Organic Chemistry

studied byStudied by 78 people
4.7(6)
get a hint
hint

Alkanes

1 / 160

encourage image

There's no tags or description

Looks like no one added any tags here yet for you.

Studying Progress

0%
New cards
161
Still learning
0
Almost done
0
Mastered
0
161 Terms
1
New cards

Alkanes

<ul><li><p>First four alkanes are methane (CH4), Ethane (C2H6), Propane (C3H8), and Butane (C4H10)</p></li><li><p>single Bonded</p></li></ul>
  • First four alkanes are methane (CH4), Ethane (C2H6), Propane (C3H8), and Butane (C4H10)

  • single Bonded

<ul><li><p>First four alkanes are methane (CH4), Ethane (C2H6), Propane (C3H8), and Butane (C4H10)</p></li><li><p>single Bonded</p></li></ul>
New cards
2
New cards

Alkenes and Alkynes

<ul><li><p>Contain double and triple bonds respectively.</p></li></ul>
  • Contain double and triple bonds respectively.

<ul><li><p>Contain double and triple bonds respectively.</p></li></ul>
New cards
3
New cards

Alcohols

<ul><li><p>contain Hydroxyl group (OH)</p></li><li><p>suffix ol or hydroxy if a higher priority group is present</p></li><li><p>Diols contain two hydroxyl groups.</p></li></ul><ul><li><p>Geminal: 2 Hydroxyl groups on the same carbon</p></li><li><p>Vicinal: on adjacent carbons</p></li></ul>
  • contain Hydroxyl group (OH)

  • suffix ol or hydroxy if a higher priority group is present

  • Diols contain two hydroxyl groups.

  • Geminal: 2 Hydroxyl groups on the same carbon

  • Vicinal: on adjacent carbons

<ul><li><p>contain Hydroxyl group (OH)</p></li><li><p>suffix ol or hydroxy if a higher priority group is present</p></li><li><p>Diols contain two hydroxyl groups.</p></li></ul><ul><li><p>Geminal: 2 Hydroxyl groups on the same carbon</p></li><li><p>Vicinal: on adjacent carbons</p></li></ul>
New cards
4
New cards

Carbonyl group

knowt flashcard image
knowt flashcard image
New cards
5
New cards

Common Names of Aldehydes

<ul><li><p>suffix al</p></li><li><p>Common names include</p></li></ul><ul><li><p>formaldehyde for methanal (R = H)</p></li><li><p>Acetyldehyde for ethanal ( R = CH3)</p></li><li><p>Propionaldehyde for propanal (R = CH3CH2)</p></li></ul>
  • suffix al

  • Common names include

  • formaldehyde for methanal (R = H)

  • Acetyldehyde for ethanal ( R = CH3)

  • Propionaldehyde for propanal (R = CH3CH2)

<ul><li><p>suffix al</p></li><li><p>Common names include</p></li></ul><ul><li><p>formaldehyde for methanal (R = H)</p></li><li><p>Acetyldehyde for ethanal ( R = CH3)</p></li><li><p>Propionaldehyde for propanal (R = CH3CH2)</p></li></ul>
New cards
6
New cards

Aldehyde vs. Ketones Terminal group

  • An aldehyde has a terminal functional group due to the one hydrogen

  • Ketone has two alkyl groups so it's never a terminal group.

New cards
7
New cards

Naming cyclic Aldehydes

knowt flashcard image
knowt flashcard image
New cards
8
New cards

Aldehyde Nomenclature: Methanal

<p>Formaldehyde</p>

Formaldehyde

<p>Formaldehyde</p>
New cards
9
New cards

Aldehyde Nomenclature: Ethanal

<p>Acetaldehyde</p>

Acetaldehyde

<p>Acetaldehyde</p>
New cards
10
New cards

Aldehyde Nomenclature: Propanal

<p>Propionaldehyde</p>

Propionaldehyde

<p>Propionaldehyde</p>
New cards
11
New cards

Aldehyde Nomenclature: Butanal

<p>Butyraldehyde</p>

Butyraldehyde

<p>Butyraldehyde</p>
New cards
12
New cards

Aldehyde Nomenclature: Pentanal

<p>Valeraldehyde</p>

Valeraldehyde

<p>Valeraldehyde</p>
New cards
13
New cards

Naming Ketones: 2-propanone

<ul><li><p>Dimethyl ketone</p></li><li><p>Acetone</p></li></ul>
  • Dimethyl ketone

  • Acetone

<ul><li><p>Dimethyl ketone</p></li><li><p>Acetone</p></li></ul>
New cards
14
New cards

Naming Ketones: 2-butanone

<ul><li><p>ethylmethylketone</p></li></ul>
  • ethylmethylketone

<ul><li><p>ethylmethylketone</p></li></ul>
New cards
15
New cards

Naming Ketones: 3-oxobutanoic Acid

knowt flashcard image
knowt flashcard image
New cards
16
New cards

Naming Ketones: Cyclopentanone

knowt flashcard image
knowt flashcard image
New cards
17
New cards

Common Names for Ketones

<ul><li><p>suffix one</p></li><li><p>Acetone (dimethylketone; 2- propanone) ; smallest ketone; similar as the figure</p></li><li><p>2 pentanone (R= CH3CH2CH2)</p></li></ul>
  • suffix one

  • Acetone (dimethylketone; 2- propanone) ; smallest ketone; similar as the figure

  • 2 pentanone (R= CH3CH2CH2)

<ul><li><p>suffix one</p></li><li><p>Acetone (dimethylketone; 2- propanone) ; smallest ketone; similar as the figure</p></li><li><p>2 pentanone (R= CH3CH2CH2)</p></li></ul>
New cards
18
New cards

3-butene-2-one

<ul><li><p>Naming ketones</p></li><li><p>methylvinylketone</p></li></ul>
  • Naming ketones

  • methylvinylketone

<ul><li><p>Naming ketones</p></li><li><p>methylvinylketone</p></li></ul>
New cards
19
New cards

Carboxylic Acids and Derivatives

<ul><li><p>Contain both carbonyl group C=O and hydroxyl group (OH)</p></li><li><p>most oxidized group that appear on the MCAT</p></li><li><p>Suffix: Oic acid</p></li><li><p>Methanoic acid (Formic Acid)</p></li><li><p>Ethanoic acid (acetic acid)</p></li><li><p>Propanoic Acid (Propanoic Acid)</p></li></ul>
  • Contain both carbonyl group C=O and hydroxyl group (OH)

  • most oxidized group that appear on the MCAT

  • Suffix: Oic acid

  • Methanoic acid (Formic Acid)

  • Ethanoic acid (acetic acid)

  • Propanoic Acid (Propanoic Acid)

<ul><li><p>Contain both carbonyl group C=O and hydroxyl group (OH)</p></li><li><p>most oxidized group that appear on the MCAT</p></li><li><p>Suffix: Oic acid</p></li><li><p>Methanoic acid (Formic Acid)</p></li><li><p>Ethanoic acid (acetic acid)</p></li><li><p>Propanoic Acid (Propanoic Acid)</p></li></ul>
New cards
20
New cards

Ester

<ul><li><p>Carboxylic acid derivative</p></li><li><p>OH is replaced with OR, an alkoxy group</p></li></ul>
  • Carboxylic acid derivative

  • OH is replaced with OR, an alkoxy group

<ul><li><p>Carboxylic acid derivative</p></li><li><p>OH is replaced with OR, an alkoxy group</p></li></ul>
New cards
21
New cards

Amides

<ul><li><p>Carboxylic acid derivative</p></li><li><p>OH is replaced with an amino group</p></li></ul>
  • Carboxylic acid derivative

  • OH is replaced with an amino group

<ul><li><p>Carboxylic acid derivative</p></li><li><p>OH is replaced with an amino group</p></li></ul>
New cards
22
New cards

Anhydrides

<ul><li><p>Carboxylic acid derivative</p></li><li><p>formed by dehydration of 2 carboxylic acids</p></li></ul><ul><li><p>Symmetric = same acid</p></li><li><p>asymmetric = two different acids</p></li><li><p>cyclic = intramolecular reaction of a dicarboxylic acid</p></li></ul>
  • Carboxylic acid derivative

  • formed by dehydration of 2 carboxylic acids

  • Symmetric = same acid

  • asymmetric = two different acids

  • cyclic = intramolecular reaction of a dicarboxylic acid

<ul><li><p>Carboxylic acid derivative</p></li><li><p>formed by dehydration of 2 carboxylic acids</p></li></ul><ul><li><p>Symmetric = same acid</p></li><li><p>asymmetric = two different acids</p></li><li><p>cyclic = intramolecular reaction of a dicarboxylic acid</p></li></ul>
New cards
23
New cards

Summary of Functional Groups

Carboxylic acid > anhydride > Ester > Amide > Aldehyde > Ketone > Alcohol > alkene or alkyne > alkane

New cards
24
New cards

Structural Isomer

<ul><li><p>Share only a molecular formula</p></li><li><p>They have different physical and chemical properties</p></li></ul>
  • Share only a molecular formula

  • They have different physical and chemical properties

<ul><li><p>Share only a molecular formula</p></li><li><p>They have different physical and chemical properties</p></li></ul>
New cards
25
New cards

Conformational Isomer

<ul><li><p>Same molecule, differ in rotation around single pi bonds.</p></li></ul>
  • Same molecule, differ in rotation around single pi bonds.

<ul><li><p>Same molecule, differ in rotation around single pi bonds.</p></li></ul>
New cards
26
New cards

Newman's Projection

<ul><li><p>Anti staggered isomer has the lowest energy</p></li><li><p>Staggered isomer has the highest energy</p></li></ul>
  • Anti staggered isomer has the lowest energy

  • Staggered isomer has the highest energy

<ul><li><p>Anti staggered isomer has the lowest energy</p></li><li><p>Staggered isomer has the highest energy</p></li></ul>
New cards
27
New cards

Configurational Isomer

<ul><li><p>Can be interconverted only by breaking bonds.</p></li><li><p>consist of two categories:</p></li></ul><ul><li><p>Enantiomers: nonsuperimposable mirror image and thus have opposite stereochemistry at every chiral carbon.</p></li><li><p>Diasteromer: non- mirror image stereoisomers; differ at some but not all chiral centers. Ex) cis - trans isomers</p></li></ul>
  • Can be interconverted only by breaking bonds.

  • consist of two categories:

  • Enantiomers: nonsuperimposable mirror image and thus have opposite stereochemistry at every chiral carbon.

  • Diasteromer: non- mirror image stereoisomers; differ at some but not all chiral centers. Ex) cis - trans isomers

<ul><li><p>Can be interconverted only by breaking bonds.</p></li><li><p>consist of two categories:</p></li></ul><ul><li><p>Enantiomers: nonsuperimposable mirror image and thus have opposite stereochemistry at every chiral carbon.</p></li><li><p>Diasteromer: non- mirror image stereoisomers; differ at some but not all chiral centers. Ex) cis - trans isomers</p></li></ul>
New cards
28
New cards

Diastereomers

<ul><li><p>non- mirror image configurational isomer.</p></li><li><p>differ at some but not all chiral centers. Ex) cis - trans isomers</p></li></ul>
  • non- mirror image configurational isomer.

  • differ at some but not all chiral centers. Ex) cis - trans isomers

<ul><li><p>non- mirror image configurational isomer.</p></li><li><p>differ at some but not all chiral centers. Ex) cis - trans isomers</p></li></ul>
New cards
29
New cards

Enantiomer

<ul><li><p>Nearly identical physical properties and chemical properties</p></li><li><p>They rotate plane polarized light in opposite directions and react differently in chiral environment</p></li></ul>
  • Nearly identical physical properties and chemical properties

  • They rotate plane polarized light in opposite directions and react differently in chiral environment

<ul><li><p>Nearly identical physical properties and chemical properties</p></li><li><p>They rotate plane polarized light in opposite directions and react differently in chiral environment</p></li></ul>
New cards
30
New cards

Chiral center

<ul><li><p>4 different group attach to the central carbon</p></li><li><p>lack a plane of symmetry</p></li><li><p>not superimposable</p></li></ul>
  • 4 different group attach to the central carbon

  • lack a plane of symmetry

  • not superimposable

<ul><li><p>4 different group attach to the central carbon</p></li><li><p>lack a plane of symmetry</p></li><li><p>not superimposable</p></li></ul>
New cards
31
New cards

Achiral

<ul><li><p>Superimposable</p></li><li><p>line of symmetry</p></li></ul>
  • Superimposable

  • line of symmetry

<ul><li><p>Superimposable</p></li><li><p>line of symmetry</p></li></ul>
New cards
32
New cards

Racemix Mixture

  • Displays no optical activity

  • when both (+) and (-) enantiomers are present in equal concentrations.

  • Ex) A solution containing 2M (R)-2-butanol and 2 M (S)-2-butanol

New cards
33
New cards

Meso Compound

<ul><li><p>are essentially the molecular equivalent of a racemic mixture.</p></li><li><p>Racemix: when both (+) and (-) enantiomers are present in equal concentrations, no optical activity</p></li><li><p>Has a plane of symmetry = no optical activity</p></li><li><p>overall achiral ( mirror images that can be superimposed) and will not rotate plane polarized light.</p></li></ul>
  • are essentially the molecular equivalent of a racemic mixture.

  • Racemix: when both (+) and (-) enantiomers are present in equal concentrations, no optical activity

  • Has a plane of symmetry = no optical activity

  • overall achiral ( mirror images that can be superimposed) and will not rotate plane polarized light.

<ul><li><p>are essentially the molecular equivalent of a racemic mixture.</p></li><li><p>Racemix: when both (+) and (-) enantiomers are present in equal concentrations, no optical activity</p></li><li><p>Has a plane of symmetry = no optical activity</p></li><li><p>overall achiral ( mirror images that can be superimposed) and will not rotate plane polarized light.</p></li></ul>
New cards
34
New cards

(E) and (Z) Designations of Alkenes

<ul><li><p>Z : same side</p></li><li><p>E: Opposite side</p></li><li><p>used for compounds with polysubstituded double bonds.</p></li><li><p>Part of relative configuration</p></li></ul>
  • Z : same side

  • E: Opposite side

  • used for compounds with polysubstituded double bonds.

  • Part of relative configuration

<ul><li><p>Z : same side</p></li><li><p>E: Opposite side</p></li><li><p>used for compounds with polysubstituded double bonds.</p></li><li><p>Part of relative configuration</p></li></ul>
New cards
35
New cards

(R) and (S) Nomenclature

<ul><li><p>Used for chiral (stereogenic: 4 different groups bound to it in a non superimposable image) centers in molecules.</p></li><li><p>(R) rotates to the right; clockwise</p></li><li><p>(S) rotates to the left; counterclockwise</p></li><li><p>Part of relative configuration</p></li></ul>
  • Used for chiral (stereogenic: 4 different groups bound to it in a non superimposable image) centers in molecules.

  • (R) rotates to the right; clockwise

  • (S) rotates to the left; counterclockwise

  • Part of relative configuration

<ul><li><p>Used for chiral (stereogenic: 4 different groups bound to it in a non superimposable image) centers in molecules.</p></li><li><p>(R) rotates to the right; clockwise</p></li><li><p>(S) rotates to the left; counterclockwise</p></li><li><p>Part of relative configuration</p></li></ul>
New cards
36
New cards

Maximum number of stereoisomer

knowt flashcard image
knowt flashcard image
New cards
37
New cards

Equation for specific rotation

knowt flashcard image
knowt flashcard image
New cards
38
New cards

Single Bonds

<ul><li><p>Sigma bonds, contains two electrons.</p></li></ul><ul><li><p>Permit free rotation</p></li></ul>
  • Sigma bonds, contains two electrons.

  • Permit free rotation

<ul><li><p>Sigma bonds, contains two electrons.</p></li></ul><ul><li><p>Permit free rotation</p></li></ul>
New cards
39
New cards

Double Bonds

  • Contain one sigma bond and one pi bond.

  • Pi bonds are created by sharing of electrons between two unhybridized p-orbitals that align side by side.

  • Pi bonds do not permit rotations

New cards
40
New cards

Triple Bonds

  • Contain one sigma bond and two pi bonds.

  • Pi bonds do not permit rotations

New cards
41
New cards

Lewis Acid

<ul><li><p>Electron Acceptor in the formation of a covalent bond.</p></li><li><p>Tend to be electrophile</p></li><li><p>Vacant p-orbitals into which they can accept an electron pair.</p></li><li><p>Positively polarized atoms.</p></li></ul>
  • Electron Acceptor in the formation of a covalent bond.

  • Tend to be electrophile

  • Vacant p-orbitals into which they can accept an electron pair.

  • Positively polarized atoms.

<ul><li><p>Electron Acceptor in the formation of a covalent bond.</p></li><li><p>Tend to be electrophile</p></li><li><p>Vacant p-orbitals into which they can accept an electron pair.</p></li><li><p>Positively polarized atoms.</p></li></ul>
New cards
42
New cards

Lewis Base

<ul><li><p>Electron Donor in the formation of a covalent bond.</p></li><li><p>Nucleophile</p></li><li><p>Lone pair of electrons that can be donated, often anions; carrying a negative charge</p></li></ul>
  • Electron Donor in the formation of a covalent bond.

  • Nucleophile

  • Lone pair of electrons that can be donated, often anions; carrying a negative charge

<ul><li><p>Electron Donor in the formation of a covalent bond.</p></li><li><p>Nucleophile</p></li><li><p>Lone pair of electrons that can be donated, often anions; carrying a negative charge</p></li></ul>
New cards
43
New cards

Bronsted Lowry Acid

<ul><li><p>Proton Donor</p></li></ul>
  • Proton Donor

<ul><li><p>Proton Donor</p></li></ul>
New cards
44
New cards

Bronsted Lowry Base

<p>Proton Acceptor</p>

Proton Acceptor

<p>Proton Acceptor</p>
New cards
45
New cards

Amphoteric

<p>Ex) water can act as an acid by donating a proton or a base by accepting a proton .</p>

Ex) water can act as an acid by donating a proton or a base by accepting a proton .

<p>Ex) water can act as an acid by donating a proton or a base by accepting a proton .</p>
New cards
46
New cards

Acid Dissociation constant, Ka

<ul><li><p>Measures the strength of an acid in a solution</p></li><li><p>pKa can be calculated as -log Ka</p></li></ul><ul><li><p>smaller pKa = stronger the acid = below -2</p></li><li><p>Weak organic acids have a pKa between -2 and 20.</p></li></ul>
  • Measures the strength of an acid in a solution

  • pKa can be calculated as -log Ka

  • smaller pKa = stronger the acid = below -2

  • Weak organic acids have a pKa between -2 and 20.

<ul><li><p>Measures the strength of an acid in a solution</p></li><li><p>pKa can be calculated as -log Ka</p></li></ul><ul><li><p>smaller pKa = stronger the acid = below -2</p></li><li><p>Weak organic acids have a pKa between -2 and 20.</p></li></ul>
New cards
47
New cards

pKa

<ul><li><p>lower pKa = stronger Acid = below -2</p></li></ul><ul><li><p>-2 to 20 pKa is considered Weak Acid</p></li></ul><ul><li><p>Larger pKa = More Basic</p></li></ul>
  • lower pKa = stronger Acid = below -2

  • -2 to 20 pKa is considered Weak Acid

  • Larger pKa = More Basic

<ul><li><p>lower pKa = stronger Acid = below -2</p></li></ul><ul><li><p>-2 to 20 pKa is considered Weak Acid</p></li></ul><ul><li><p>Larger pKa = More Basic</p></li></ul>
New cards
48
New cards

An Acid-Base reaction will proceed when ...

The acid and Base react to form conjugate products that are weaker than the reactants.

New cards
49
New cards

Nucleophiles

<ul><li><p>Electron Donor; Good Bases</p></li><li><p>Tend to have lone pairs or pi bonds that cane be used to form covalent bonds to electrophiles ( electron acceptors)</p></li><li><p>(CHON) with a minus sign or lone pairs</p></li><li><p>Nucleophile strength is based on relative rates of reaction with a common electrophile; therefore, kinetic property.</p></li></ul>
  • Electron Donor; Good Bases

  • Tend to have lone pairs or pi bonds that cane be used to form covalent bonds to electrophiles ( electron acceptors)

  • (CHON) with a minus sign or lone pairs

  • Nucleophile strength is based on relative rates of reaction with a common electrophile; therefore, kinetic property.

<ul><li><p>Electron Donor; Good Bases</p></li><li><p>Tend to have lone pairs or pi bonds that cane be used to form covalent bonds to electrophiles ( electron acceptors)</p></li><li><p>(CHON) with a minus sign or lone pairs</p></li><li><p>Nucleophile strength is based on relative rates of reaction with a common electrophile; therefore, kinetic property.</p></li></ul>
New cards
50
New cards

Nucleophilicity is determined by 4 major factors:

<ul><li><p>Charge: Increases with increasing electron density (more negative charge)</p></li><li><p>Electronegativity: Decreases as electronegativity increases because these atoms are less likely to share electron density</p></li><li><p>Steric Hindrance: Bulkier molecule = less nucleophilic</p></li><li><p>Solvent: Protic solvents can hinder nucleophilicity by protonating the nucleophile or through hydrogen bonding.</p></li></ul>
  • Charge: Increases with increasing electron density (more negative charge)

  • Electronegativity: Decreases as electronegativity increases because these atoms are less likely to share electron density

  • Steric Hindrance: Bulkier molecule = less nucleophilic

  • Solvent: Protic solvents can hinder nucleophilicity by protonating the nucleophile or through hydrogen bonding.

<ul><li><p>Charge: Increases with increasing electron density (more negative charge)</p></li><li><p>Electronegativity: Decreases as electronegativity increases because these atoms are less likely to share electron density</p></li><li><p>Steric Hindrance: Bulkier molecule = less nucleophilic</p></li><li><p>Solvent: Protic solvents can hinder nucleophilicity by protonating the nucleophile or through hydrogen bonding.</p></li></ul>
New cards
51
New cards

Nucleophile in protic and aprotic solvents

<p>Protic: - I- &gt; Br- &gt; Cl- &gt; F Aprotic: F- &gt; Cl- &gt; Br-&gt; I-</p>

Protic: - I- > Br- > Cl- > F Aprotic: F- > Cl- > Br-> I-

<p>Protic: - I- &gt; Br- &gt; Cl- &gt; F Aprotic: F- &gt; Cl- &gt; Br-&gt; I-</p>
New cards
52
New cards

Strong Acids

knowt flashcard image
knowt flashcard image
New cards
53
New cards

Strong Base

knowt flashcard image
knowt flashcard image
New cards
54
New cards

Carboxylic Acid Derivatives

<ul><li><p>Often ranked by electrophilicity.</p></li><li><p>Anhydrides are the most reactive according to Kaplan.</p></li><li><p>Higher reactivity can form derivatives of lower reactivity but not vice versa.</p></li></ul>
  • Often ranked by electrophilicity.

  • Anhydrides are the most reactive according to Kaplan.

  • Higher reactivity can form derivatives of lower reactivity but not vice versa.

<ul><li><p>Often ranked by electrophilicity.</p></li><li><p>Anhydrides are the most reactive according to Kaplan.</p></li><li><p>Higher reactivity can form derivatives of lower reactivity but not vice versa.</p></li></ul>
New cards
55
New cards

Heterolytic Reactions

  • A bond is broken and both electrons are given to one of the two products.

  • The best leaving group is able to stabilize the extra electrons.

  • Weak bases (conjugate bases of strong acids such as I-, Br-, and Cl-) make good leaving groups

New cards
56
New cards

Mechanism of SN1 Reaction

<ol><li><p>rate-limiting step in which the leaving group leaves, generating a positively charge carbocation.</p></li><li><p>The nucleophile attacks the carbocation resulting in the substitution product.</p></li><li><p>Product will usually be a racemic mixture.</p></li><li><p>rate = k [R-L] ; [R-L] is an alkyl group containing a leaving group</p></li></ol>
  1. rate-limiting step in which the leaving group leaves, generating a positively charge carbocation.

  2. The nucleophile attacks the carbocation resulting in the substitution product.

  3. Product will usually be a racemic mixture.

  4. rate = k [R-L] ; [R-L] is an alkyl group containing a leaving group

<ol><li><p>rate-limiting step in which the leaving group leaves, generating a positively charge carbocation.</p></li><li><p>The nucleophile attacks the carbocation resulting in the substitution product.</p></li><li><p>Product will usually be a racemic mixture.</p></li><li><p>rate = k [R-L] ; [R-L] is an alkyl group containing a leaving group</p></li></ol>
New cards
57
New cards

Mechanism of SN2 Reaction

<ul><li><p>Contains only one step</p></li></ul><ol><li><p>Nucleophile (Backside attack; must be strong and substrate cannot be statically hindered) attacks the compound at the same time as the leaving group leaves</p></li><li><p>Substrate will often be alkyl halides, Tosylate, or mesylate</p></li><li><p>Rate = k [Nu:] [R-L]; [R-L] is an alkyl group containing a leaving group</p></li><li><p>Inversion of relative configuration will correspond to change in absolute configuration from (R) to (S) or vice versa.</p></li></ol>
  • Contains only one step

  1. Nucleophile (Backside attack; must be strong and substrate cannot be statically hindered) attacks the compound at the same time as the leaving group leaves

  2. Substrate will often be alkyl halides, Tosylate, or mesylate

  3. Rate = k [Nu:] [R-L]; [R-L] is an alkyl group containing a leaving group

  4. Inversion of relative configuration will correspond to change in absolute configuration from (R) to (S) or vice versa.

<ul><li><p>Contains only one step</p></li></ul><ol><li><p>Nucleophile (Backside attack; must be strong and substrate cannot be statically hindered) attacks the compound at the same time as the leaving group leaves</p></li><li><p>Substrate will often be alkyl halides, Tosylate, or mesylate</p></li><li><p>Rate = k [Nu:] [R-L]; [R-L] is an alkyl group containing a leaving group</p></li><li><p>Inversion of relative configuration will correspond to change in absolute configuration from (R) to (S) or vice versa.</p></li></ol>
New cards
58
New cards

How do the definitions of nucleophile and electrophile differ from those of Lewis Acids and Lewis Base?

  • Nucleophilicity and electrophilicity are based on relative rates of reactions therefore are kinetic properties.

  • Acidity and Basicity are measured by the position of equilibrium in a protonation or deprotonation reaction and are therefore thermodynamic properties.

New cards
59
New cards

How must the nucleophile and leaving group be related in order substitution reaction to proceed?

  • It will proceed when the nucleophile is a strong base (more reactive) than the leaving group.

  • Acid catalyst is required if the leaving group is a hydroxide ( bad leaving group) so it can get protonated to water (good leaving group) .

New cards
60
New cards

What trends increase electrophilicity?

  • Greater positive charge increases electrophilicity, and better leaving groups increase it by making the reaction to proceed.

New cards
61
New cards

What are some features of good leaving groups?

  • Good leaving groups can stabilize the extra electrons that result from heterolysis.

  • Weak bases (conjugate bases of strong acids such as I-, Br-, and Cl-) are good leaving groups.

  • Resonance stabilization also improve leaving groups

New cards
62
New cards

Oxidation State Order of Increase

  • Carboxylic Acid > Aldehydes, Ketones, and imines, which in turn are more oxidized than alcohols, alkyl halides, and amines.

  • Oxidation increases as the number of bonds to oxygen increases or other heteroatom (atoms besides carbon and oxygen)

New cards
63
New cards

Oxidizing Agents and Reactions

<ul><li><p>Accepts an electron from another species.</p></li><li><p>High Affinity for electrons such as O2, O3, and Cl2 or unusually high oxidation states (like Mn7+ in permanganate, MnO4-, and Cr6+ in chromate, CrO_4 ^2-)</p></li><li><p>Oxidation reactions: inc. # of bonds to oxygen</p></li><li><p>Oxidizing Agents: Metals bonded to large number of oxygen atoms.</p></li></ul>
  • Accepts an electron from another species.

  • High Affinity for electrons such as O2, O3, and Cl2 or unusually high oxidation states (like Mn7+ in permanganate, MnO4-, and Cr6+ in chromate, CrO_4 ^2-)

  • Oxidation reactions: inc. # of bonds to oxygen

  • Oxidizing Agents: Metals bonded to large number of oxygen atoms.

<ul><li><p>Accepts an electron from another species.</p></li><li><p>High Affinity for electrons such as O2, O3, and Cl2 or unusually high oxidation states (like Mn7+ in permanganate, MnO4-, and Cr6+ in chromate, CrO_4 ^2-)</p></li><li><p>Oxidation reactions: inc. # of bonds to oxygen</p></li><li><p>Oxidizing Agents: Metals bonded to large number of oxygen atoms.</p></li></ul>
New cards
64
New cards

Reduction of Carbon

  • Gains Electrons

  • When an atom that is more electronegative than carbon is replaced with less electronegative than carbon

  • Means increasing the number of bonds to Hydrogen and decreasing the number of bonds to carbons, nitrogen, oxygen and halides

New cards
65
New cards

Good Oxidizing Agents

<p>Metals bonded to a large number of Oxygen atoms.</p>

Metals bonded to a large number of Oxygen atoms.

<p>Metals bonded to a large number of Oxygen atoms.</p>
New cards
66
New cards

Good Reducing Agents

<p>Metals bonded to a large number of Hydrides.</p>

Metals bonded to a large number of Hydrides.

<p>Metals bonded to a large number of Hydrides.</p>
New cards
67
New cards

Bond Strength decreases down the periodic table

  • acidity increases.

  • Also Higher electronegative an atom, higher the acidity.

New cards
68
New cards

Oxidation of Primary Alcohol

<p>-Primary Alcohol Forms an aldehyde by Pyridinium Chlorochromate (PCC)</p><ul><li><p>Primary Alcohol is oxidized to a carboxylic acid by CrO3 (Jones Oxidation)</p></li></ul>

-Primary Alcohol Forms an aldehyde by Pyridinium Chlorochromate (PCC)

  • Primary Alcohol is oxidized to a carboxylic acid by CrO3 (Jones Oxidation)

<p>-Primary Alcohol Forms an aldehyde by Pyridinium Chlorochromate (PCC)</p><ul><li><p>Primary Alcohol is oxidized to a carboxylic acid by CrO3 (Jones Oxidation)</p></li></ul>
New cards
69
New cards

Oxidation of a Secondary Alcohol

<ul><li><p>Forms a Ketone by a Dichromate salt (Na_2Cr_2O_7 &amp; K_2Cr_2O_7)</p></li></ul>
  • Forms a Ketone by a Dichromate salt (Na_2Cr_2O_7 & K_2Cr_2O_7)

<ul><li><p>Forms a Ketone by a Dichromate salt (Na_2Cr_2O_7 &amp; K_2Cr_2O_7)</p></li></ul>
New cards
70
New cards

Protecting Groups of Acetals and Ketals

<ul><li><p>Acetals: primary carbon with 1 OR and an OH atom</p></li><li><p>Ketals: Secondary carbons with two OR groups.</p></li><li><p>Forms in the presence of a strong oxidizing agents.</p></li></ul>
  • Acetals: primary carbon with 1 OR and an OH atom

  • Ketals: Secondary carbons with two OR groups.

  • Forms in the presence of a strong oxidizing agents.

<ul><li><p>Acetals: primary carbon with 1 OR and an OH atom</p></li><li><p>Ketals: Secondary carbons with two OR groups.</p></li><li><p>Forms in the presence of a strong oxidizing agents.</p></li></ul>
New cards
71
New cards

Acetals and Ketal Formation

<ul><li><p>Acetals and Ketals are comparatively inert, are frequently used as protecting groups for carbonyl functionalities.</p></li><li><p>once a hemiacetal and hemiketal is formed, the hydroxyl group is protonated and released as a molecule of water; alcohol then attacks, forming an acetal or ketal.</p></li></ul>
  • Acetals and Ketals are comparatively inert, are frequently used as protecting groups for carbonyl functionalities.

  • once a hemiacetal and hemiketal is formed, the hydroxyl group is protonated and released as a molecule of water; alcohol then attacks, forming an acetal or ketal.

<ul><li><p>Acetals and Ketals are comparatively inert, are frequently used as protecting groups for carbonyl functionalities.</p></li><li><p>once a hemiacetal and hemiketal is formed, the hydroxyl group is protonated and released as a molecule of water; alcohol then attacks, forming an acetal or ketal.</p></li></ul>
New cards
72
New cards

Protecting Groups for alcohols

<ul><li><p>Make hydroxyl groups a better leaving groups for nucleophilic substitution</p></li><li><p>They can act as a protecting group when we do not want alcohol to react.</p></li></ul>
  • Make hydroxyl groups a better leaving groups for nucleophilic substitution

  • They can act as a protecting group when we do not want alcohol to react.

<ul><li><p>Make hydroxyl groups a better leaving groups for nucleophilic substitution</p></li><li><p>They can act as a protecting group when we do not want alcohol to react.</p></li></ul>
New cards
73
New cards

Quinone

<ul><li><p>Serve as electron acceptor biochemically; Electron Transport Chain in both photosynthesis and aerobic respiration.</p></li><li><p>Phylloquinone (Vitamin K1): important for photosynthesis and the carboxylation of some of the clotting factors in blood.</p></li><li><p>Menanquinones (Vitamin K2)</p></li></ul>
  • Serve as electron acceptor biochemically; Electron Transport Chain in both photosynthesis and aerobic respiration.

  • Phylloquinone (Vitamin K1): important for photosynthesis and the carboxylation of some of the clotting factors in blood.

  • Menanquinones (Vitamin K2)

<ul><li><p>Serve as electron acceptor biochemically; Electron Transport Chain in both photosynthesis and aerobic respiration.</p></li><li><p>Phylloquinone (Vitamin K1): important for photosynthesis and the carboxylation of some of the clotting factors in blood.</p></li><li><p>Menanquinones (Vitamin K2)</p></li></ul>
New cards
74
New cards

Three Examples of Hydroxyquinones

<ul><li><p>Share the same ring and carbonyl backbone as quinones but differ by the addition of one or more hydroxyl groups</p></li><li><p>a) Tetrahydroxybenzoquinone; b) 5-hyroxynaphthoquinone; c) 1,2-dihydroxyanthraquinone</p></li></ul>
  • Share the same ring and carbonyl backbone as quinones but differ by the addition of one or more hydroxyl groups

  • a) Tetrahydroxybenzoquinone; b) 5-hyroxynaphthoquinone; c) 1,2-dihydroxyanthraquinone

<ul><li><p>Share the same ring and carbonyl backbone as quinones but differ by the addition of one or more hydroxyl groups</p></li><li><p>a) Tetrahydroxybenzoquinone; b) 5-hyroxynaphthoquinone; c) 1,2-dihydroxyanthraquinone</p></li></ul>
New cards
75
New cards

Ubiquinone

<ul><li><p>Biologically active quinone (electron acceptor in photosynthesis and aerobic respiration)</p></li><li><p>Reduced to ubiquinol upon the acceptance of electrons.</p></li><li><p>Long alkyl chain = lipid soluble = act as an electron carrier within the phospholipid bilayer.</p></li></ul>
  • Biologically active quinone (electron acceptor in photosynthesis and aerobic respiration)

  • Reduced to ubiquinol upon the acceptance of electrons.

  • Long alkyl chain = lipid soluble = act as an electron carrier within the phospholipid bilayer.

<ul><li><p>Biologically active quinone (electron acceptor in photosynthesis and aerobic respiration)</p></li><li><p>Reduced to ubiquinol upon the acceptance of electrons.</p></li><li><p>Long alkyl chain = lipid soluble = act as an electron carrier within the phospholipid bilayer.</p></li></ul>
New cards
76
New cards

Hemiacetal Formation

<ul><li><p>The oxygen in the alcohol functions as a nucleophile, attacking the carbonyl carbon, and generating a hemiacetal.</p></li><li><p>Hemiacetals are unstable and the hydroxyl group is rapidly protonated and lost as water under acidic conditions, leaving behind a reactive carbocation.</p></li></ul>
  • The oxygen in the alcohol functions as a nucleophile, attacking the carbonyl carbon, and generating a hemiacetal.

  • Hemiacetals are unstable and the hydroxyl group is rapidly protonated and lost as water under acidic conditions, leaving behind a reactive carbocation.

<ul><li><p>The oxygen in the alcohol functions as a nucleophile, attacking the carbonyl carbon, and generating a hemiacetal.</p></li><li><p>Hemiacetals are unstable and the hydroxyl group is rapidly protonated and lost as water under acidic conditions, leaving behind a reactive carbocation.</p></li></ul>
New cards
77
New cards

Imine Formation

<ul><li><p>Ammonia (NH3) is added to the carbonyl, resulting in the elimination of water, and generating an imine.</p></li><li><p>Imine can undergo tautomerization and form enamine</p></li><li><p>Example of condensation reaction since a small molecule is lost during the formation of a bond between two molecules.</p></li></ul>
  • Ammonia (NH3) is added to the carbonyl, resulting in the elimination of water, and generating an imine.

  • Imine can undergo tautomerization and form enamine

  • Example of condensation reaction since a small molecule is lost during the formation of a bond between two molecules.

<ul><li><p>Ammonia (NH3) is added to the carbonyl, resulting in the elimination of water, and generating an imine.</p></li><li><p>Imine can undergo tautomerization and form enamine</p></li><li><p>Example of condensation reaction since a small molecule is lost during the formation of a bond between two molecules.</p></li></ul>
New cards
78
New cards

Imines and Enamines

knowt flashcard image
knowt flashcard image
New cards
79
New cards

Cyanohydrin or Hydrogen Cyanide (HCN)

<p>Cyanide functions as a nucleophile, attacking the carbonyl carbon and generating a cyanohydrin.</p>

Cyanide functions as a nucleophile, attacking the carbonyl carbon and generating a cyanohydrin.

<p>Cyanide functions as a nucleophile, attacking the carbonyl carbon and generating a cyanohydrin.</p>
New cards
80
New cards

Aldehyde oxidation

<ul><li><p>Also H2O2</p></li></ul>
  • Also H2O2

<ul><li><p>Also H2O2</p></li></ul>
New cards
81
New cards

Reduction by Hydride Reagents

<ul><li><p>Lithium aluminum hydride (LiAlH4)</p></li><li><p>Sodium borohydride (NaBH4)</p></li></ul>
  • Lithium aluminum hydride (LiAlH4)

  • Sodium borohydride (NaBH4)

<ul><li><p>Lithium aluminum hydride (LiAlH4)</p></li><li><p>Sodium borohydride (NaBH4)</p></li></ul>
New cards
82
New cards

Geminal Diol

  • A compound with two hydroxyl groups on the same carbon due to a hydration reaction, water adds to a carbonyl.

New cards
83
New cards

Tautomers

<ul><li><p>Two isomers, which differ in the placement of a proton and the double bond</p></li></ul>
  • Two isomers, which differ in the placement of a proton and the double bond

<ul><li><p>Two isomers, which differ in the placement of a proton and the double bond</p></li></ul>
New cards
84
New cards

Michael Addition

knowt flashcard image
knowt flashcard image
New cards

Explore top notes

note Note
studied byStudied by 5 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 1 person
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 11 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 10 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 4 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 8 people
Updated ... ago
5.0 Stars(2)
note Note
studied byStudied by 2 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 47701 people
Updated ... ago
4.9 Stars(537)

Explore top flashcards

flashcards Flashcard40 terms
studied byStudied by 25 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard51 terms
studied byStudied by 497 people
Updated ... ago
4.5 Stars(16)
flashcards Flashcard35 terms
studied byStudied by 12 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard121 terms
studied byStudied by 7 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard312 terms
studied byStudied by 6 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard155 terms
studied byStudied by 55 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard35 terms
studied byStudied by 7 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard52 terms
studied byStudied by 36 people
Updated ... ago
5.0 Stars(4)