonyl carbon
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carboxylic acid
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contains OR group bonded directly to the carbonyl carbon
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ester
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do organic compounds have high or low melting and boiling points?
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low
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what does the polarity of an individual bond depend on?
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the electronegativity of the atoms that form it
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when is a covalent bond non polar?
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when two atoms of identical or similar electronegativity are joined together
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when is a covalent bond polar?
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when atoms of different electronegativity are joined together.
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are bonds between carbon and common heteratoms polar or nonpolar
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polar
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what symbol is given to the less electronegative atom
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the positive one
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what symbol is given to the more electronegative atom
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the negative one
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are organic compounds soluble in water?
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no
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what are organic compounds soluble in?
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organic solvents
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are hydrocarbons polar or nonpolar
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nonpolar
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what determines the shape of the molecule?
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the overall polarity
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if the individual bond dipoles cancel in a molecule what is the molecule?
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nonpolar
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if the individual bond dipoles do not cancel the molecule is what?
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polar
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are hydrocarbons and other non polar organic compounds soluble in water?
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no
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when are polar organic compounds soluble in water?
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if they are small and contain a nitrogen or oxygen atom that can hydrogen bond with water.
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what reaction does alkanes undergo?
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combustion
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alkanes that contain chains of carbon atoms but no rings are called what?
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acyclic alkanes
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what is the molecular formula for acyclic alkane
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CnH2n
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contain carbons joined in one or more rings
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cycloalkanes
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the formula for cycloalkane
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CnH2n
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has a single carbon atom surrounded by four hydrogens to give it four bonds
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methane
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has two carbon atoms joined together by a single bond.
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ethane
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has four carbon atoms in a row
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butane
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has three carbon atoms in a row and one carbon bonded in the middle carbon
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isobutane
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two different compounds with the same molecular formula
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isomers
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the same family of compounds differ in the way the atoms are connected to each other
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constitutional isomers
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one carbon
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methane
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two carbons
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ethane
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three carbons
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propane
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four carbons
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butane
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five carbons
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pentane
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six carbons
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hexane
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seven carbons
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heptane
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eight carbons
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octane
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nine carbons
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nonane
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ten carbons
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decane
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carbon atoms in alkanes and other organic compounds are classified by what?
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the number of other carbons directly bonded to it
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bonded to one other C
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primary carbon
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bonded to two other carbons
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secondary carbon
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binded to three other carbons
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tertiary carbon
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bonded to four other carbons
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quaternary carbon
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the systematic name follows the accepted rules of nomenclature; this is the IUPAC name
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systematic
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the generic name is the official, internationally approved name for the drug
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generic
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the trade name for a drug is assigned by the company that manufactures it
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trade
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alkanes that have carbon branches
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substituents
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indicates the number of carbons in the longest continuous carbon chain in the molecule
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parent chain
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indicates what functional group is present
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suffix
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tells us the identity, location, and number of substituents attached to the carbon chain
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prefix
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what does the suffix -ane indicate?
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it is an alkane
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the parent name for one carbon
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meth
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the parent name for two carbons
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eth
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carbon substituents bonded to a long carbon chain
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alkyl groups
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formed by removing one hydrogen from an alkane
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alkyl group
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how do you name an alkyl group
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change the ane to yl
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1 carbon in an alkyl group
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methyl
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2 carbon in an alkyl group
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ethyl
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3 carbon in an alkyl group
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propyl
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4 carbon in an alkyl group
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butyl
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5 carbon in an alkyl group
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pentyl
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6 carbon in an alkyl group
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hexyl
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contain carbon atoms arranged in a ring
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cycloalkanes
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do alkanes have strong or weak intermolecular forces?
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weak
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what does oxidation result in?
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an increase in the number of C-O bonds or a decrease in the number of C-H bonds
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what does reduction result in?
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a decrease in the number of C-O bonds or an increase in the number of C-H bonds
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acyclic alkane formula
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CnH2n+2
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alkyne molecular formula
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CnH2n-2
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what type of hydrocarbons are alkenes and alkynes
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unsaturated hydrocarbons
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suffix of alkene
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ene
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suffix of alkyne
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yne
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when the two CH3 groups are on the same side of the double bond
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cis isomer
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when the two CH3 groups are on opposite sides of the double bond
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trans isomer
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are cis and trans compounds constitutional isomers?
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no
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isomers that differ only in the 3-d arrangement of atoms
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steroisomers
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alkenes undergo what type of reaction?
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addition reaction
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what is added in addition reactions?
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a new X and Y group
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what happens in an addition reaction?
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the weak bond is broken and two new strong single bonds are formed
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the addition of hydrogen(2) to an alkene
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hydrogenation
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in hydrogenation, the addition of the two hydrogen occurs when?
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when a metal catalyst is in presence
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what does hydrogenation form?
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alkane
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the addition of halogen (x2) to an alkene
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halogenation
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two bonds are broken– one bond of the carbon-carbon double bond and the X-X bond– and two nee C-X bonds are formed
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halogenation
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the addition of HX
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hydrohalogenation
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one bond of the carbon-carbon double bond and the H-X bond form what?
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C-H and C-X bonds
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the product of halogenation
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dihalide
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the product of hydrogenation
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alkyl halide
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the addition of water
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hydration
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one bond of the carbon-carbon double bond and the H-OH bond and the new C-H and C-OH bonds are formed in what
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hydration
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how can hydration occur
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if a strong acid like H2SO4 is used as a catalyst
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what is the product of hydration
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alcohol
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the most stable arrangement keeps the groups on a central atom as far away from each other as possible
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VSEPR
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what is a carbonyl group?
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a carbon-oxygen double bond
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carbonyl group compounds
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aldehyde, ketone, carboxylic acid, ester, amide
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the molecular formula for cycloalkanes
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CnH2n
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contains 1 or more carbon bonded to 3 or more C atoms
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branched-chain
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has all of its carbons in one continuous chain
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straight-chain
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substituent F
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fluoro
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substituent Cl
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chloro
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substituent Br
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bromo
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substituent I
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iodo
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alkenes are what at room temperature
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gases
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larger alkenes are what substance in room temperature
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liquids
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the higher amount of carbon atoms the higher what?
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boiling point
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molecules with the same molecular formula but different 3D
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configuration isomers
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same molecular formula, same connectivity, but different 3-D arrangement
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steroisomers

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