Ochem - Ch2 - Exam 1

Front 1

an acid derivative with a chlorine atom in place of the hydroxyl group

Back 1

acid chloride

Front 2

a compound that contains a hydroxyl group;
R -- OH

Back 2

alcohol

Front 3

a carbonyl group with one alkyl group and one hydrogen

Back 3

aldehyde

Front 4

hydrocarbons containing only single bonds

Back 4

alkanes

Front 5

hydrocarbons containing C = C double bonds

Back 5

alkenes

Front 6

hydrocarbons containing C - C triple bonds

Back 6

alkynes

Front 7

a hydrocarbon group with only single bonds; an alkane with one hydrogen removed, to allow bonding to another group; symbolized by R

Back 7

alkyl group

Front 8

an acid derivative that contains an amine instead of the hydroxyl group of the acid.

Back 8

amide

Front 9

an alkylated analogue of ammonia;
R -- NH2
R2NH
R3N

Back 9

amine

Front 10

hydrocarbons containing a benzene ring, a six-membered ring with three double bonds

Back 10

aromatic hydrocarbons (arenes)

Front 11

a measure of the polarity of an individual bond in a molecule, defined as u = (4.8 * d * S), where u is the dipole moment in debyes, d is the bond length in angstroms, and S is the effective amount of charge separated, in units of electronic charge

Back 11

bond dipole moment

Front 12

the functional group, as in a keton or aldehyde

Back 12

carbonyl group

Front 13

the -COOH functional group

Back 13

carboxyl group

Front 14

a compound that contains the carboxyl group
R - COOH

Back 14

carboxylic acid

Front 15

stereoisomers that differ in their cis-trans arrangement on a ring or a double bond.

Back 15

cis-trans isomers (geometric isomers)

Front 16

has similar groups on the same side

Back 16

cis isomer

Front 17

has similar groups on opposite sides

Back 17

trans isomer

Front 18

isomers whose atoms are connected differently; they differ in their bonding sequence

Back 18

constitutional isomers (structural isomers)

Front 19

the --CN: (triple bond) functional group, as in a nitrile

Back 19

cyano group

Front 20

attractive intermolecular forces resulting from the attraction of the positive and negative ends of the molecular dipole moments of polar molecule

Back 20

dipole-dipole forces

Front 21

bond containing four electrons etween two nuclei. one pair of electrons forms a sigma bond, and the other pair forms a pi bond

Back 21

double bond

Front 22

an acid derivative with an alkyl group replacing the acid proton

Back 22

ester

Front 23

a compound with an oxygen bonded between two alkyl groups; R -- O -- R'

Back 23

ether

Front 24

the reactive, nonalkane part of an organic molecule

Back 24

functional group

Front 25

a directional orbital formed from a combination of s and p orbitals on the same atom. two orbitals are formed by sp hybridization, three orbitals by sp2 hybridization, and four orbitals by sp3 hybridization.

Back 25

hybrid atomic orbital

Front 26

gives a bond angle of 180 degrees and linear geometry

Back 26

sp hybrid orbitals

Front 27

gives a bond angle of 120 degrees and trigonal geometry

Back 27

sp2 hybrid orbitals

Front 28

gives bond angles of 109.5 degrees and tetrahedral geometry

Back 28

sp3 hybrid orbitals

Front 29

compounds composed exclusively of carbon and hydrogen

Back 29

hydrocarbons

Front 30

hydrocarbons containing only single bonds

Back 30

alkanes

Front 31

hydrocarbons containing C = C double bonds

Back 31

alkenes

Front 32

hydrocarbons containing C - C triple bonds

Back 32

alkynes

Front 33

alkanes, alkenes, and alkynes in the form of a ring

Back 33

cycloalkanes, cycloalkenes, cycloalkynes

Front 34

hydrocarbons containing a benzene ring, a six-membered ring with three double bonds

Back 34

aromatic hydrocarbons

Front 35

a particularly strong attraction between a nonbonding pair of electrons and an electrophilic O-H or N-H hydrogen. Have bond energies of about 5 kcal/mol, compared with about 100 kcal/mol for typical C-H bonds.

Back 35

hydrogen bond

Front 36

the -OH functional group, as in an alcohol

Back 36

hydroxyl group

Front 37

different compounds with the same molecular formula

Back 37

isomers

Front 38

a carbonyl group with two alkyl groups attached

Back 38

ketone

Front 39

wave functions can add to each other to produce the wave functions of new orbitals. The number of new orbitals generated equals the original number of orbitals

Back 39

linear combination of atomic orbitals (LCAO)

Front 40

intermolecular forces resulting from the attraction of correlated temporary dipole moments induced in adjacent molecules

Back 40

London dispersion forces

Front 41

the vector sum of the bond dipole moments (and any nonbonding pairs of electrons) in a molecule; a measure of the polarity of a molecule

Back 41

molecular dipole moment

Front 42

an orbital formed by the overlap of atomic orbitals on different atoms. Can be either bonding or antibonding, but only the bonding are filled in most stable molecules.

Back 42

molecular orbital (MO)

Front 43

places a large amount of electron density in the bonding region between the nuclei. The energy of an electron in ---- is lower than it is in an atomic orbital

Back 43

bonding molecular orbital

Front 44

places most of the electron density outside the bonding region. The energy of an electron in an --- is higher than it is in an atomic orbital

Back 44

antibonding molecular orbital

Front 45

a compound containing a cyano group.
-- CN: (triple bond)

Back 45

nitrile

Front 46

in an orbital, a region of space with zero electron density

Back 46

node

Front 47

bond formed by sideways overlap of two p orbitals. Has its electron density in two lobes, one above and one below the line joining the nuclei.

Back 47

pi bond

Front 48

a bond with most of its electron density centered along the line joining the nuclei; a cylindrically symmetrical bond. Normally single bonds.

Back 48

sigma bond

Front 49

study of the structure and chemistry of stereoisomers

Back 49

stereochemistry

Front 50

isomers that differ only in how their atoms are oriented in space

Back 50

stereoisomers

Front 51

isomers whose atoms are connected differently; they differ in their bonding sequence

Back 51

structural isomers (IUPAC term: constitutional isomer)

Front 52

a bond containing six electrons between two nuclei. One pair of electrons forms a sigma bond and the other two pairs form two pi bonds at right angles to each other

Back 52

triple bond

Front 53

bonds and lone pairs around a central atom tend to be separated by the largest possible angles: about 180 degrees for two, 120 degrees for three, and 109.5 degrees for four.

Back 53

valence-shell electron-pair repulsion theory (VSEPR theory)

Front 54

the attractive forces between neutral molecules, including dipole-dipole forces and London forces

Back 54

van der Waals forces

Front 55

the forces between polar molecules resulting from attraction of their permanent dipole moments

Back 55

dipole-dipole forces

Front 56

intermolecular forces resulting from the attraction of correlated temporary dipole moments induced in adjacent molecules

Back 56

London forces

Front 57

the mathematical description of an orbital. the square of the --- is proportional to the electron density

Back 57

wave function

Front 58

two general kinds of waves

Back 58

traveling waves
standing waves

Front 59

sound waves that carry a thunderclap

Back 59

traveling waves

Front 60

vibrate in a fixed location

Back 60

standing waves

Front 61

an electron in an atomic orbital is like a stationary, bound vibration

Back 61

standing wave

Front 62

when one is displaced upward, the other wave is displaced downward

Back 62

out of phase

Front 63

when orbitals on DIFFERENT atoms interact, they produce --- that lead to bonding (or antibonding)

Back 63

molecular orbitals

Front 64

when orbitals on the SAME atom interact, they give --- that define the geometry of the bonds

Back 64

hybrid atomic orbitals

Front 65

the stability of a covalent bond results from a large amount of --- in the ---, the space between the two nuclei

Back 65

electron density
bonding region

Front 66

electrons close to both nuclei results in --- of the overall energy

Back 66

lowering

Front 67

the internuclear distance where attraction and repulsion are balanced, which also gives the minimum energy (the strongest bond)

Back 67

bond length

Front 68

1s wave functions reinforce each other

Back 68

constructive

Front 69

wave functions cancel out where they overlap

Back 69

destructive

Front 70

when wave functions reinforce each other and increase the electron density the result is ---.

Back 70

bonding molecular orbital (bonding MO)

Front 71

when wave functions overlap out of phase the result is ---.

Back 71

antibonding molecular orbital

Front 72

when the 1s orbitals are IN phase, the resulting molecular orbital is a ---, with --- energy than that of a 1s atomic orbital.

Back 72

sigma bonding MO
lower

Front 73

When two 1s orbitals overlap OUT OF PHASE, they form an --- with --- energy than that of a 1s atomic orbital.

Back 73

antibonding orbital
higher

Front 74

in stable molecules, the antibonding orbitals are usually ----

Back 74

vacant

Front 75

When two p orbitals overlap along the ling between the nuclei, a(n) --- orbital and a(n) ---- orbital result.

Back 75

bonding
antibonding

Front 76

most of the electron density is centered along the ---.

Back 76

line between the nuclei

Front 77

overlap of an s orbital with a p orbital gives a --- and an ----.

Back 77

bonding MO
antibonding MO

Front 78

p orbitals are oriented at -- degrees

Back 78

90

Front 79

-- degrees is the largest possible separation for four pairs of electrons

Back 79

109.5

Front 80

-- degrees is the largest separation for three pairs of electrons

Back 80

120

Front 81

-- degrees is the largest separation for two pairs of electrons

Back 81

180

Front 82

sp hybridization results in --- bonding and a bond angle of -- degrees

Back 82

linear
180

Front 83

sp2 hybrid orbitals composed of one -- and two -- orbitals; results in -- bonding and bond angles of -- degrees

Back 83

s
p
trigonal
120

Front 84

sp3 are when --- bonds are oriented as far apart as possible, they form a --- shape and --- degree bond angles. It is a combination of the -- orbital with --- -- orbitals

Back 84

4
tetrahedral
109.5
s
3 p

Front 85

pz orbital should look like it points -- and -- of the page

Back 85

in and out

Front 86

dashed lines indicate bonds that

Back 86

go backward

Front 87

wedge shaped bonds indicate bond that

Back 87

come forward

Front 88

straight lines are bonds that

Back 88

are in the plane of the page

Front 89

2 hybrid orbitals
s + p = sp hybridization
??? geometry
???? bond angle

Back 89

linear
180 degrees

Front 90

3 hybrid orbitals
s + p + p = sp2 hybridization
??? geometry
??? bond angle

Back 90

trigonal
120 degrees

Front 91

4 hybrid orbitals
s + p + p + p = sp3 hybridization
??? geometry
??? bond angle

Back 91

tetrahedral
109.5 degrees

Front 92

differs only in rotations about a single bond

Back 92

conformations

Front 93

rotation about single bonds is allowed, but --- are rigid and cannot be twisted

Back 93

double bonds

Front 94

bond dipole moment formula

Back 94

u = S * d
u = 4.8 * S(electron charge) * d

Front 95

C-N dipole moment
-->

Back 95

.22 D

Front 96

C-O dipole moment
-->

Back 96

.86 D

Front 97

C--F dipole moment
-->

Back 97

1.51 D

Front 98

C--Cl dipole moment
-->

Back 98

1.56 D

Front 99

C--Br dipole moment
-->

Back 99

1.48 D

Front 100

C--I dipole moment
-->

Back 100

1.29 D

Front 101

H--C dipole moment
-->

Back 101

.3 D

Front 102

H--N dipole moment
-->

Back 102

1.31 D

Front 103

H--O dipole moment
-->

Back 103

1.53 D

Front 104

C=O dipole moment
-->

Back 104

2.4 D

Front 105

C-triplebond-N dipole moment
-->

Back 105

3.6 D

Front 106

3 major kinds of attractive forces cause molecules to associate into solids and liquids

Back 106

-dipole-dipole forces of polar molecules
-London forces that affect all molecules
-hydrogen bonds that link molecules having -OH or -NH groups

Front 107

polar substance dissolve in ----

Back 107

polar solvents

Front 108

nonpolar substance dissolve in ---

Back 108

nonpolar solvents

Front 109

1 carbon

Back 109

methane

Front 110

2 carbons

Back 110

ethane

Front 111

3 carbons

Back 111

propane

Front 112

4 carbons

Back 112

butane

Front 113

5 carbons

Back 113

pentane

Front 114

6 carbons

Back 114

hexane

Front 115

7 carbons

Back 115

heptane

Front 116

8 carbons

Back 116

octane

Front 117

9 carbons

Back 117

nonane

Front 118

10 carbons

Back 118

decane

Front 119

major components of heating gases, undergo few reactions

Back 119

alkanes

Front 120

triple bond is --- (geometric)

Back 120

linear

Front 121

strongly polar
miscible with water
R - OH

Back 121

alcohol

Front 122

polar
no O - H
R - O - R'

Back 122

ether

Front 123

strongly polar
somewhat soluble in water
miscible with water
RCOR'

Back 123

ketone

Front 124

strongly polar
somewhat soluble in water
miscible with water
RCHO

Back 124

aldehyde

Front 125

R - COOH
pKa ~ 5
resonance stabilized
strongly polar
soluble in water
miscible with water

Back 125

carboxylic acid

Front 126

R - CONH2
most stable acid derivative
not as basic as amine
very weak base

Back 126

amide

Front 127

R - COCl

Back 127

acid chloride

Front 128

R - COOR'

Back 128

ester

Front 129

basic
Kb~ 10 ^-3
R - :NH2
R - :NH - R'
R - :N - R"
|
R'

Back 129

amine

Front 130

R - CN: (triple bond)
contains cyano group

Back 130

nitrile