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MCAT > Organic Chem > Flashcards

Organic Chem Flashcards

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MCAT flashcards
0
Q

Elimination reaction for alkyl halides

A

Page 809

  • E1/E2
  • leaving groups
  • order (for reaction rate)
  • 3,2 or 1 prime
  • stereochemistry
  • strong/weak base
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1
Q

Nucleophilic substitution of alkyl halides

A

Page 803

  • Sn1/Sn2
  • leaving group/nucleophile
  • order (for reaction rate)
  • 3,2 or 1 prime
  • stereochemistry
  • solvent effects
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2
Q

What stabilizes acidity of alcohols?

A

Page 814
Resonance
Steric hindrance
Electron withdrawal

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3
Q

Preparation of alcohols

A

Page 789 and 816

  • hydration of an alkene
  • hydroboration-oxidation of an alkene
  • reduction of aldehydes, ketones, and esters
  • gringard reagent with carbonyl compounds, aldehydes and ketones
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4
Q

Reduction of aldehyde

A

Page 816
Using NaBH4 or LiAlH4, ethanol and H3O+
Produces primary alcohol

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5
Q

Reduction of ketone

A

Page 816
Using NaBH4 or LiAlH4, ethanol and H3O+
Produces secondary alcohol

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6
Q

Reduction of carboxylic acid

A

Page 816
With reducing agent
Produces primary alcohol

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7
Q

Reduction of ester

A

Page816
With reducing agent
Produces primary alcohol

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8
Q

Carbonyl compound (formaldehyde) with gringard reagent

A

With GR, ether and H3O+

Makes primary alcohol

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9
Q

Aldehyde with gringard reagent

A

With ether and H3O+

Produces secondary alcohol

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10
Q

Ketone and gringard reagent

A

With GR and H3O+

Produces tertiary alcohol

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11
Q

Alcohol to alkyl halides using halides (in presence of acid catalyst)

A

Page 818

  • Sn1/Sn2 mechanisms
  • 3,2 and 1 prime
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12
Q

Reaction with halides to form alkyl halides from alcohol (under non-acidic conditions)

A

Using PBr3 (phosphorus tribromide) or SOCl3 (thionyl chloride)

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13
Q

Dehydration of alcohols

A

Page 819

  • acid catalyzed elimination
  • E1 elimination
  • forms alkenes
  • 3,2, and 1 prime
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14
Q

Primary alcohol oxidized with weak oxidizing agent (like PCC)

A

Page 820

Produces aldehyde

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15
Q

Primary alcohol oxidized with strong oxidizing agent (like KMnO4)

A

Page 820

Produces carboxylic acid

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16
Q

Oxidation of a secondary alcohol

A

Page 820

Produces a ketone

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17
Q

Oxidation of a tertiary alcohol

A

Does not occur… There are no alpha hydrogens to take!

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18
Q

Ozonolysis

A

Page 829

The process of cleaving alkenes with ozone

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19
Q

How to prepare aryl ketones

A

Via Friedel Crafts acylation

Page 831

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20
Q

Nucleophilic addition of aldehydes and ketones

A

Page 832

  • which are more susceptible?
  • why do a/k favour nucleophilic attack
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21
Q

How to form hemiacetals and hemiketals

A

Page 833

  • through nucleophilic addition of an alcohol
  • acid vs base catalyzation
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22
Q

Formation of acetals from hemiacetals

A

Page 835

  • catalyst
  • stable environments for acetals
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23
Q

Imine formation

A

Page 837
Adding amines to form imines
Uses acid catalyst
Acid must be at a specific ph of about 5 (not too strong or the initial amine will just be protonated and this useless in the process)

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24
Q

What is an enoliate ion?

A

Page 838
An aldehyde or ketone with one of it’s alpha hydrogens removed
It is a resonance structure and thus very stable

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25
Q

Aldol reaction

A

Page 838

  • Base catalyzed
  • 2 aldehydes react with an enolate ion (as an intermediate) to form a dimer (Aldol) which is essentially an alcohol with an aldehyde
  • 3 steps
  • can be dehydrated (Aldol condensation) to form enone which is an unsaturated aldehyde
  • how do ketones fair in this reaction?
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26
Q

Wittig reaction

A

Page 840

-reacting with an aldehyde or ketone with a phosphorus ylide to produce an alkene

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27
Q

Oxidation of aldehydes and ketones

A

Page 842

  • aldehydes undergo oxidation readily to produce carboxylic acids
  • ketones do not undergo oxidation because the carbonyl carbon isn’t bound to hydrogen, which must be abstracted during the oxidation reaction
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28
Q

2 main types of carbohydrates ?

A

Page 899
Simple and complex carbs
Subdivided into aldoses and ketoses

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29
Q

D and L assignments for carbohydrates

A

Page 901
Only for those with chiral centers
how does it correspond to r/s configuration. For glyceraldehyde?
How does it correspond to +/- ?

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30
Q

Glyceraldehyde/aldotriose

A

Page 901

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31
Q

Dihydroxyacetone/ketotriose

A

Page 901

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32
Q

In nature, how do most monosaccharides appear?

A

In their D form

Note that for a 5 carbon sugar, D-glucose is of greatest biological importance

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33
Q

How to know how many stereoisomers & D/L pairs a carbohydrate has

A

n=2^x-2

Half of that is the number of pairs of D/L enatiomers

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34
Q

How do aldoses and ketoses form ring structures?

A

Page 907

  • anomeric carbon
  • pyranose/glucopyranose
  • furanose
  • how to number the carbons
  • what is the most oxidized carbon
  • anomers (alpha and beta)
  • chair form
  • mutarotation
  • thermodynamically favored form
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35
Q

What are disaccharides?

A

Page 909

  • type of linkage
  • alpha/beta linkage
  • how to make sucrose
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36
Q

What is starch?

A

Page 910

  • types of linkages
  • what happens on heating
  • why it’s biologically significant
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37
Q

What is glycogen?

A

Page 911

  • how it differs from amylopectin
  • how many glucose units is it
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38
Q

Describe Bendict’s test for reducing sugars

A

Page 911

-what will have +/- results?

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39
Q

Describe cellulose

A

Page 912

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40
Q

Describe extraction

A

Page 917

  • what 3 molecules can be altered so they dissolve in the aqueous layer
  • acid/base strength for extraction
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41
Q

Polarity of organic substances

A

Non-polar

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42
Q

Describe the recrystalization process and how to select recrytalization solvents. How this compares to precipitation.

A

Page 920

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43
Q

Describe the distillation process

A

Page 921

-different types and temperatures at which they occur

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44
Q

Describe chromatography

A

Page 923

  • 3 types
  • stationary vs mobile phase
  • Rf value
  • relative polarities of organic functional groups
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45
Q

Describe electrophoresis

A

Page 925

What is is commonly used for?

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46
Q

Describe mass spectroscopy

A

Page 926

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47
Q

Describe UV spectroscopy

A

Page 927

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48
Q

Infrared spectroscopy

A

Page 928

What is a wave number

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49
Q

IR for C=O

A

1690-1729cm-1

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50
Q

IR for O-H

A

3600-3200cm-1

51
Q

IR for C=C

A

~1650 cm-1

52
Q

IR for C triple bonded to C and C triple bonded to N

A

2250-2100cm-1

53
Q

IR of C-H (alkane)

A

2960-2850cm-1

54
Q

Describe nuclear magnetic resonance spectroscopy

A

Page 930

55
Q

Describe the orbital hybridization proces for sp, sp2 and sp3 orbitals

A

Page 731

How are double/triple/single bonds formed

56
Q

Describe a dipole moment

A

Page 738

57
Q

Describe hydrogen bonding

A

Page 741

Which molecules must the H be bound to?

58
Q

Describe resonance structures

A

Page 742

Do they alternate between forms?

59
Q

Draw the table with the different types of isomers

A

Page 751

Which ones are optically active/have different chemical properties?

60
Q

Describe a structural isomer

A

Page 752

61
Q

Describe a chiral molecule

A

Page 753

If there is only 1 chiral center present, it must be chiral but if there is more than one, it may or may not be chiral

62
Q

What is deuterium?

A

An isotope of hydrogen, heavier than hydrogen itself. (atomic mass is 2)

63
Q

Describe how to assign R/S configurations

A

Page 754

64
Q

How to determine d/l for plane polarized light

A

Page 757

65
Q

Describe a racemic mixture

A

Page 759

66
Q

Formula for maximum number of stereoisomers?

A

2^n

n is number of chiral centers

67
Q

Describe diastereomers

A

Page 760

Optical activity?

68
Q

What’s an epimer?

A

Page 761

All epimers are diastereomers but not all diastereomers are epimers

69
Q

Know how many stereoisomers/diastereomers/enatiomers a given substance has

A

Page 762

70
Q

Describe a meso compound

A

Page 763
Plane of symmetry
Not optically active bc not chiral

71
Q

Describe cis/trans diastereomers and e/z notation

A

Page 766

72
Q

Draw the chart describing hydrocarbons

A

Page 771

73
Q

How to name alkanes

A

Page 772-776

74
Q

Physical properties of alkanes

A

Page 776

  • solubility
  • melting/boiling point
  • state (solid liquid or gas)
  • chart relating sa/forces/density/branching
75
Q

Halogenation of the alkanes

A

Page 778

  • selectivity (regiosective high vs low- which halogens are which)
  • formula for less regioselective species
76
Q

Combustion of alkanes

A

Page 782

77
Q

Pyrolysis of alkanes

A

Page 783

78
Q

Know how to name alkenes

A

Page 783

79
Q

Electrophilic addition of alkyl halides for alkenes

A

Page 785

  • Markovnikov vs anti Markovnikov
  • steps
  • hydride/methyl shifts
  • when does anti-M occur? (p 789)
80
Q

Hydration of alkenes

A

Page 789

81
Q

Hydroboration-oxidation of alkenes

A

Page 790

-syn or anti addition?

82
Q

Halogen addition of alkenes

A

Page 791

-anti or syn addition

83
Q

Describe a benzene ring

A

Page 793

  • it’s considered aromatic if…
  • stability
  • possible substituents
84
Q

How to name places on a substituted benzene ring

A

Page 794

85
Q

Electrophilic aromatic substitution of a benzene ring

A

Page 794

  • 3 types
  • electron withdrawing/releasing effects
  • meta/ortho,para directors
86
Q

Naming carboxylic acids

A

Page 847

87
Q

Hydrogen bonding/bp/solubility of carboxylic acids

A

Page 849

88
Q

Acidity of carboxylic acids

A

Page 850
Wrt alcohols and why
Wrt alpha carbon substituents

89
Q

Preparation of carboxylic acids

A

Page 853
Oxidation and best oxidizing agent
Carboxylation of gringard reagents

90
Q

Reduction of carboxylic acid

A

Page 855 & 866

Yields primary alcohols

91
Q

Decarboxylation of carboxylic acids

A

Page 855

Speed

92
Q

Carboxylic acid to acid chlorides

A

Page 857

93
Q

Carboxylic acid to acid anhydrides

A

Page 857
With pyridine present
Cyclic anhydrides

94
Q

Carboxylic acid to ester

A

Page 858

95
Q

Carboxylic acid to amine

A

Page 858

96
Q

Acid chlorides to amides

A

Page 859

97
Q

Acid anhydrides to amides

A

Page 859

Imide formation

98
Q

Esters to amides

A

Page 859

99
Q

What is an acyl transfer?

A

Page 861

How reactive each is

100
Q

Acid chlorides to carboxylic acids

A

Page 861

101
Q

Acid chlorides to esters

A

Page 861

102
Q

Acid anhydrides to esters

A

Page 861

103
Q

Acid catalyzed hydrolysis of esters

A

Page 863

104
Q

Base promoted hydrolysis of esters

A

Page 864

105
Q

Transesterificstion

A

Page 864

106
Q

Esters to alcohols

A

Page 864

107
Q

Amides to carboxylic acids

A

Page 865

108
Q

What is a micelle?

A

Page 864

109
Q

Describe amines and ammonia

A

Page 873

110
Q

What is a quaternary ammonium salt?

A

Page 873

111
Q

What is an amino group/cyclic amine?

A

Page 874

112
Q

How to name amines

A

Page 875

113
Q

Physical properties of amines

Bp, water solubility, hydrogen bonding (for primary, secondary and tertiary amines)

A

Page 875

114
Q

Describe the basicity of amines

A

Page 877

115
Q

Describe what an amino acid looks like

A

Page 879

116
Q

Describe the charity of amino acids

A

Page 879

117
Q

L an D classification of amino acids

A

Page 881

118
Q

How to classify acidic or basic amino acids (and exceptions)

A

Page 882

Exceptions asparagine and glutamine

119
Q

Explain the sulfur containing amino acids

A

Page 883

120
Q

What is a zwitterion?

Define the isoelectric point

A

Page 884

121
Q

What is an atmospheric species?

A

Page 887

122
Q

Is an amino acid an acid or base?

A

Page 887

Both depending on ambient pH

123
Q

Describe what happens if an amino acid is both protonated or both deprotonated (wrt raise/lowered pH)

A

Page 887

124
Q

How to form and break peptide bonds

A

Page 890

125
Q

Describe the words dipeptide, polypeptide, protein, and amino acid residue

A

Page 890

126
Q

Describe the 4 structures of proteins

  • how they are named
  • types
  • types of bonds
A

Page 891

MCAT (6 decks)

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