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O. Chem. Flashcards

1
Q

What are the 12 (1-12C) straight chain alkanes called

A 
Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane
Undecane
Dodecane
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2
Q

What is the formula for straight chain alkanes

A

C(n)H(2n)+2

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3
Q

What are the steps in naming organic compounds

A
  1. Find the largest carbon backbone
  2. Number the chain so the substituents are in the lower numbers
  3. Name the substituents
  4. Assign each substituent it’s carbon number
  5. List the substituents in alphabetical order (not counting the di,tri,tetra, sec, tert)(cyclo, iso and neo do count)
  6. Assign (cis, trans, R, S, Z, E)
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4
Q

if there are two equally long carbon backbones, which one do you use for IUPAC naming

A

the more substituted one

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5
Q

What is a t-butyl substituent

A
  • C(CH3)3
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6
Q

What is a neopentyl substituent

A
  • CH2C(CH3)3

A t-butyl with a CH2 first

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7
Q

What is an isopropyl substituent

A
  • C(CH3)2H
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8
Q

What is a sec-butyl substituent

A

An isopropyl with an extra carbon on one side

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9
Q

what is an iso butyl substituent

A

an isopropyl with an extra carbon in front

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10
Q

What do you do if there are more than one of a given substituent

A

use di-, tri-, tetra-

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11
Q

How do commas and dashes work in IUPAC naming

A

commas between two numbers, dashes between words and numbers

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12
Q

How do you start naming organic compounds where the largest carbon backbone is found in a ring

A

Assign C1 to be the MOST substituted carbon, and do the numbering so that the substituted carbons have the lowest numbers

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13
Q

What are olefins

A

alkenes

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14
Q

When double bonds are present how do you chose which carbon chain of equal length to use

A

the one with more double bonds (assuming it is tied for the longest chain with a double bond)

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15
Q

so what happens if you have a carbon chain of 5 with a double bond, or a carbon chain of 6 without the double bond

A

you use the 5 C chain with the double bond as your backbone

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16
Q

What does the term vinyl-mean

A

vinyl groups are monosubstituted ethylenes

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17
Q

What does the term allyl mean

A

allyl groups are monosubstituted propylenes (at the C3 location)

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18
Q

What is vinyl-chloride

A

a substituent ethylene with a chlorine at the C2 end

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19
Q

What is acetylene

A

ethyne

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20
Q

what is t-butyl bromide

A

C(CH3)3Br

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21
Q

Which has priority when numbering a chain an alcohol, a double bond, or a triple bond

A

Alcohol has priority

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22
Q

What are diols

A

molecules with 2 hydroxyl groups

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23
Q

what are vicinal molecules

A

molecules with hydroxyl groups on adjacent carbons

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24
Q

what are geminal molecules

A

molecules with 2 hydroxyl groups on the same carbon

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25
Q

What are ethers

A

ethers are 2 carbon chains that have an O inbetween them

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26
Q

what is an ether functional group called

A

alkoxy-

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27
Q

how are ethers named (IUPAC)

A
  1. find the longest carbon chain with the ether
  2. use the shorter chain as a substituent
  3. number the ether
  4. put -oxy- in before you name the carbon chain
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28
Q

how are common names of ethers derived

A

name the two alkyl groups in alphabetical order and add the word ether

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29
Q

What is an aldehyde

A

a carbonyl group with at least one H off of it

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30
Q

what is the suffix for aldehydes

A

-al

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31
Q

Where is the C1 in aldehydes

A

the carbonyl carbon

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32
Q

What is formaldehyde

A

methanal

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33
Q

What is acetaldehyde

A

ethanal

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34
Q

what is propionaldehyde

A

propanal

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35
Q

What is the suffix for ketones

A

one

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36
Q

how are ketones named

A
  1. number the chain giving the ketone the lowest number possible
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37
Q

What is acetone

A

2 propanone

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38
Q

what is the suffix for carboxylic acids

A
  • oic acid
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39
Q

where is the C1 for carboxylic acids

A

the carbonyl carbon

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40
Q

what is formic acid

A

methanoic acid

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41
Q

What is acetic acid

A

ethanoic acid

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42
Q

What is the suffix for amines

A

-amine

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43
Q

what is the substituent name for amines

A

amino

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44
Q

What do you do when a nitrogen is in the chain (like an ether)

A

you use N-(then name the shorter carbon substituent)

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45
Q

What are isomers

A

structures with the same molecular formula, but differ in structure

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46
Q

what are structural isomers

A

isomers with ONLY the same molecular formula

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47
Q

what are stereoisomers

A

isomers with the same molecular formula and connectivity

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48
Q

What are geometric isomers

A

compounds that differ in the position of substituents attached to a double bond

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49
Q

When do you use E or Z to name a double bond

A

when there are multiple substituents

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50
Q

how do you assign E and Z to double bonds

A
  1. Find the highest atomic weight atom bonded to both sides of the double bond
  2. if they are the same find the atomic weights bound to that one
  3. if the higher priority are on the Zame Zide its Z
  4. if the higher priority groups are on epposite sides its E
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51
Q

What is a chiral object

A

one that is not superimposable on its own mirror image

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52
Q

How do you assign R and S to stereocenters

A
  1. Assign priority to the 4 groups based on atomic number
  2. rotate it so #4 points away from you
  3. If 1-2-3 is clockwise = R, if it is counterclockwise = S
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53
Q

what are the horizontal lines like in a fischer projection

A

sticking out of the page

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54
Q

enantiomers have identical chemical and physical properties with one exception…

A

optical activity

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55
Q

what does it mean when a compound is optically active

A

if it has the ability to rotate plan-polarized light

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56
Q

How is the rotation of light between two enantiomers related

A

they rotate light the same distance, but in opposite directions

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57
Q

what is an compound that rotates light to the right called

A

Dextrorotary (+)

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58
Q

What is a compound that rotates light to the left called

A

levorotary (-)

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59
Q

From which perspective do you assign directions to light rotation

A

from someone seeing the light approach them

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60
Q

What determines the amount of rotation caused by a compound to light

A

the number of molecules that the light wave encounters (concentration of the optically active compound and length of the tube through which the light passes)

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61
Q

what is the equation for specific rotation

A 
specific rotation ([a]) = 
observed rotation (a)/concentration*length
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62
Q

What is a racemic mixture

A

a mixture of equal parts of both the + and - enantiomers so that no optical activity occurs

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63
Q

how many possible stereoisomers are there for a molecule with n stereocenters

A

2n

5 stereocenters = 10 possible stereoisomers

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64
Q

What are enantiomers

A

nonsuperimposable mirror images

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65
Q

what are diastereomers

A

stereoisomers that are not mirror images

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66
Q

can enantiomers and diastereomers be seperated by physical means

A

no to enantiomers

yep to diastereomers

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67
Q

What are meso compounds

A

a compound with chiral centers but has a plane of symmetry
not optically active
superimposable mirror image

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68
Q

how do you remember what meso compounds are

A

MeSo

Mirror plane of Symmetry

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69
Q

What are conformaitonal isomers

A

compounds that differ only by the rotation about one or more single bond

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70
Q

What is the most stable conformation in newman projections

A

staggered or anti large groups
180 degrees away from each other
antiperiplanar

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71
Q

What is gauche in newman projections

A

the large groups are 60 degrees apart

higher in energy than staggered conformation

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72
Q

What is eclipsed in newman projection

A

when the bond is rotated so that the front and back groups all overlap

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73
Q

what is totally eclisped in newman projections

A

when the two largest groups are overlapped

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74
Q

what is the order of energy in newman projections from lowest to highest of the different orientation

A
  1. stagered (anti)
  2. gauche
  3. eclipsed
  4. totally eclipsed
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75
Q

What are the three types of strain that influence cyclic conformations

A

angle strain
torsional strain
nonbonded strain

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76
Q

what shape do cyclobutanes take

A

a puckered shape

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77
Q

what shape do cyclopentanes take

A

envelope shape

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78
Q

what are the three types of shapes cyclohexanes take (in order of stability)

A
  1. chair
  2. boat
  3. twistboat
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79
Q

which is more stable large groups axial or equitorial

A

equitorial

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80
Q

What is a node in atomic orbitals

A

locations where the probability of finding an electron in the orbital is 0

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81
Q

how many nodes do s orbitals have

A

0

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82
Q

how many nodes do p orbitals have

A

1

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83
Q

how many nodes do d orbitals have

A

2

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84
Q

what is a molecular orbital

A

when two atomic orbitals combine

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85
Q

When does a bonding orbital occur

A

when the signs of the wave functions are the same

when they are opposite it creates a non-bonding orbital

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86
Q

what is a sigma bond

A

when two atomic orbitals overlap head to head

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87
Q

what is a pi bond

A

when two p-orbitals overlap in parallel fashion

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88
Q

What is a double bond (MO theory)

A

when both a sigma and a pi bond is formed between two atoms

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89
Q

What is a triple bond (MO theory)

A

when a sigma bond and two pi bonds are formed between two atoms

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90
Q

are pi bonds or sigma bonds stronger

A

sigma

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91
Q

are long or short sigma bonds stronger

A

short

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92
Q

what is an sp3

A

when one s orbital and 3 p orbitals are mixed to create 4 sp3 hybrid molecular orbitals

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93
Q

what is isobutane

A

C (CH3)3 H

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94
Q

What is neopentane

A

C(CH3)4

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95
Q

What is a primary, secondary, tertiary, and quaternary Carbon

A 
primary = Bonded to 1 C
secondary = bonded to 2 C
tertiary = bonded to 3 C
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96
Q

What happens to boiling point, melting point, and density as chain length increases, and as branching increases

A

the longer the chain the higher the BP,MP, and Density are

the more branching there is the lower the BP, MP, and density are

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97
Q

What is free-radical halogentation

A

the addition of a halogen by substitution

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98
Q

what are the steps of free radical halogenation

A
  1. Initiation
  2. Propagation
  3. Termination
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99
Q

How does initiation happen

A

Diatomic halogens are cleaved by heat or light creating two radicals

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100
Q

What are radicals

A

species with unpaired electrons

they are very reactive

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101
Q

How does propagation happen

A
  1. The halogen radical reacts with an alkane, removing an H, Leaving a radical alkane
  2. That radical alkane can react with a diatomic halogen creating an alkyl halide, and leaving another halogen radical
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102
Q

How does termination happen

A

two free radicals combine to form a stable molecule

can be 2 radical halides, 2 radical alkanes, or one of each

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103
Q

Where does bromine attack during free radical halogenation

A

bromine replaces a H on the most substituted C, because it is the most stable place for the radical

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104
Q

Where does chlorine attack during free radical halogenation

A

because the reaction is so fast it happens it is fairly random between carbons.

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105
Q

What are combustion reactions

A

The reaction of alkanes with O2 to form

H2O, CO2, and Heat

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106
Q

What is pyrolysis

A

the breaking down of a molecule by heat

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107
Q

what is another name for pyrolysis

A

cracking

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108
Q

What happens in pyrolysis

A

alkane C–C bonds are broken causing to alkyl radicals.

those radicals combine to form all sorts of alkanes

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109
Q

what is disproportionation

A

when an alkyl radical transfers a H to another radical producing an alkane and an alkene

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110
Q

What are nucleophiles

A

electron-rich species that are attracted to positively polarized atoms

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111
Q

what determines how good a nucleophile is if it has the same attacking group?

A

if they have the same attacking group, nucleophilicity is roughly correlated to basicity.
RO- > HO- > RCO2- > ROH > H20

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112
Q

what determines how good a nucleophile is if it doesn’t have the same attacking group

A

the bigger the atom, the better it is as a nucleophile

CN- > I- > RO- > HO- > Br- > Cl- > F- > H20

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113
Q

what determines how good a nucleophile is in aprotic solvents

A

it is directly related to bascity

F- > Cl- > Br- > I-

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114
Q

What determines the quality of leaving groups

A

weak bases make the best leaving groups

I- > Br- > Cl- > F-

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115
Q

What is the mechanism of Sn1 reaction

A
  1. dissociation of a molecule into a carbocation and a good leaving group
  2. nucleuophilic attack on the carbocation
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116
Q

Where will Sn1 reactions occur the most

A

at the most substituted carbon

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117
Q

what is the slow step in an Sn1 reaction

A

the dissociation of a molecule into the carbocation

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118
Q

what determines the rate of Sn1 reactions

A

the concentration of the original molecule (not the concentration of the nucleophile

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119
Q

what things can increase the rate of Sn1 reactions

A
  1. highly substituted carbons
  2. highly polar-protic solvents
  3. good leaving groups (weak bases)
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120
Q

What is the mechanism of an Sn2 reaction

A
  1. nucleophile attacks the carbon opposite to the leaving group, bond strength shifts from the LG to the Nu. and the leaving group leaves
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121
Q

what does the nucelophile of an Sn2 reaction need to be like

A

strong and not sterically hindered

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122
Q

what determines the rate of Sn2 reactions

A

both the substrate, and the Nu

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123
Q

What order is an Sn2 reaction

A

2nd order

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124
Q

What does Sn1 reactions do to chirality

A

becuase it goes through a planar carbobation, it will produce two racemic products

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125
Q

What does an Sn2 reaction do to chirality

A

it keeps it chiral but flips it

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126
Q

what is the equation for finding double bond equivalents (degree’s of unsaturation)

A

N = 1/2 (2n+2-m)

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127
Q

do cis or trans alkenes have higher boiling/melting point

A

trans-alkenes have a higher melting point (symmetry)

cis-alkenes have a higher boiling point (polarity)

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128
Q

what is one physical difference between internal and external alkenes

A

internal alkenes have a higher boiling point than terminal (external boiling points)

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129
Q

What is another name for an E1 reaction

A

unimolecular elimination

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130
Q

what is the mechanism for E1 reactions

A
  1. Leaving group leaves creating a carbocation

2. a base removes a proton and a double bond is formed

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131
Q

What determines the rate of E1 reactions

A

only the rate of the substrate (it goes through a carbocation intermediate)

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132
Q

What factors favor E1

A
  1. highly polar solvents
  2. highly branched carbon chains (more substituted)
  3. good leaving groups
  4. weak nucleophiles
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133
Q

How do you favor E1 over Sn1

A

with high temperatures

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134
Q

What factors favor Sn1 reactions

A
  1. highly polar protic solvents
  2. highly branched carbon chains (more substituted)
  3. good leaving groups
  4. weak nucleophiles
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135
Q

what is another name for Sn2 Reactions

A

bimolecular elimination

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136
Q

What is the mechanism for Sn2 Reactions

A
  1. a strong base removes a proton, causing the anti halide to leave, resulting in a double bond
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137
Q

What kind of double bond is favored in an Sn2 reaction

A

more substituted

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138
Q

What situations favor E2 over Sn2

A
  1. highly substituted carbon chains

2. Strong bases favor E2 (weak bases favor Sn2)

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139
Q

What are stereospecific reactions

A

reactions that favor one stereoisomer over the others

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140
Q

What are reduction reactions to a double or triple bond

A

reactions that add hydrogen atoms to get rid of one of the bond

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141
Q

what does H2 / Pd do

A

reduction by syn addition of two hydrogen atoms

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142
Q

What things attack and add to double or triple bonds

A

electrophiles

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143
Q

How do HX’s add to double bonds

A
  1. a hydrogen is added to the less substituted side and a carbocation + is on the more substituted carbon
  2. then the X- adds to the + carbon on the carbocation
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144
Q

What is markovnikov’s rule

A

that the carbocation is on the more substituted carbon, and the H+ adds to the less substituted side

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145
Q

how do X–X’s add to double bonds

A
  1. The double bond attacks the X, displacing an X-, and forming a cyclic halonium ion (three atom ring with the X at the top)
  2. the X- then attacks from below the ring, and the two X’s end up being added anti
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146
Q

What can happen when adding XX’s to a double bond, in a nucleophilic solution

A

the nucleophiles can add during the final step and have only one X added`

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147
Q

When can water be added to alkenes

A

under acidic conditions (H+/H20)

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148
Q

What happens when water is added to alkenes in acidic condition

A
  1. the double bond is protonated according to Markovnikovs rule creating a carbocation
  2. the carbocation reacts with water, and the water loses it’s proton
  3. final product is an OH added to the most substituted carbon
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149
Q

what happens in free radical addition of a double bond that is different from most reaction

A

it doesn’t follow markovnikov’s rule because the most stable radical is formed, not the most stable carbocation
(the halogen is added to a the less substituted carbon

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150
Q

What is hydroboration of a double bond (BH3/THF)

A

When BH3 is added to a double bond, then it is typically replaced with OH by (H2O2/-OH)

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151
Q

How does hydroboration of a double bond occur

A
  1. A transition state is created where BH2 begins to add to the less substituted side, while the H adds to the other (Syn)
  2. The bond between the BH2 and H breaks and a syn anti-markovnikov product is formed
  3. Oh replaces the BH2
152
Q

What does potassium permanganate KMnO4 do to double bonds

A

That depends on if is in a cold dilute solution or a hot basic solution

153
Q

What does potassium permanganate KMnO4 do to double bonds in cold dilute solutions

A

they produce syn 1,2 diols

Oh is added to syn to both sides of the double bond

154
Q

what does potassium permanganate KMnO4 do to double bonds is hot basic solutions

A

that depends on whether the alkene is terminal or not

155
Q

what does potassium permanganate KMnO4 do to non-terminal double bonds is hot basic solutions

A

two molar equivalents of carboxylic acids are formed (Basically you cut the molecule at the double bond and create two carboxylic acids out of it, with the OH group where the double bond used to be)

156
Q

what does potassium permanganate KMnO4 do to terminal double bonds is hot basic solutions

A

it will create a carboxylic acid and a CO2 molecule

157
Q

What happens to a alkene that reacts with O3, CH2Cl2/(Zn/H2O)

A

the double bond is cleaved and turned into 2 carbonyls

put two O’s in the middle of the double bond and separate it

158
Q

What happens to an alkene that reacts with O3, Ch2Cl2/NaBH4, CH3OH

A

the double bond is split, just like in the other O3 reaction, but then the carbonyls are reduced to OH groups

159
Q

what happens when alkenes are reacted with CH3CO3H and MCPBA

A

an epoxide is produced where the double bond was

160
Q

what is another name for an epoxide

161
Q

How is polymerization done to alkenes

A

with a radical

162
Q

What happens when an alkene is reacted with (radical carbon chain), heat, and pressure

A

polymerization from the monomeric alkene

163
Q

How are alkynes created

A

reacting a di-anti halogenic alkane with heat and a strong base

164
Q

What happens when a terminal alkyne is reacted with n-BuLi

A
  1. the hydrogen is removed creating an acetylide ion

2. the acetylide ion acts as a nucleophile and does nucleophilic displacement of a alkyl halide

165
Q

What happens when you react alkynes with
H2,Pd/BaSo4
———————>
quinoline (lindlars catalyst)

A

two hydrogens are added cis to each other, and a double bond is retained

166
Q

What are the two ways to reduce an alkyne and keep a double bond

A

H2,Pd/BaSo4
———————>
quinoline (lindlars catalyst)

Na,NH3 (liq)

167
Q

What happens when you react an alkyne with Na, NH3 (liq)

A

two hydrogens are added trans to each other and a double bond is retained

168
Q

what happens when you add Br2 to an alkyne

A

Br’s are added trans to each other and the double bond is retained. or if there is enough Br2, the reaction will proceed until Br2 was added to each side twice.

169
Q

what happens in free radical addition to triple bonds

A

the X (radical) and H are added to take it down to a double bond. Results in the trans isomer.

170
Q

What happens when an alkyne is reacted with BH3

A
  1. syn addition of H and BH2 occurs
  2. then the BH2 is replaced with an H by acetic acid
  3. a cis double bond is the final product
171
Q

what happens when a terminal alkyne is reacted with
R2Bh
——–>
H2O2, OH-

A

an Oh is added to the terminal end, an H is added to the other side. Double bond is retained.
then it can tautomerize into an aldehyde

172
Q

What happens to alkynes reacted with

1) KMnO4, OH-
- ———————>
2) H+

A

the triple bond becomes two carboxylic acids (the two carbons in the triple bond become the carbonyl carbons of the carboxylic acids)

173
Q

What happens to alkynes reacted with

1) O3, CCl4
- —————->
2) H2O

A

the triple bond becomes two carboxylic acids (the two carbons in the triple bond become the carbonyl carbons of the carboxylic acids)

174
Q

What is the electron rule for aromaticity

A

4n + 2 pi electrons in order for the molecule to be aromatic

175
Q

what happens to aromaticity when you have $n pi electrons

A

you have an anti-aromatic structure (less stable)

176
Q

What is toluene

A

a monosubstituted benzene with a CH3 group

177
Q

what is phenol

A

a monosubstituted benzene with an OH group

178
Q

what is analine

A

a monosubstituted benzene with an NH2 group

179
Q

what is anisole

A

a monosubstituted benzene with an OCH3 group

180
Q

What is benzoic acid

A

a monosubstituted benzene with an CO2H group

181
Q

What is naphthalene

A

2 hooked benzene rings

182
Q

what is anthracene

A

3 hooked benzene rings

183
Q

what is pyridine

A

a benzene with a N(electron pair group in place of a C)

184
Q

What is pyrrole

A

a 5 carbon ring, with two double bonds, and an NH(electron pair) group replacing one of the carbons

185
Q

What happens when benzene is reacted with Br2 or Cl2 and FeCl3, FeBr3, or AlCl3

A

the benzene is halogenated once

186
Q

what happens when benzene is reacted with F2 or I2

A

F2 usually leads to multisubstituted benzenes,

I2 usually doesn’t react

187
Q

What happens when benzene is reacted with
SO3/H2SO4
——————–>
heat

A

suflonic acid is formed

SO3H is monosubstituted to benzene

188
Q

What happens when benzene is reacted with
H2SO4
————>
HNO3

A

NO2 is monosubstituted to benzene

189
Q

what happens when benzene is reacted with a carbocation electrophile (carbonyl with a halogen) and a lewis acid (AlCl3)

A

Freidel-Crafts acylation

the carbocaiton electrophile is added to benzene

190
Q

What kind of directors are electron donating groups

A

activating, Ortho/para directors

191
Q

What are some activators

A

NH2, NR2, OH, NHCOR, OR, OCOR, R

192
Q

What kind of directors are weakly electron withdrawing groups

A

deactivating, Otrho/para directors

193
Q

what are some examples of weakly withdrawing groups

A

F, Cl, Br, I

194
Q

What kind of directors are strongly electron withdrawing groups

A

deactivating, meta directors

195
Q

what are some examples of strongly electron withdrawing groups

A

NO2, SO3H, Carbonyl compounds (COOH, COOR, COR, COH)

196
Q

What happens when benzene is reacted with
H2, RH/C
————–>
100 C

A

The benzene is reduced to cyclohexane

(can also be done with H2, Pd

197
Q

what is m-cresol

A

an phenol with a methyl group added meta

198
Q

what happens to boiling points of alcohol

A

they are higher than similar Hydrocarbons because they can H bond, this also makes them water soluble

199
Q

What are the three reaction mechanisms for alcohol and ether reactions

A
  1. Sn1/Sn2 nucleophilic substitution
  2. Elecrophilic addition to a double bond
  3. nucleophilic addition to a carbonyl
200
Q

What is the oxidation/reduction continuum for primary alcohols

A

Primary alcohols aldehydes carboxylic acids

reduction oxidation

201
Q

What is the oxidation/reduction continuum for secondary alcohols

A

secondary alcohols ketones

reduction oxidation

202
Q

What happens in Sn1/Sn2 nulceophilic substitutions to alkyl halides

A

they can be turned into alcohols

203
Q

What happens when an alkene is reacted with H2O

A

cis addition of H and OH

204
Q

what happens to an carbonyl that is reacted with CH3MgBr

A

it is reduced to an alcohol

205
Q

what happens when carbonyl groups are reacted with

1) LiAlH4
- ————->
2) H3O+

A

They are reduced to form alcohols

206
Q

What happens when carbonyl groups are reacted with

1) NaBH4
- ————–>
2) H3O+

A

The carbonyl group is reduced to form an alcohol

207
Q

what is the difference in reduction between LiAlH4 and NaBH$

A

LiAlH4 is more powerful and can reduce carboxylic acids and esters, while NaBH4 can’t

208
Q

what happens when you add a para bromo analine to
HNO2
———>
H2SO4

A

It turns into para bromo phenol

209
Q

What happens when an alcohol is added to strongly acidic solutions (H2SO4)

A

it is dehydrated to alkenes

210
Q

When alcohols are dehydrated in strong acid, what are the major and minor products

A

major = more substituted double bond
minor = less substituted double bond
(this is because the more subsituted went through a more stable carbocation)

211
Q

is OH a good or bad leaving group

212
Q

what can be done to make OH a good leaving group

A

protonate it
convert it to tosylate
form an inorganic ester

213
Q

What happens when you react an alcohol with HBr

A

the OH is protonated by HBr, then the Br- replaces the good OH2 + leaving group

214
Q

What happens when you react an alcohol with tosyl chloride then NaI

A

the tosyl chloride reacts with the OH group making it a good leaving group, this is then replaced by I

215
Q

What happens when you react an alcohol with SOCl2

A

The hydroxyl of the alcohol gets replaced by the Cl group

216
Q

What happens when you react an alcohol with PBr3

A

The hydroxyl group of the alcohol gets replaced by Br

217
Q

What happens when you react an alcohol with PCC

A

it converts primary alcohols to aldehydes
it converts secondary alcohols to ketones
it doesn’t work on tertiary alcohols

218
Q

What happens when you react an alcohol with
Na2Cr2O7
—————->
H2SO4

A

it is oxidizes primary alcohols to carboxylic acids

it oxidizes secondary alcohols to ketones

219
Q

what happenswhen you react an alcohol with
CrO3, H2SO4
———————->
acetone

A

primary alcohols are converted to carboxylic acids

secondary alcohols are converted to ketones

220
Q

What is an ether

221
Q

how are ether’s named

A

small chain as the prefix, large chain as the suffix

____oxy_____

222
Q

What is oxyethane

A

an 4 carbon ring with an O instead of a C

223
Q

what is THF

A

a 5 carbon ring with an O instead of a C

224
Q

how are ethers synthesized

A

reacting a metal alkoxide with a primary alkyl halide (becasuse for Sn2 to happen the alkyl halide cannot be sterically hindered)

225
Q

what happens when you react RC-O- Na+ with R(1)-X

A

RC-O-R1 is formed via Sn2 (O- attacks R(1))

226
Q

what happens when you react phenol and a primary alkyl halide with NaOH, H2O

A

you get a ether (phenol + alkane)

227
Q

what happens when you react a alcohol with base and H+

A

you get internal Sn2, which forms an epoxide

228
Q

what happens when you react a double bond with MCPBA

A

you get an epoxide formed

229
Q

What is an ether

230
Q

how are ether’s named

A

small chain as the prefix, large chain as the suffix

____oxy_____

231
Q

What is oxyethane

A

an 4 carbon ring with an O instead of a C

232
Q

what is THF

A

a 5 carbon ring with an O instead of a C

233
Q

how are ethers synthesized

A

reacting a metal alkoxide with a primary alkyl halide (becasuse for Sn2 to happen the alkyl halide cannot be sterically hindered)

234
Q

what happens when you react RC-O- Na+ with R(1)-X

A

RC-O-R1 is formed via Sn2 (O- attacks R(1))

235
Q

what is the prefix used when a ketone is a functional group

236
Q

what happens when you react a alcohol with base and H+

A

you get internal Sn2, which forms an epoxide

237
Q

what happens when you react a double bond with MCPBA

A

you get an epoxide formed

238
Q

What are peroxides, and how are they formed

A

they are ROOR’s and they are formed by ethers reacting with O2 in the air

239
Q

How is cleavage of ethers performed

A

in high temperatures, in the presence of HBr, or HI

240
Q

which carbon is attacked in the opening of an epoxide

A

the more substituted C in the presence of acid

the least substituted C in the presence of base

241
Q

What is the product of axid-catalysed epoxide openin

A

OH and halide on opposite carbons

242
Q

what is the product of base-catalysied epoxide opening

A

OH and halide on the same carbon

243
Q

what is the prefix used when aldehyde is a functional group

244
Q

what is the prefix used when a ketone is a functional group

245
Q

what is more polar, alcohols or ketones and aldehydes

A

alcohols, since they can H-bond

246
Q

What are the three ways to make aldehydes and ketones

A
  1. oxidation of alcohols
  2. Ozonolysis of alkenes
  3. Friedel-crafts acylation
247
Q

What is an enol

A

when a ketone loses an alpha proton, the proton attaches to the O, and the double bond switches place

248
Q

what are tautomers

A

two isomers that differ only in the placement of a proton

249
Q

What happens when Nitrogen containing compounds react with aldehydes and ketones

A

the NH2R becomes =NR and water is lost

250
Q

What is the most common form of addition to carbonyl’s

A

nucleophilic addition to the carbonyl carbon. (if there are no good leaving groups the O gets protonated and thats it)

251
Q

What is hydration of a carbonyl

A

when H2O acts as an Nu and attacks the carbonyl carbon. final product is a diol.

252
Q

What is an acetal/hemiacetal

A

a hemi acetal is when an alcohol Nu adds to a ALDEHYDE, making an ether.
an acetal is when it does so twice

253
Q

what is a ketal/hemiketal

A

a hemi ketal is when an alcohol Nu adds to a Ketone, making an ether.
an ketal is when it does so twice

254
Q

What happens when a ketone is reacted with ROH

A

once it makes a hemiketal, twice it makes a ketal

255
Q

What happens when an ylide is reacted with a ketone/aldehyde

A
  1. it Nu attacks the carbonyl Carbon
  2. it forms a cylcobutane with P and O
  3. double bonds are created (O=P, C=C)
256
Q

What happens when you add NH3 to a ketone/aldehyde

A

the NH2 nu adds to the reaction, then H2O is lost, and an imine forms

257
Q

what is an imine

A

when N is double bound to a C

258
Q

What happens when Nitrogen containing compounds react with aldehydes and ketones

A

the NH2R becomes =NR and water is lost

259
Q

what happens when an aldehyde/ketone is reacted with
Hg(Zn)
———–>
HCl

A

the carbonyl is removed

260
Q

How is aldol condensation done

A
  1. in a base the aldehyde is converted to it’ enol form
    2 the enol form Nu attacks another aldehyde and adds to it.
  2. the O- gets protonated to form an aldol
261
Q

what does the alpha carbon substituent do to the acidity of carboxylic acids

A 
withdrawing groups ( Cl, NO2) increase acidity
donating groups ( NH2, OCH3) decrease acidity
262
Q

What does the wittig reaction do

A

converts aldehydes and ketones into alkenes

263
Q

what happens to the witting reagent

A 
it starts out as (C6H5)3P
added to CH3Br
= (C6H5)3P+CH3
added to base
= (C6H5)3P=CH2
Resonance
(C6H5)3P+---CH2- (ylide)
264
Q

What happens when an ylide is reacted with a ketone/aldehyde

A
  1. it Nu attacks the carbonyl Carbon
  2. it forms a cylcobutane with P and O
  3. double bonds are created (O=P, C=C)
265
Q

What happens when you have an aldehyde reacted with KMnO4, CrO3, Ag2O

A

it is converted into a carboxylic acid

266
Q

What happens when you react an aldehyde or ketone with LAH or NaBH4

A

it is reduced to an alcohol

267
Q

What happens when you react an aldehyde or ketone with H2NNH2 ( wolff-kishner)

A

the NNH2 replaces the O,

in basic heated solutions the N2 will leave, and nothing will remain

268
Q

what happens when an aldehyde/ketone is reacted with
Hg(Zn)
———–>
HCl

A

the carbonyl is removed

269
Q

What can soaps do

A

solubilize nonpolar organic compounds in aqueous solutions becuase they have both a polar and a nonpolar end

270
Q

What happens in Nu substitution in carboxylic acids

A

the Nu attacks and the negative O is formed just like normal. But then the OH is protonated and leaves when the C=O bond reforms
(simply the Nu replaces the OH)

271
Q

what happens to the acidity of the H’s in dicarboxylic acids

A
  1. one carboxylic acid makes the other more acidic (electron withdrawing)
  2. When that one loses it’s proton, the - charge causes the 2nd carboxylic acid to be less acidic
272
Q

where are beta dicarboxylic acids highly acidic

A

the alpha H’s

273
Q

what happens when you react aldehydes with KMnO4

A

you get a carboxylic acid

274
Q

What happens when you react primary alcohols with KMnO4

A

you get a carboxylic acid

275
Q

What is decarboxylation of a carboxylic acid

A

when a carboxylic acid loses CO2

276
Q

what happens when you react an alkyl halide with

HCN, then in basic or acidic solutions

A
  1. the CN will replace the halogen

2. the RCN will then dissociate into a carboxylic acid and ammonia

277
Q

How is soap formation done

A

reacting a long chain carboxylic acid with KOH or NaOH

278
Q

What can soaps do

A

solubilize nonpolar organic compounds in aqueous solutions becuase they have both a polar and a nonpolar end

279
Q

What happens in Nu substitution in carboxylic acids

A

the Nu attacks and the negative O is formed just like normal. But then the OH is protonated and leaves when the C=O bond reforms

280
Q

what happens when carboxylic acids are reacted with LAH

A

they are reduced to aldehydes, then they can be reduced to alcohols

281
Q

How are esters formed

A

when they react with alcohols in acidic conditions

282
Q

What happens when carboxylic acids are reacted with primary alcohols in acidic conditions

A

the alcohol Nu attacks and replaces the OH group, forming an ester

283
Q

What happens when you react SOCl2 with a carboxylic acid

A

you get an acid chloride

284
Q

What is decarboxylation of a carboxylic acid

A

when a carboxylic acid

285
Q

what happens when an acyl chloride is reacted with H2/Pd/ BaSO4 or quinoline

A

it is reduced to an alcohol or an aldehyde

286
Q

what is the order of reactivity between acyl halides, esters, amides, and anhydrides

A
  1. Acyl Halides
  2. Anhydrides
  3. Esters
  4. Amides
287
Q

what are the acyl halides

A

carboxylic acid derivatives where the Oh has been replaced by a halide

288
Q

how are acyl halides names

A

-yl halide

289
Q

what happens when carboxylic acids are reacted with SOCl2, PCl3, PCI5, or PBr3

A

an acyl halide is produced

290
Q

What happens when an acyl chloride is reacted with water

A

it undergoes hydrolysis, recreateing the carboxylic acid

291
Q

what happens when an acyl chloride is reacted with an alcohol

A

an ester is created

292
Q

what happens when anhydrides are reacted with benzene and AlCl3

A

you get a benzoketone and an carboxylate anion

293
Q

what happens when an acyl chloride is reacted with a benzene and AICI3

A

the benzene replaces the halide

294
Q

What is an anhydride

A

R-C=O__O__O=C-R

295
Q

what happens when an acyl chloride is reacted with a carboxylate salt

A

the salt attacks the acyl chloride, the chloride leaves, the C=O bond is restored, and an anhydride is created

296
Q

what can happen when a dicarboxylic acid is heated

A

it can react to form a cyclic anhydride

297
Q

what happens when anhydrides are reacted with water

A

2 carboxylic acids are formed

298
Q

what happens when you react an amide with

BrO- and then H2O

A

1) the Br adds to the N of the amide
2) the N loses it’s H and forms water (nitrene)
3) the Br leaves, the N attaches to the R opposite (isocyanate)
4) the isocyante is hydrolized by H2O to make a primary amine and CO2

299
Q

What happens when anhydrides are reacted with alcohols

A

an ester and a carboxylic acid are produced

300
Q

what happens when anhydrides are reacted with benzene and AlCl3

A

you get a benzoketone and an carboxylate anion

301
Q

What are amides

A

R-C=O__N-R__H (amino acid like)

302
Q

How are amides named

A
  1. -amide instead of -oic acid

2. anything attached to the N will be identified with the letter N

303
Q

how are amides formed

A
  1. reaction of acid chlorides with amines
  2. Reaction of acid anhydrides with ammonia
    (only primary and secondary amines work)
304
Q

how is hydrolysis of amides done

A

in acidic conditions reacting with water

305
Q

what is the hoffman rearrangement

A

amides are converted into primary amines

306
Q

what happens when you react an amide with

BrO- and then H2O

A

1) the Br adds to the N of the amide
2) the N loses it’s H and forms water (nitrene)
3) the Br leaves, the N attaches to the R opposite (isocyanate)
4) the isocyante is hydrolized by H2O

307
Q

what happens when an ester is reacted with CH3CH2MgBr (grignard)

A

one equivalent with bulky groups = a ketone

more than one equivalent = tertiary alcohol

308
Q

what is the suffix for esters

309
Q

how are esters synthesized

A

with alcohols and carboxylic acids (acid chlorides and anhydrides) under acidic conditions

310
Q

what does hydrolysis of esters give you

A

an carboxylic acid and an alcohol

311
Q

What is saponification

A

when fats (esters) as hydrolyzed under basic conditions to produce soaps.

312
Q

What happens to soaps in acidic conditions

A

they are brought back to triacylglycerols

313
Q

what are nitriles

A

C triple bonded to N

314
Q

what is transesterificitaion

A

when an alcohol attacks an ester and just makes a new ester

315
Q

What happens in claisen condensation

A

two ethyl acetates react in basic conditions to form

3-oxobutanoate

316
Q

how is reduction of an ester done, and what does it produce

A

with LAH, and it produces two primary alcohols

317
Q

what things have higher priority than amines in a carbon chain

A

OH and CO2H

318
Q

what is the prefix/suffix for amine groups

A

-amine

amino-

319
Q

What are carbamates

A

they are esters with the other side of the carbonyl being an N group

320
Q

how are nitro compounds reduced to primary amines

A

Zn

  • —–>
    dil. HCl
321
Q

what is the boiling point of amines like

A

between alkanes and alcohols

322
Q

why do tertiary amines have lower bp’s than primary or seconday amines

A

they can’t H bond

323
Q

What is nitrogen inversion

A

when nitrogen flips inside out and back quickly

324
Q

What happens when you react alkyl halides with NH3

A

the NH group replaces the Halide, then if you add it to base it becomes an alkylamine

325
Q

What does gabriel synthesis do

A

converts a primary alkyl halide into a primary amine without creating side products

326
Q

What is used in gabriel synthesis

A

o-phthalic acid (converted to phthalamide by NH3) Which is a good Nu

327
Q

how are nitro compounds reduced to primary amines

A

with
Zn
——>
dil.HCl

328
Q

What happens when you react RNO2 with
Zn
——>
dil.HCl

A

the NO2 becomes NH2

329
Q

what is the product of the hoffman elimination (exhaustive methylation)

A

you get the least substituted double bond (not like normal)

330
Q

how can you get a primary amine from a nitrile

A

LAH or H+ and a catalyst

331
Q

how can you get a amine from an aldehyde or a ketone

A
  1. react aldehyde or ketone with NH3 (NR2H, NH2R) to produce an imine
  2. react the imine with H2-Ni (raney nickel) to produce an amine
332
Q

What happens when you react an aldehyde or ketone with an amine, then H2-Ni (raney nickel)

A

you get an amine

333
Q

how do you get an amine from amides

334
Q

what happens when you react an amide with LAH

A

you get an amine

335
Q

What is the hoffman elimination (exhaustive methylation)

A
  1. you react an amine with Excess MeI (this methylates the NH2 to N(CH3)3
  2. react this with Ag2O and H2O, then heat, and the N(CH3)3 group leaves and creates a double bond
336
Q

what is the product of the hoffman elimination (exhaustive methylation)

A

you get the least substituted double bond

337
Q

When is simple distialltion used

A

to separate liquids that boil under 150 degrees and at least 25 degrees apart

338
Q

When is vacuum distillation used

A

to separate liquids that boil over 150 degrees and at least 25 degrees apart

339
Q

When is fractional distillation used

A

to separate liquids that boil with less that 25 degrees of separation

340
Q

what is unique about fractional distillations

A

it has a fractional column with inert objects of large surface area. the liquids condense and re-evaporate all the way up the column, this causes the lower boiling point one to make it to the top much quicker than the other

341
Q

What is agarose gel electrophoresis

A

its when you use gel electrophoresis to separate DNA and RNA based on size. (because it is negative you don’t need SDS)

342
Q

What are epimers

A

carbs that differ in configuration at only one carbon

343
Q

What is isoelectric focusin

A

a way to separate things based on charge

344
Q

what are the four bond vibrations that occur

A

symmetric bending
asymmetric bending
symmetric stretching
asymmetric stretching

345
Q

what causes absorption of energy in IR to be recorded

A

a change in the net dipole

346
Q

what type of vibration doesn’t show in IR

A

symmtetric stretches

347
Q

Do O2, Br2 show up on Ir

A

nope (no dipole)

348
Q

How do you know the difference between L and R carbs

A

if the last OH is on the left, then it is an L, if it is on the right, then it is a D

349
Q

how do you draw cyclic versions of fisher projected carbs

A

things on the right will be pointing down, those on the left will point up

350
Q

What are anomers

A

things that differ at the anomeric carbon

351
Q

what are alpha anomers and beta anomers

A

alpha anomers point down (axial)

beta anomers point up

352
Q

which is more favored, alpha or beta anomers

A

beta (equitorial)

353
Q

what happens when you react glucose with acid anhydride (CH3CO)2O and a base

A

all of the OH’s become CH3CO2 groups

esters

354
Q

what is a reducing sugar

A

a monosaccharide with an OH on C1

355
Q

What is oxidation of glucose do

A

converts C1 from CHO to COOH

aldehyde to carboxylic acid

356
Q

What happens when you react glucose with
Cu(OH)2
————–>
benedict solution (tollens)

A

glucose C1 is oxidized from CHO to COOH

357
Q

what happens when you react a hemiacetal (glucose) with an alcohol

A

you get an acetal (OR instead of OH) and a glycositic linkage

358
Q

What is the linkage of cellulose

359
Q

what is the linkage of starch and glycogen

A

1,4 alpha (some 1,6 alpha)

360
Q

What is the naturally occurring amino acid

A

L amino acids

361
Q

What are the negative/acidic amino acids

A

aspartic acid

glutamic acid

362
Q

What does it mean that aminoacids are amphoteric

A

they can be acids or bases

363
Q

What is the henderson hasselbach equaiton

A

pH = pKa + log [conjugate base]/[conjugate acid]

364
Q

When are amino acid bufferers best

A

within one pH unit of it’s pKa or pKb

365
Q

What are the nonpolar amino acids

A 
alanine
valine
leucine
isoleucine
proline
phenylalanine
glycine
tryptophan
366
Q

What are the polar (uncharged amino acids)

A 
Methionine
Serine
Threonine
Cysteine
tyrosine
asparagine
glutamine
367
Q

What are the basic amino acids (+)

A

arginine
lysine
histidine

368
Q

how are peptides formed

A

condensation reactions

369
Q

how are peptides cleaved

A

hydrolysis reactions

370
Q

where does trypsin cleave proteins

A

the carboxyl end of arginine and lysine

371
Q

where does chymotrypsin cleave proteins

A

carboxyl end of phenylanlanine, tyrosine, and tryptophan

372
Q

how are peptides drawn

A

from the N-terminal to the C-terminal

373
Q

what is keratin made of

A

many alpha helices

374
Q

how many AA’s away are the bonds between AA’s in alpha helices

375
Q

What are silk fibers made up of

A

beta sheets

376
Q

what is the difference between cysteine and cystine

A

cystine is two bonded cysteines

377
Q

why doesn’t proline fit into alpha helices

A

causes a kink

DAT (14 decks)

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