| Question |
Answer |
| WHAT IS AN ISOMER | DIFFERENT COMPOUNDS THAT HAVE THE SAME MOLECULAR FORMULA |
| WHAT IS A CONSTITUTIONAL ISOMER | DIFF. COMPOUNDS THAT HAVE THE SAME MOLECULAR FORMULA BUT DIFFER IN THEIR CONNECTIVITY |
| WHAT IS AN IONIC BOND | THE TRANSFER OF ONE OR MORE ELECTRONS FROM ONE ATOM TO ANOTHER TO CREATE IONS |
| WHAT IS A COVALENT BOND | A BOND THAT RESULTS WHEN ATOMS SHARE ELECTRONS |
| THE MEASURE OF THE ABILITY OF AN ATOM TO ATTRACT ELECTRONS | ELECTRONEGATIVITY |
| RELATE ELECTRONEGATIVITY AND THE PERIODIC TABLE | ELECTRONEG. INCREASES GOING ACROSS AND UP |
| IF THE STRUCTURE IS AN ION, WHAT DO WE DO TO GIVE IT THE PROPER CHARGE? | ADD OR SUBTRACT |
| HOW DO WE CALCULATE FORMAL CHARGE | BY SUBSTRACTING THE NUMBER OF VALENCE ELECTRONS ASSIGNED TO AN ATOM IN ITS BONDED STATE FROM THE NUMBER OF VALENCE ELECTRONS IT HAS AS A NEUTRAL FREE ATOM |
| WHERE CAN THE NUMBER OF VALENCE ELECTRONS BE FOUND IN THE PERIODIC TABLE | GROUP NUMBER |
| THE GREATER THE NUMBER OF NODES, THE ___ THE ENERGY | GREATER |
| ORBITALS OF EQUAL ENERGY ARE SAID TO BE | DEGENERATE ORBITALS |
| WHAT IS A STEREOISOMER | ISOMERS THAT DIFFER ONLY IN THE ARRAGEMENT OF THEIR ATOMS IN SPACE |
| NAME THE CHAR. OF TETRAHEDRAL | 109.5 DEGREES` |
| NAME THE CHAR. OF TRIGONAL PYRAMID | 3 BONDING PAIRS, 1 NONBONDING. 107 DEGREES |
| NAME THE CHAR. OF BENT | 2 BONDING, 2 NONBONDING; 105 DEGREES |
| NAME THE CHAR. OF TRIANGULAR (TRIGONAL PLANAR) | 3 BONDING PAIRS; 120 DEGREES |
| WHAT IS AN EXAMPLE OF SP HYBRIDIZAITON | ALKYNES |
| WHAT IS AN EXAMPLE OF SATURATED | ALKANES |
| WHAT IS AN EXAMPLE OF UNSATURATED | ALKENES AND ALKYNES |
| WHAT IS A HETEROATOM | ATOMS THAT FORM COVALENT BONDS AND HAVE UNSHARED ELECTRON PAIRS |
| HOW ARE ALKYL HALIDES CLASSIFIED | BASED ON THE C ATOM TO WHICH THE HALOGEN IS DIRECTLY ATTACHED |
| HOW ARE ALCOHOLS CLASSIFIED | BASED ON THE DEGREE OF SUBSTITUITION OF THE C TO WHICH THE HYDROXL GROUP IS DIRECTLY ATTACHED |
| HOW ARE AMINES CLASSIFIED | BASED ON THE NUMBER OF ORGANIC GROUPS ATTACHED TO THE N ATOM |
| WHAT WOULD METHANE LOOK LIKE | CH4 |
| WHAT WOULD METHYL LOOK LIKE | CH3-- |
| WHAT WOULD ETHANE LOOK LIKE | CH3CH2 |
| WHAT WOULD ETHYL LOOK LIKE | CH3CH2-- OR C2H5 |
| WHAT WOULD PROPANE LOOK LIKE | CH3CH2CH3 |
| WHAT WOULD PROPYL LOOK LIKE | CH3CH2CH2-- |
| WHAT DOES ISOPROPYL LOOK LIKE | CH3CHCH3 OR CH3CHCH3 (CH3 IS ATTACHED ABOVE) |
| WHEN A BENZENE RING IS ATTACHED TO SOME OTHER GROUP OF ATOMS IN A MOLECULE, IT IS CALLED A | PHENYL GROUP |
| THE COMBINATION OF A PHENYL GROUP AND A CH2 GROUP IS CALLED A | BENZYL GROUP |
| HOW ARE ALKY HALIDES CLASSIFIED | BASED ON THE C ATOM TO WHICH THE HALOGEN IS DIRECTLY ATTACHED |
| NAME THE BONDS IN ORDER OF DECREASING STRENGTH | CATION-ANION, COVALENT, ION-DIPOLE, DIPOLE-DIPOLE (INCLUDING H BONDS) , VAN DER WAALS |
| _____ ARE CHARACTERISTIC OF COMPOUNDS WITH MULTIPLE BONDS | ADDITIONS |
| HETEROLYSIS PRODUCES | IONS |
| HOMOLYSIS PRODUCES | RADICALS |
| WHAT IS HETEROLYSIS | WHEN A COVALENT BOND BREAKS SO THAT ONE FRAGMENT TAKES AWAY BOTH ELECTRONS OF THE BOND, LEAVING THE OTHER FRAGMENT WITH AN EMPTY ORBITAL |
| WHAT IS HOMOLYSIS | WHEN A COVALENT BOND BREAKS SO THAT EACH FRAGMENT TAKES AWAY ONE OF THE ELECTRONS OF THE BOND |
| WHAT DOES HETEROLYSIS REQUIRE | SEPARATION OF CHARGED IONS |
| ACCORDING TO BROWNST-LOWRY, A ___ IS A SUBSTANCE THAT CAN DONATE A PROTON | ACID |
| ACCORDING TO BRONSTED LOWRY, A ___ IS A SUBSTANCE THAT CAN ACCEPT A PROTON | BASE |
| ELECTRON PAIR ACCEPTONS | ACIDS |
| ELECTRON PAIR DONORS | BASES |
| ____ ARE ELECTRON DEFIECENT, AND ARE THEREFORE LEWIS ACIDS | CARBOCATIONS |
| REAGENTS WHICH IN THEIR REACTIONS SEEK THE EXTRA ELECTRONS THAT WILL GIVE THEM A STABLE VALENCE SHELL OF ELECTRONS. ACIDS. | ELECTROPHILES |
| BASES. REAGENTS THAT SEEK A PROTON OR SOME OTHER POSITIVE CENTER | NUCLEOPHILES |
| ACID -BASE REACTIONS ALWAYS FAVOR THE FORMATION OF THE ______ AND ______ | WEAKER ACID AND WEAKER BASE |
| RELATE ACIDITY AND THE PERIODIC TABLE | ACIDITY INCREASES GOING ACROSS AND GOING DOWN |
| _____ WEAKEN AS THE DISTANCE FROM THE SUBSTITUENT INCREASES | INDUCTIVE EFFECTS |
| _____ ARE MUCH MORE ACIDIC THAN THE CORRESPONDING ALCOHOLS | CARBOXYLIC ACIDS |
| ANY FACTOR THAT STABILIZES THE CONJUGATE BASE OF AN ACID ______ THE STRENGTH OF THE ACID | INCREASES |
| WHAT IS A PROTIC SOLVENT | ONE THAT HAS A H ATOM ATTACHED TO A STRONGLY ELECTRONEGATIVE ELEMENT |
| IT IS NOT POSSIBLE TO USE A BASE STRONGER THAN ____ IN AQUEOUS SOLUTION | HYDROXIDE ION |
| BRANCHING OF THE ALKANE CHAIN ____ THE BP | LOWERS |
| BRANCHING THAT PRODUCES HIGHLY SYMMETRICAL STRUCTURES RESULTS IN ____ MP | ABNORMALLY HIGH |
| CYCLOALKANES HAVE MUCH ____ MP THAN THEIR OPEN-CHAIN COUNTERPARTS | HIGHER |
| ____ AND ____ ARE ALMOST TOTALLY INSOLUBLE IN WATER BECAUSE OF THEIR LOW POLARITY AND THEIR INABILITY TO FORM H BONDS | ALAKANES AND CYCLOALKANES |
| WHAT IS THE DIHEDRAL ANGLE BETWEEN STAGGERED CONFORMATIONS | 180 |
| WHAT IS THE ANGLE BETWEEN ECLIPSED CONFORMATIONS | 0 |
| THE ____ DOES NOT HAVE TORISIONAL STRAIN FROM STERIC HINDRANCE | ANTI CONFORMATION |
| THE ____ CONFORMATION IS THE MOST STABLE | ANTI |
| WHICH HAS MORE ENERGY-GAUCHE OR ANTI | GAUCHE |
| THE _____ CONFORMATION HAS THE MOST ENERGY OF ALL | ECLIPSED |
| WHAT IS A CONFORMATIONAL ISOMER | STEREOISOMER THAT IS INTERCONVERTIBLE WITH ONE ANOTHER BY BOND ROTATIONS |
| WHAT DO WE USE TO MEASURE THE RELATIVE STABILITES OF ISOMERS | HEATS OF COMBUSTION |
| THE MORE ____ A MOLECULE POSSESS, THE ____ POTEINTAIL ENERGY IT HAS AND THE ____ STABLE IT IS. | MORE RING STRAIN, THE MORE POTENTIAL ENERGY, THE LESS STABLE |
| WHAT IS THE MOST STABLE CONFORMATION OF CYCLEHEXANE | CHAIR CONFORMATION |
| WHAT IS THE ANGLE OF CHAIR | 109.5 |
| WHAT CONFORMATION OF CYCLOHEXANE IS FREE OF ANGLE STRAIN | CHAIR AND BOAT |
| WHAT CONFORMATION OF CYCLOHEXANE IS FREE OF TORSIONAL STRAIN | CHAIR ONLY |
| WHICH HAS HIGHER ENERGY: CHAIR OR BOAT | BOAT |
| WHICH IS MORE STABLE: CHAIR OR BOAT | CHAIR |
| WHICH IS MORE FLEXIBLE: CHAIR OR BOAT | BOAT |
| WHICH HAS A LOWER ENERGY: BOAT OR TWIST | TWIST |
| ARE THE PHYSICAL PROPERTIES OF CIS-TRANS ISOMERS THE SAME OR DIFFERENT | DIFFERENT |
| ONE THAT CANNOT BE PLACED ON ITS MIRROR IMAGE SO THAT ALL PARTS COINCIDE | CHIRAL |
| NOT SUPERPOSABLE ON ITS MIRROR IMAGE | CHIRAL |
| WHAT ARE ENANTIOMERS | STEREOISOMERS WHOSE MOLECULES ARE NONSUPERPOSABLE MIRROR IMAGES OF EACHOTHER |
| WHAT ARE DIASTEROMERS | STEREOISOMERS WHOSE MOLECULES ARE NOT MIRROR IMAGES OF EACHOTHER |
| WHICH CAN PRODUCE ENANTIOMERS: CHIRAL OR ACHIRAL | CHIRAL |
| OBJECTS THAT ARE SUPERPOSABLE ON THEIR MIRROR IMAGE | ACHIRAL |
| ALL MOLECULES WITH A PLANE OF SYMETRY ARE | ACHIRAL |
| CLOCKWISE | R |
| COUNTERCLOCKWISE | S |
| ENANTIOMERS HAVE ____ MELTING AND BP | INDENTICAL |
| SEPERATE ENANTIOMERS ARE SAID TO BE OPTICALLY ___ COMPOUNDS | ACTIVE |
| A SUBSTANCE THAT ROTATES PLANE POLARIZED LIGHT IN THE CLOCKWISE DIRECTION IS ALSO SAID TO BE | DEXTROROTATORY |
| ONE THAT ROTATES PLANE POLARIZED LIGHT IN A COUNTERCLOCKWISE DIRECTION IS SAID TO BE | LEVOROTAROY |
| AN EQUIMOLAR MIXTURE OF TWO ENANTIOMERS | RACEMIC |
| REACTIONS CARRIED OUT WITH ACHIRAL REACTANTS CAN OFTEN LEAD TO ___ PRODUCTS | CHIRAL |
| THE TOTAL NUMBER OF STEREOISOMERS WILL NOT EXCEED: | 2^N; N IS THE NUMBER OF TETRAHEDRAL STEREOGENIC CENTERS |
| DIASTEROMERS HAVE ___ PHYSICAL PROPERTIES | DIFFERENT |
| MESO COMPOUNDS ARE CHIRAL OR ACHRIAL | ACHIRAL |
| MESO COMPOUNDS ARE OPTICALLY ____ | INACTIVE |
| WHAT IS A MESO COMPOUNDS | MOLECULE THAT IS NOT CHIRAL EVEN THOUGH IT CONTAINS TETRAHEDRAL ATOMS WITH FOUR DIFFERENT GROUPS ATTACHED. |
| VERTICAL LINES REPREESENT BONDS THAT PROJECT | BEHIND THE PLANE OF THE PAPER |
| HORIZONTAL LINES REPRESENT BONDS THAT PROJECT | OUT OF THE PLANE OF THE PAPER |
| A SPECIES WITH AN UNSHARED ELECTRON PAIR | NUCLEOPHILE |
| WHAT IS A NUCLEOPHILE | A REAGENT THAT SEEKS A POSITIVE CENTER; ANY NEGATIVE ION OR ANY NEATRUAL MOLECULE THAT HAS AT LEAST ONE UNSHARED ELECTRON PAIR |
| TO ACT AS THE SUBSTRATE, A MOLECULE MUST: | HAVE A GOOD LEAVING GROUP |
| WHAT IS A GOOD LEAVING GROUP | A SUBSTITENT THAT CAN LEAVE AS A RELATIVELY STABLE, WEAKLY BASIC MOLECULE OR ANION. (WEAK BASE, STABLE ANION) |
| WHAT IS STERIC HINDRANCE | THE SPATIAL ARRANGEMENT OF THE ATOMS OR GROUPS AT OR NEAR THE REACTING SITE OF A MOLECULE HINDERS OR RETARDS A REACTION. |
| alkenes and alkynes dissolve in _____ solvents or in solvents of low polarity | nonpolar |
| alkenes and alkynes are only slightly soluble in | water |
| in the EZ system, a trans molecule would be | E |
| in the EZ system, a cis molecule would be | Z |
| do cis and trans isomers of alkenes have the same stability | no |
| in alkenes, are cis or trans isomers more stable | trans are more stable |
| why is the trans alkene isomer more stable than the cis | because strain caused by crowding of two alkyl groups on the same side of the double bond in cis conformations |
| the ____ the number of alkyl groups attached, the greater is the alkenes stability | greater |
| what is the most stable alkene | tetrasubstitued |
| what is the least stable alkene | unsubstituted |
| the rings of cycloalkenes containing five carbon atoms or fewer exist only in what form | cis |
| ____ reactions are the most important means for synthesizing alkenes | elimination |
| the best reaction conditions to use when synthesizing an alkene by dehydrohalogenation are those that promote what kind of reaction | E2 |
| when synthezing alkenes by an E2 mechanism, if you must begin with a primar alkyl halide, what should be used | a bulky base-strong, relatively unpolarizable |
| dehyrohalogenation of many _____ leads to more than one product | alkyl halides |
| what is Zaitseves Rule? | formation of the most substitued alkene is favored with a small base AND whenever an elmination reaction occurs to give the most stable, most highly substitued alkene |
| using Z's rule, what would be the major product? | more stable alkene |
| how do form the least stable alkene when carrying out a dehydrohalogenation reaction | use a bulky base |
| what is the Hofmann rule | when an elimination reaction yields the less substituted alkene |
| the five atoms involved in the transition state of a ____ reaction must lie in the same plane | E2 |
| what is the preferred transition state in E2 reactions and why? | anti coplanar; because it is staggered, and therefore in lower energy |
| the syn coplanar transition state in E2 reactions is | eclipsed |
| what is the easiest alcohol to dehydrate | tertiary alcohols |
| how do you dehyrdate secondary and tertiary alcohols | by an E1 reaction in which the substrate is a protonated alcohol |
| a compound bearing the halogens on adjacent carbons | vic-dihalides |
| the hydrogen bonded to the carbon of a terminal alkyne is considerably more ____ than those bonded to teh carbons of an alkene or alkane | acidic |
| in termical alkynes, what is the order of basicity | exactly opposite that of their relative acidity |
| what is catalytic hydrogenation | the process of adding a hydrogen to an alkene |
| hydrogenation of an alkene is what kind of reaction | exothermic |
| when both hydrogen atoms add from the same side of the molecule | syn addition |
| addition that places the parts of the adding reagent on opposite faces of the reactant | anti addition |
| hydrogenation of alkynes in the presence of what catalyst causes a syn addition of hydrogen to take place | P-2 catalyst |
| alkenes whose molecules contain only one double bond have the general formula | CnH2n |
| alkynes and alkenes with two double bonds have the general formula | CnH2n-2 |
| hydrocarbons with one triple bond and one double bond and alkenes with three double bonds have the general formula | CnH2n-4 |
| the number of pairs of H atoms that must be subtracted from the molecular formula of the corresponding alkane to give the molecular formula of teh compound under consideration | index of hydrogen deficiency |
| in IHD, for compounds containing halogen atoms, what do we do | count the halogen atoms as though they were hydrogen atoms |
| if IHD = 1 what does that mean | that it could have either one ring or one double bond |
| in IHD, for compounds containing oxygen, what do we do | ignore the oxygen atoms |
| in IHD, for compounds containing nitrogen atoms, what do we do | subtract one H for each N atom and then we ignore the N atoms |
| what kind of reaction is characteristics of an atom with C to C double bonds | addition |
| addition reactions are usually exothermic or endothermic | exothermic |
| what is Markovnikovs rule? | in the addition of HX to an alkene, the H atom adds to the C atom of the double bond that already has the greater number of H atoms |
| when a reaction can potentially yeild two or more constitutional isomers actually produces only one, the reaction is said to be: | regioselective |
| when water and mercuric accetate add to the double bond | oxymercuration |
| when sodium borohydride reduces the acetoxymercury group and replaces it with H | demercuration |
| the ____ and ___ steps take place with retention of configuration | oxidation and hydrolysis |
| a reaction is ____ when a particular steroisomeric form of the starting material reacts in such a way that it gives a specific steroisomeric form of the product | stereospecific |
| the position of an NMR signal relative to TMS | chemical shift |
| indicates the number of H atoms on adjacent carbons | signal splitting |
| the chemical shift can be described as: | downfield or upfield (smaller values) |
| signals result from what two things | deshielding and shielding |
| decreased electron density around a nucleus | deshielding |
| higher electron density around a nucleus | shielding |
| deshielding can be caused by | electron withdrawing groups |
| shielding can be caused by | electron donating groups |
| In NMR, if n=0, it leads to a | singlet |
| in NMR, if n=1, it leads to a | doublet |
| in NMR if n=2, it leads to a | triplet |
| in NMR if n=3 it leads to a | quartet |
| what rule do we use for signal splitting | the n + 1 rule, where n equals the number of equivalent H atoms seperated by three or fewer bonds |
| define homotopic nuclei | lead to the same compound if substituted |
| define enatiotopic nuclei | lead to enantiomers if substituted |
| define diastereotopic nuclei | lead to diastereomers if substituited |
| what do homotopic and enantiotopic have in common | have the same chemical shift but do no split eachothers signals |
| what do two diastereotopic nuclei have in common | have different chemical shifts and split each others signals |
| what is the nomenclature used for ethers | list in alphabetical order both groups that are attached to the oxygen atom and add the word ether |
| describe the nomenclature used for alcohols | the hydroxyl group takes precedence over double bonds and triple bonds in deciding which functional group to name as the suffix. |
| do alcohols have higher or lower boiling points than ethers and hydrocarbons | higher |
| the molecules of alcohols can associate with eachother through what kind of bonds | hydrogen bonds |
| if you want to hydrate a double bond in a Markovnikov orientation, what two methods would u use | oxymercuration-demercuration and acid-catalyzed hydration |
| if u want to hydrate a double bond with an anti-M orientation, what do u use | hydroboration-oxidation |
| if u want to add HX to a double bond in a Markovinkov sense, what do we treat the alkene with | HF, HCL, HBr or HI |
| if we want to add HBr in an anti-M orientation, what do we treat the alkene with | HBr and a peroxide |
| what can we add to a double bond to get an anti addition | bromine or chlorine |
| if we want to carry out syn 1,2-dihydroxylation of a double bond, what do we use | KMnO4 in cold, dilute and basic solution or OsO4 followed by NaHSO3 |
| anti 1,2-dihydroxylation of a double bond can be achieved how | converting the alkene to an epoxide and then carrying out an acid-catalyzed hydrolosis |
CADD 2 Honors
