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Alle Oberthemen / Chemistry / MCAT

MCAT Orgo Rules and Properties (47 Karten)

Sag Danke
1
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Functional Group Prefixes and Suffixes
2
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Ketone and Aldehyde Properties
-positive alpha-carbon
-acidic beta-carbon
-elevation in BP from alkane due to dipole
-BP not up to alcohol due to no hydrogen bonding
-aldehydes more reactive than ketones. Why?
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Alcohol Properties
-hydrogen bonding (# hydroxyl groups)
-high boiling points
-weakly acidic (pKa = 10phenol to 16water)
-6-carbon rule = alcohols with C-chains > 6 are no longer soluble
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Criteria of Aromaticity
1. Huckel's Rule (4n+2)
2. Planar and cyclic
3. Every atom delocalized
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Alkene polarity
Trans alkenes have higher melting points (symmetrical) and lower boiling points (less likely to be polar).

SP3 carbons donate electrons to SP2 carbons - orbitals more s character, closer to nucleus, more stable.

Tags: physical properties
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Oxidation of a double bond
1. KMnO
     - mild conditions (vicinal diols)
     - extreme conditions (carboxylic acids)

2. Ozonolysis
     - mild conditions, reducing Zn/water environment (ketones/aldehydes)
     - extreme conditions, oxidizing environment

3. NaBH or LiAlH

4. Peroxyacetic acids = CHCOH or MCPBA (epoxide formation)

5. Hydroboration (NaBH, peroxide)
Tags: rxns
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How do you control for E2, versus SN2?
-bulky, stronger base
   (NOT -CN or -I or even -OH, but -OR)
-substrate steric hindrance
   (why? hydrogen removal rather than )
-HEAT

Key Points
bulky base = E2
heat = E2
3*C substrate = E2
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Chlorination energy diagram
9
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How do you find the reactivity of hydrogens?
Find the amount of product formed per hydrogen and compare.
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Hammond Postulate
Related species that are similar in energy are also similar in structure. The structure of the transition state resembles the structure of the closest stable species.

-transition state for endothermic rxns resembles the product, exothermic the reactant.
-bromination transition state is closest to product. Thus reactivity very closely related to end-product stability (i.e. stability=speed).
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Bromination energy diagram
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Physical properties of alkanes
*chain length; increase
   -bioling point
   -melting point
   -density

*branching; decrease
   -boiling point
   -density

*melting point and branching - determined by how symmetrical the molcule is; packing density. Easier to stack, more dense, higher melting point.
Tags: physical properties
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Factors affecting substitution
1. Basicity of Nu
       RO- > HO- > RCO > ROH > HO
2. Polarizability (size) of Nu
       CN- > I- > RO- > HO- > Br-
3. Solvent
      -protic = solvate the leaving group.
      -polar = solvate the intermediate.
4. Leaving group (base weakness)
5. Substrate (charge delocalization)
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Relative versus absolute configuration
Relative = experimentally determined, x-ray crystallography; always reversed in SN2 reactions (D/L; +/-).

Absolute = determined by priority group orientations; not necessarily reversed in SN2 reactions (R/S).
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SN1 reaction
-good leaving group
-stable substrate, bulky Nu.
-favored in polar, protic solvents
-two steps (two transition states)
-rate=k[RX] ; first order kinetics
-racemic products
-rate limiting step is the first step = formation of the carbocation.
16
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In free-radical halogenation, why is bromine more selective than chlorine?
1. Slower reaction
2. Transition state more dependent on product stability (endothermic)
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What is the difference between a transition state and an intermediate?
Intermediate = stable, relative minimum, stable species.
Transition state = theoretical, unstable, relative maximum, for mechanism solely.
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SN2 reactions
-Nu > leaving group
-favored in aprotic POLAR solvents
-r=k[Nu][RX] ; second-order kinetics
-reverse relative configuration
-no steric hindrance in substrate, small Nu.
-trigonal bipyramidal transition state (sp)
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SN1 energy diagram
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SN2 energy diagram
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Adding s-AOs to form -MOs
Tags: bonding
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s+s Energy diagram
Tags: bonding
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23
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p+p Energy diagram
Tags: bonding
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24
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sp hybridization (energy diagram)
Tags: bonding
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25
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hybrid orbitals
Tags: bonding
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26
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hybrid orbitals
Tags: bonding
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27
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Adding p-AOs to form and -MOs
Tags: bonding
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28
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Isomers
Tags: isomers
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Butane Conformation PE
Tags: isomers
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Enantiomers
Non-superimposable mirror images.

Same physical properties except rotation of polarized light
Same chemical properties except with chiral molecules
Tags: Isomers
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31
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Diastereomers
Similar - Large in physical and chemical properties.
Tags: Isomers
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32
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Functional Group Priorities
Carboxylic Acids Carbon
Ester Es
Amide A Dignified
Nitrile Neutral
Aldehyde Atom
Ketone Kind
Alcohol And
Amine Amazing
Ether En
Double-bond Dirty
Triple-bond Threesomes
33
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Common Alkanes
34
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Common Alkane Substituents
35
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Structural (Constitutional) Isomers
Same molecular weight and molecular formula.
Different atomic connectivity.
Different physical properties.
Different chemical properties.

*Number of isomers per CH formula.
Tags: Isomers
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Stereoisomers
Same atomic connectivity, but different arrangement in space.

1. Conformational
2. Geometric
3. Enantiomers
4. Diastereomers
5. Meso compounds
Tags: Isomers
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Conformational Isomers (Conformers)
Do not need bond breaking to convert from one to another.
i.e. rotation about a bond.

Same physical and chemical properties.
Tags: Isomers
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38
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Configurational Isomers
Require bond breaking to interconvert.

1. Geometric
2. Optical
Tags: Isomers
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39
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Geometric Isomers
Stereoisomerism at a double bond or cycloalkane.
i.e. cis or trans, (Z) or (E)

Different properties when difference in net polarities
Tags: Isomers
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40
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Specific Rotation of Polarized Light
Tags: Isomers
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41
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Optical Isomers
Configurational isomerism involving single bonds.

1. Diastereomers
2. Enantiomers
3. Meso compounds
42
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Elimination reactions - important points
- more substituted bond product favored
- trans isomer favored
- anti hydrogen removed by base
43
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Oxidation
* losing hydrogens
* gaining double bond
* gaining oxygen
44
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Mechanism of catalytic hydrogenation of a double bond
45
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Lewis acids versus bases
* Lewis acid = e acceptor.
* Lewis base = e donator (benevolent).
46
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Markovnikov's Rule
the goal is to produce the most stable carbocation in alkyl halide addition to double bonds.
addition of the halogen to the more substituted carbon in the double bond.
47
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Alkyne physical properties
* higher boiling points than alkenes
* more polarized than alkenes
* internal alkynes BP > terminal alkynes BP
* terminal alkynes fairly acidic (PKA~25) due to high s character (50%), stabilize negative charge.
Tags: physical properties
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Kartensatzinfo:
Autor: jmilber
Oberthema: Chemistry
Thema: MCAT
Veröffentlicht: 24.06.2010
Tags: MCAT, chemistry
 
Schlagwörter Karten:
Alle Karten (47)
bonding (7)
Isomers (8)
isomers (2)
physical properties (3)
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