orgo chem

Question 1

geminal diols what

Answer 1

spontaneously dehydrate (lose water molec) to produce carbony comounds

Question 2

diols with hydroxyl groups on the same carbon are called _____, and diols with hydroxyl groups on adjacent carbons are called ___

Answer 2

geminal (hydrates)
vicinal
diols

Question 3

alcohols with two hydroxyl groups are called what

Answer 3

diols
or glycols

Question 4

esters are what

Answer 4

carboxylic acid derivatives

Question 5

____ isomers are the least similar of all isomers

Answer 5

structural

Question 6

what do structural isomers share?

Answer 6

molecular formual - molecular weight is the same

Question 7

physical properties

Answer 7

characteristics of processes that dont change the composition of matter,s uch as melting point, boiling point, soubility, odor, colour and density

Question 8

chemical properties

Answer 8

reactivity of molecule with other molecules and result in changes in chemical composition

in organic chem, this is mostly in functional groups

Question 9

stereoisomers share what

Answer 9

atomic connectivity - same structural backbone

Question 10

conformational isomers

Answer 10

differ in rotation around single bonds

Question 11

configurational isomers

Answer 11

can be interconverted only by breaking bonds

Question 12

anti conformation

Answer 12

staggered - two largest groups are antiperiplanar (same plane, opposite sides) - most energetically favourable type of staggered conformation (lowest energy state)

Question 13

gauche

Answer 13

two largest groups are 60 degrees apart

Question 14

totally eclipsed is what energy state?

Answer 14

highest

Question 15

ring strain factors

Answer 15

angle strain, torsional strain, and nonbonded strain (steric strain)

Question 16

angle strain

Answer 16

results when bond angles deviate from their ideal values by being stretched or compressed

Question 17

torsional strain

Answer 17

cyclic molecules must assume conformations that have eclipsed or gauche interactions

Question 18

nonbonded strains (vdw)

Answer 18

nonadjacent atoms or groups compete for same space

dominant source of steric strain in flagpole interactions

Question 19

cyclohexane three main conformaions

Answer 19

chair
boat
twist (skew boat)

Question 20

hydrogen atoms that are perpendicular to plane of ring

Answer 20

axial

Question 21

hydrogen atoms that are parallel

Answer 21

equatorial

Question 22

chiral if wht

Answer 22

mirror image cannot be superimposed on original object

Question 23

enantiomers have nearly identical ______ proerites and chemical peoperties, but they rotate ________ light in opposite directions and react differently in chiral environments

Answer 23

physical
plane polarized light

Question 24

d- or + to refer to _______ rotation, l- and - to refer to ______ rotation

Answer 24

clockwise
counterclockwise

Question 25

racemic mixture displays ____ optical activity

Answer 25

no

Question 26

meso compound

Answer 26

a molec with chiral centers that has an internal plane of symmetry two halves that are mirror images - thus as a whole they are not optically active

Question 27

relative configuration of chiral molecule

Answer 27

configuration in relation to another chiral molecule

Question 28

absolute conformation of chiral molec

Answer 28

exact spatial arrangement of these atoms or gruops - independent of other molecules

Question 29

priority in e and z formation / designation is assigned based on what

Answer 29

atom bonded to double bonded carbosn - higher the atomic number, higher the priority

Question 30

alkene is named _____, if the two highest priority substients on each carbon are the same side of the double bond,

Answer 30

Z

Question 31

if two highest priority substituents are on opposite sides, they are named ___

Answer 31

E

Question 32

when drawing the circle for r and s, if the roation is counterclockwise, then it is called what and what if it is clockwise

Answer 32

S R

Question 33

s and p orbital shapes

Answer 33

s - spherical and symmetrical centered around nucleu p - composed of two lobes located symmaetrically about the nucleus and contains a node - area where probability of finding an e- is zero

Question 34

if the signs of the wae functions are the same, a lower energy more stable ____ orbital is produced, and if they are different, a higher energy (less stable) ____ orbital is prodcued

Answer 34

bonding antibonding

Question 35

how are sigma bonds formed?

Answer 35

head-to-head or tail-to-tail overlap of atomic orbitals - most common bond in organic compounds and on MCAT

Question 36

single bonds are what kind of bond

Answer 36

sigma bonds

Question 37

pi bond formation how

Answer 37

when two p orbitals line up in a parallel fashion - e- cloud overlaps

Question 38

what forms a double and triple bond

Answer 38

double is pi on top of sigma tripe is sigma and two pi

Question 39

which is weaker pi or sigma?

Answer 39

pi bonds are weaker strength is additive though - double and triple bonds are stronger than single

Question 40

conjugation requires alternating single and multiple bonds because this pattern __________ down the backbone of the molecule

Answer 40

aligns a number of unhybridized p orbitals

Question 41

____ electrons can delocalize through p-orbital system, adding ___ to the molec

Answer 41

pi stability

Question 42

lewis acid is what

Answer 42

e- acceptor

Question 43

lewis base is what

Answer 43

e- donor

Question 44

bronsted lowry acid

Answer 44

e- donor

Question 45

bronsted lowry base

Answer 45

e- acceptor

Question 46

nucleophiles tend to have ______ or ____ bonds that can be used to form covalent bonds to electrophiles

Answer 46

lone pairs pi

Question 47

how can you identify nucleophiles (most)

Answer 47

carbon, hydrogen, oxygen, or nitrogen (CHON) with a minus sign or lone pair

Question 48

nucleophilicity is determined by four major factors which are

Answer 48

charge - nucleophilicity increases with increasing electron density - more negative charge electronegativity - nucleophilicity decreases as EN increases because these atoms are less likely to share e- density steric hindrance - bulkier molecues are less nucleophilic solvent - protic solvents can hinder nucleophilicity by protonating the nucleophile or through hydrogen bonding

Question 49

leaving groups

Answer 49

molecular fragments that retain e- after heterolysis

Question 50

nucleophilic attack will only occur when

Answer 50

if the reactants are more reactive than the products

Question 51

steric hindrance

Answer 51

describes prevention of rxns at particular location within molecule due to size of substuent groups

Question 52

primary secondary tertiary alcohols being oxidized to what

Answer 52

primary - aldehydes secondary - ketons tertiary - cannot be oxidized bc they are already as oxidized as they can be without breaking a carbon-carbon bond

Question 53

jones oxidation

Answer 53

chromium trioxide Cro3 - dissolved with dilute sulfuric acid in acetone

Question 54

treatment of phenols with oxidizing agents produces compounds called what

Answer 54

quinones

Question 55

hydroxyquinone vs hydroquinone`

Answer 55

contains two carbonyls and a variable number of hydroxyl groups benzene ring with two hydroxyl groups

Question 56

electron withdrawing groups like oxygen stabilize what and what destabilizes th same ting

Answer 56

organic anions electron donating groups like alkyl groups

Question 57

ketones are slighltly less likely to reat with nucleophiles because what

Answer 57

extra alkyl group destabilizes the carbanion and increase steric hindrance

Question 58

are carboxylic acids polar

Answer 58

yesc

Question 59

carboxylic acid acidity is due to what

Answer 59

resonance stabilization and can be enhanced by addition of electronegative groups or greater ability to delocalize charge

Question 60

which hydrogen is the most acidic proton on a carboxylic acid?

Answer 60

hydroxyl hydrogens

Question 61

protonating the c=o makes electrophilic carbon what

Answer 61

even more ripe for nucleophilic attack

Question 62

conjugated molex

Answer 62

molecs with unhybridized p orbitals

Question 63

UV spectroscopy is most useful for what

Answer 63

studyign compounds containing double bondns or heteroatoms with lone pairs that create conjugated systems

Question 64

in proton nmr, each peak or group of peaks that are part of a mulitplet represents what

Answer 64

single group of equivalent protons

Question 65

splitting of a peak in proton nmr represents what

Answer 65

the number of adjacent hydrogens peak will be split into n+1 subpeaks where n is number of adjacent hydrogens

Question 66

proton nmr is good for what

Answer 66

determining relative no. of protons and their relative chemical elements showing how many adjacent protons thera re by splitting patterns inferring certain functional groups

Question 67

solubility based extraction procedures

Answer 67

extraction filtration recrystallization

Question 68

amides are formed how

Answer 68

condensation reaction of other carboxylic acid derivatives and ammonia or an amine

Question 69

cyclic amides are called what

Answer 69

lactams

Question 70

esters are formed how

Answer 70

by the condensation reaction of carboxylic acids or anhydrides with alcohols

Question 71

anhydrides are formed how

Answer 71

by condenstation reaction of two carboxylic acids

Question 72

steric hindrance

Answer 72

when a reaction doesn't proceed due to the size of the substituents