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Constitutional isomers

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103 Terms

1

Constitutional isomers

share the same molecular formula but have different connectivity of atoms and different physical properties

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2

Covalent Bond

results when two atoms shares a pair of electrons

are illustrated using lewis strictures which electrons are represented by dots

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3

Induction

these are exhibited by polar covalent bonds causing a partial negative or partial positive charge , these can be shown in electrostatic potential maps

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4

Valence Bond theory

treats every bond as the sharing of electron density between two atoms as a result of constructive interference of their atomic orbitals

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5

Molecular Orbital theory

uses Math method to form molecular orbitals each one is associated with the entire molecule rather than just two atoms

Bonding MO - constructive interference between its two atomic orbitals

Antibonding MO- results from destructive interference

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6

Atomic Orbital

is a region of space associated with an individual atom, while a molecular orbital is associated with an entire molecule

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7

Bond line Structures contain dashes and wedges what do these groups represent

wedges - represents a group coming out of the page

dashes- represent a group behind the page

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8

what does resonance stability refer to

it refers to the delocalization of electrons via resonance

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9

Resonance structures are most easily drawn by looking for the following patterns

  1. an allylic lone pair

  2. an allylic carbocation

  3. a lone pair adjacent to C+

  4. a pi bond between two atoms of differing electronegativity

  5. Conjugated pi bonds enclosed in a ring

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10

Rules to Identify the significance of resonance structures

  1. the most significant resonance forms have the greatest number of filled octets

  2. the structure with fewer formal charges is more significant

  3. a structure with a negative charge on the more electronegative element Will be more significant ,similarly , a positive charge will be more stable on the less electronegative element

  4. resonance forms that have equally good lewis structures are described as equivalent and contribute equally to the resonance hybrid

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11

Bronsted- Lowry Acid

is a proton donor

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12

Bronsted-Lowry Base

is a proton acceptor

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13

a strong acid has a LOW

PKA

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14

a weak acid has a HIGH

PKA , this is favored by equilibrium

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15

factors to consider when comparing the stability of anionic conjugate bases

  1. which atom bears the charge

  2. resonance which will stablize a negative charge

  3. induction - electron withdrawing groups such as halogens stablize a nearby charge via induction

  4. orbitals - a negative charge in an sp-hybridized orbital will be closer to the nucleus and more stable than a negative charge in an sp3 hybridized orbital

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16

Cations

positively charged species

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17

Lewis Acid

is an electron pair acceptor

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18

Lewis Base

is an electron pair donor

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19

Alkanes / Saturated hydrocarbons

hydrocarbons that lack pi bonds

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20

Naming Rules

  1. identify parents chain

  2. name the subtituents

  3. number the carbons of the parent and assign a locant number to each substituent

  4. assemble the substituents alphabetically placing locants in front of each substituent for identical ones your di,tri,tetra,penta,hexa

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21

bicycloalkanes

is an alkane that has two rings that are connected to one another

to number the parent , travel first along the longest path connecting the bridgeheads

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22

equilibrium will favor the chair conformation with substituent in the _____ position

Equatorial position ,

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23

Stereoisomers

have the same connectivity of atoms but different in their spatial arrangement

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24

Chiral

not superimposable and have 4 different groups attached to their centers

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25

Enantiomer

a compound with one chiral center will have one non superimposable mirror image, mirror images

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26

racemic mixture

a solution containing equal amounts of both enantiomers

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27

formula for finding the number of stereoisomers

2^n , n= the number of chiral centers

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28

meso compound

contains multiple chiral centers but is achiral because it possesses reflectional symmetry

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29

Fisher projections

are drawings that convey the configuration of chiral centers without the use of wedges and dashes

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30

heat of reaction

is a measure of the energy exchanged between the system and its surroundings

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31

bond dissociation energy

the amount of energy necessary to accomplish hemolytic bond cleavage

producing radicals

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32

Exothermic reactions

involve a transfer od energy from the system to the surroundings

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33

Endothermic Reactions

involve the transfer of energy from the surrounding into the system

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34

Entropy

the disorder of a system

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35

A low energy of activation corresponds with

a fast rate

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36

Catalyst

speed up the rate of reaction by providing an alternate pathway with lower Ea

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37

On an energy diagram what does each Peak and valley stand for

Peak- transition state

Valley - intermediate

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38

Nucleophile

is an electron rich molecule or ion that is capable of donating a pair of electrons known as Lewis Bases

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39

Electrophile

is an electron-deficient molecule or ion that is capable of accepting a pair of electrons known as Lewis Acid

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40

Carbocation

are ions In which a carbon atom bears a positive charge as a result of a an empty p orbital and are electrophlilic

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41

Types of arrow pushing patterns

  1. Nucleophilic attack

  2. loss of a leaving group

  3. proton transfer

  4. rearrangement

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42

what is the most common type of rearrangement

is a carbocation rearrangement in which a carbocation undergoes a hydride or methyl shift to produce a more stable carbocation tertiary carbocations are the most stable

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43

what are good leaving groups

conjugated bases of strong acids

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44

Alpha positon

is the carbon atom connected directly to the halogen

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45

beta position

carbon atoms connected to the alpha position

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46

SN2 reactions

  1. proceed via inversion of configuration because a nucleophile can inly attack from the back side

  2. they cannot be performed with tertiary alkyl halides

  3. will generally not occur if there are 3 subsitutents at a beta position

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47

E2 reactions

creation of alkenes

trans over cis is favored in the alkene

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48

Zaitsev product

favors the more substituted alkene

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49

Hoffman Product

favors the less substituted alkene

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50

Sn1

  1. loss of leaving group

  2. nucleophilic attack

favored by polar protic solvents

tertiary alkyl halides and allylic and benezylic halides

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51

Protic Solvents

contain a hydrogen atom connected directly to an electronegative atom

favored by Sn1 reactions

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52

polar aprotic solvents

lack a hydrogen connect directly to an electronegative atom

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53

addition reactions

the addition of two groups across a double bond

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54

Hydrohalogenation

the addition of H and X across a pi bond where X is a halogen

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55

Markovnikov additon

something will be placed at the more substituted position

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56

anti-Markovnikov additon

something will be placed in the less substituted position

in the presence of peroxides, addition of HBr

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57

Hydration

addition of water (H and OH ) across a double bond

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58

acid catalyzed hydration

addition of water in the presence of an acid which generally proceeds via Markovnikov addition

proceeds via a carbonation intermediate which is attacked by water to produce an oxoniuim ion followed by deprotonation

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59

Oxymercuration- demercuration

achieves hydration of an alkene without carbocation rearrangements

the reaction is believed to proceed via a bridged intermediate called a mercurinium ion

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60

Hydroboration Oxidation

can be used to achieve anti-mark addition of water across an alkene happens via syn addition

a borane is attacked by a pi bond triggering a simultaneous hydride shift

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61

Catalytic Hydrogenation

the addition of H2 across an alkene in the presence of a metal catalyst via syn addition

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62

Halogenation

involves the addition of X2 either Br2 or Cl2 across an alkene

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63

Bromination

proceeds via a bridged intermediate called a bromonium ion done via anti addition sn2 process

in the presence of water the product is bromohydrin or a chlorohydrin and the reaction is called halohydrin formation

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64

Dihydroxylation

reactions are characterized by the addition of OH and OH across an alkene

a two step procedure for an anti- involves the conversion of an alkene to an epoxide followed by acid catalyzed ring opening

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65

Ozonolysis

can be used to cleave a double bond and produce two carbonyl groups

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66

what Is a triple bond composed of

three seperate binds

one sigma bond

and 2 pi bonds

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67

Alkynes naming

the parent chain must include the triple bond within it

the triple bond should receive the lowest number possible

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68

dissolving metal reduction

will convert an internal alkyne into a trans alkene

this reaction involves an intermediate radical anion and fishhook arrows

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69

Acid-Catalyzed Hydration of alkynes

is catalyzed by mercuric sulfate (HgSO4) to produce an enroll that can’t be isolated because it is rapidly converted into a Ketone

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70

Tautomers

consitutional isomers that rapidly interconvert via the migration of a proton

an interconversion between and ketone and enol is catalyzed by trace amounts of acid or base

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71

Hydroboration- oxidation

of a terminal alkyne proceeds via an anti mark addition to produce an enol that can be converted in to a aldehyde via tautomerization which proceeds via a resonance stabilized anion called an enolate ion

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72

internal alkynes form what when they undergo oxidative cleavage

2 carboxylic acids

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73

Terminal Alkynes form what when they undergo oxidative cleavage

a Carboxylic acid and Carbon dioxide

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74

Which Radicals are resonance stabilized

Allylic and benzylic radicals

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75

Radical Mechanism

  1. Homolytic Cleavage

  2. Addition to a pi bond

  3. hydrogen abstraction

  4. Halogen Abstraction

  5. Elimination

  6. Coupling

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76

Radical Initiator

is compound with a weak bond that readily undergoes homolytic bond cleavage

Alkyl peroxides and acyl peroxides

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77

Radical inhibitor

is a compound that prevents a chain process from either getting started or continuing

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78

Allylic Bromination

bromination occurs at the allylic position

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79

how can the position of a halogen be moved

by performing an elimination followed by addition

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80

how can the position of a Pi bond be move

by performing an addition followed by an elimination

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81

how can a alkane be functionalized

via a radical bromination followed by elimination to give an alkene

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82

if a carbon skeleton increases

bond forming Is required

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83

If a carbon skeleton decreases

bond breaking , bond cleavage is required

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84

Constructive interference of Waves results in

a covalent bond

a wave with larger amplitude

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85

Destructive interference of waves results in

formation of a node

cancellation of both waves

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86

Straight line alkanes have a higher boiling point than

branched alkanes

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87

Electronegativity increases

to the right of the periodic table and up the periodic table

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88

the more hydrogens attached the higher the

Boiling point

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89

when an acid loses a proton , it always becomes a

conjugate base

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90

Delocalized lone pair

electrons can move and participate In resonance

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91

Atropisomers

a pair of chiral compounds that lack a chiral center

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92

which of the following compound is least acidic

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93

which of the following solvents would be the best for an Sn2 Reaction

acetonitrile

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94

which of the following would be classified as a bulky base

Diisopropylamine

t-Buok

Tea

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95

An __ Solvent such as __, would be most useful in an Sn2 Reaction

Aprotic and acetone

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96

In an E2 reaction, the use of a small base result in the ___. product , characterized as the

Zaitzev

Most substituted

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97

Stereochemistry in an Sn2 Reaction always results in

inversion of stereochemistry at the alpha carbon

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98

most stable radical

allylic

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99

if doubling the concentration of one reactant doubles the rate of reaction, but doubling the other reactant provides no impact on the reaction , which order of kinetics is it

first order

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100

Transition States

a high energy representation of a molecule that is not isolable

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