Organic Chem Flashcards
(127 cards)
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
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
2
Q
What stabilizes acidity of alcohols?
A
Page 814
Resonance
Steric hindrance
Electron withdrawal
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
4
Q
Reduction of aldehyde
A
Page 816
Using NaBH4 or LiAlH4, ethanol and H3O+
Produces primary alcohol
5
Q
Reduction of ketone
A
Page 816
Using NaBH4 or LiAlH4, ethanol and H3O+
Produces secondary alcohol
6
Q
Reduction of carboxylic acid
A
Page 816
With reducing agent
Produces primary alcohol
7
Q
Reduction of ester
A
Page816
With reducing agent
Produces primary alcohol
8
Q
Carbonyl compound (formaldehyde) with gringard reagent
A
With GR, ether and H3O+
Makes primary alcohol
9
Q
Aldehyde with gringard reagent
A
With ether and H3O+
Produces secondary alcohol
10
Q
Ketone and gringard reagent
A
With GR and H3O+
Produces tertiary alcohol
11
Q
Alcohol to alkyl halides using halides (in presence of acid catalyst)
A
Page 818
- Sn1/Sn2 mechanisms
- 3,2 and 1 prime
12
Q
Reaction with halides to form alkyl halides from alcohol (under non-acidic conditions)
A
Using PBr3 (phosphorus tribromide) or SOCl3 (thionyl chloride)
13
Q
Dehydration of alcohols
A
Page 819
- acid catalyzed elimination
- E1 elimination
- forms alkenes
- 3,2, and 1 prime
14
Q
Primary alcohol oxidized with weak oxidizing agent (like PCC)
A
Page 820
Produces aldehyde
15
Q
Primary alcohol oxidized with strong oxidizing agent (like KMnO4)
A
Page 820
Produces carboxylic acid
16
Q
Oxidation of a secondary alcohol
A
Page 820
Produces a ketone
17
Q
Oxidation of a tertiary alcohol
A
Does not occur… There are no alpha hydrogens to take!
18
Q
Ozonolysis
A
Page 829
The process of cleaving alkenes with ozone
19
Q
How to prepare aryl ketones
A
Via Friedel Crafts acylation
Page 831
20
Q
Nucleophilic addition of aldehydes and ketones
A
Page 832
- which are more susceptible?
- why do a/k favour nucleophilic attack
21
Q
How to form hemiacetals and hemiketals
A
Page 833
- through nucleophilic addition of an alcohol
- acid vs base catalyzation
22
Q
Formation of acetals from hemiacetals
A
Page 835
- catalyst
- stable environments for acetals
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)
24
What is an enoliate ion?
Page 838
An aldehyde or ketone with one of it's alpha hydrogens removed
It is a resonance structure and thus very stable
25
Aldol reaction
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?
26
Wittig reaction
Page 840
| -reacting with an aldehyde or ketone with a phosphorus ylide to produce an alkene
27
Oxidation of aldehydes and ketones
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
28
2 main types of carbohydrates ?
Page 899
Simple and complex carbs
Subdivided into aldoses and ketoses
29
D and L assignments for carbohydrates
Page 901
Only for those with chiral centers
how does it correspond to r/s configuration. For glyceraldehyde?
How does it correspond to +/- ?
30
Glyceraldehyde/aldotriose
Page 901
31
Dihydroxyacetone/ketotriose
Page 901
32
In nature, how do most monosaccharides appear?
In their D form
| Note that for a 5 carbon sugar, D-glucose is of greatest biological importance
33
How to know how many stereoisomers & D/L pairs a carbohydrate has
n=2^x-2
| Half of that is the number of pairs of D/L enatiomers
34
How do aldoses and ketoses form ring structures?
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
35
What are disaccharides?
Page 909
- type of linkage
- alpha/beta linkage
- how to make sucrose
36
What is starch?
Page 910
- types of linkages
- what happens on heating
- why it's biologically significant
37
What is glycogen?
Page 911
- how it differs from amylopectin
- how many glucose units is it
38
Describe Bendict's test for reducing sugars
Page 911
| -what will have +/- results?
39
Describe cellulose
Page 912
40
Describe extraction
Page 917
- what 3 molecules can be altered so they dissolve in the aqueous layer
- acid/base strength for extraction
41
Polarity of organic substances
Non-polar
42
Describe the recrystalization process and how to select recrytalization solvents. How this compares to precipitation.
Page 920
43
Describe the distillation process
Page 921
| -different types and temperatures at which they occur
44
Describe chromatography
Page 923
- 3 types
- stationary vs mobile phase
- Rf value
- relative polarities of organic functional groups
45
Describe electrophoresis
Page 925
| What is is commonly used for?
46
Describe mass spectroscopy
Page 926
47
Describe UV spectroscopy
Page 927
48
Infrared spectroscopy
Page 928
| What is a wave number
49
IR for C=O
1690-1729cm-1
50
IR for O-H
3600-3200cm-1
51
IR for C=C
~1650 cm-1
52
IR for C triple bonded to C and C triple bonded to N
2250-2100cm-1
53
IR of C-H (alkane)
2960-2850cm-1
54
Describe nuclear magnetic resonance spectroscopy
Page 930
55
Describe the orbital hybridization proces for sp, sp2 and sp3 orbitals
Page 731
| How are double/triple/single bonds formed
56
Describe a dipole moment
Page 738
57
Describe hydrogen bonding
Page 741
| Which molecules must the H be bound to?
58
Describe resonance structures
Page 742
| Do they alternate between forms?
59
Draw the table with the different types of isomers
Page 751
| Which ones are optically active/have different chemical properties?
60
Describe a structural isomer
Page 752
61
Describe a chiral molecule
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
What is deuterium?
An isotope of hydrogen, heavier than hydrogen itself. (atomic mass is 2)
63
Describe how to assign R/S configurations
Page 754
64
How to determine d/l for plane polarized light
Page 757
65
Describe a racemic mixture
Page 759
66
Formula for maximum number of stereoisomers?
2^n
| n is number of chiral centers
67
Describe diastereomers
Page 760
| Optical activity?
68
What's an epimer?
Page 761
| All epimers are diastereomers but not all diastereomers are epimers
69
Know how many stereoisomers/diastereomers/enatiomers a given substance has
Page 762
70
Describe a meso compound
Page 763
Plane of symmetry
Not optically active bc not chiral
71
Describe cis/trans diastereomers and e/z notation
Page 766
72
Draw the chart describing hydrocarbons
Page 771
73
How to name alkanes
Page 772-776
74
Physical properties of alkanes
Page 776
- solubility
- melting/boiling point
- state (solid liquid or gas)
- chart relating sa/forces/density/branching
75
Halogenation of the alkanes
Page 778
- selectivity (regiosective high vs low- which halogens are which)
- formula for less regioselective species
76
Combustion of alkanes
Page 782
77
Pyrolysis of alkanes
Page 783
78
Know how to name alkenes
Page 783
79
Electrophilic addition of alkyl halides for alkenes
Page 785
- Markovnikov vs anti Markovnikov
- steps
- hydride/methyl shifts
- when does anti-M occur? (p 789)
80
Hydration of alkenes
Page 789
81
Hydroboration-oxidation of alkenes
Page 790
| -syn or anti addition?
82
Halogen addition of alkenes
Page 791
| -anti or syn addition
83
Describe a benzene ring
Page 793
- it's considered aromatic if...
- stability
- possible substituents
84
How to name places on a substituted benzene ring
Page 794
85
Electrophilic aromatic substitution of a benzene ring
Page 794
- 3 types
- electron withdrawing/releasing effects
- meta/ortho,para directors
86
Naming carboxylic acids
Page 847
87
Hydrogen bonding/bp/solubility of carboxylic acids
Page 849
88
Acidity of carboxylic acids
Page 850
Wrt alcohols and why
Wrt alpha carbon substituents
89
Preparation of carboxylic acids
Page 853
Oxidation and best oxidizing agent
Carboxylation of gringard reagents
90
Reduction of carboxylic acid
Page 855 & 866
| Yields primary alcohols
91
Decarboxylation of carboxylic acids
Page 855
| Speed
92
Carboxylic acid to acid chlorides
Page 857
93
Carboxylic acid to acid anhydrides
Page 857
With pyridine present
Cyclic anhydrides
94
Carboxylic acid to ester
Page 858
95
Carboxylic acid to amine
Page 858
96
Acid chlorides to amides
Page 859
97
Acid anhydrides to amides
Page 859
| Imide formation
98
Esters to amides
Page 859
99
What is an acyl transfer?
Page 861
| How reactive each is
100
Acid chlorides to carboxylic acids
Page 861
101
Acid chlorides to esters
Page 861
102
Acid anhydrides to esters
Page 861
103
Acid catalyzed hydrolysis of esters
Page 863
104
Base promoted hydrolysis of esters
Page 864
105
Transesterificstion
Page 864
106
Esters to alcohols
Page 864
107
Amides to carboxylic acids
Page 865
108
What is a micelle?
Page 864
109
Describe amines and ammonia
Page 873
110
What is a quaternary ammonium salt?
Page 873
111
What is an amino group/cyclic amine?
Page 874
112
How to name amines
Page 875
113
Physical properties of amines
| Bp, water solubility, hydrogen bonding (for primary, secondary and tertiary amines)
Page 875
114
Describe the basicity of amines
Page 877
115
Describe what an amino acid looks like
Page 879
116
Describe the charity of amino acids
Page 879
117
L an D classification of amino acids
Page 881
118
How to classify acidic or basic amino acids (and exceptions)
Page 882
| Exceptions asparagine and glutamine
119
Explain the sulfur containing amino acids
Page 883
120
What is a zwitterion?
| Define the isoelectric point
Page 884
121
What is an atmospheric species?
Page 887
122
Is an amino acid an acid or base?
Page 887
| Both depending on ambient pH
123
Describe what happens if an amino acid is both protonated or both deprotonated (wrt raise/lowered pH)
Page 887
124
How to form and break peptide bonds
Page 890
125
Describe the words dipeptide, polypeptide, protein, and amino acid residue
Page 890
126
Describe the 4 structures of proteins
- how they are named
- types
- types of bonds
Page 891
