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Final exam prep Flashcards

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1
Q

What are covalent bonds?

A

A way that elements can share electrons with others rather than transferring them

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2
Q

Octet rule

A

Elements want eight valence electrons

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3
Q

Lewis dot structure

A

Simplified structural representations of molecules that show bonding and non-bonding electrons

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4
Q

Using this information, draw the common bonding arrangements for the atoms typically seen in organic chemistry: H, O, C (lewis)

A

Draw out

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5
Q

What is organic chemisrtry

A

The study of carbon compounds

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6
Q

Nature of carbon

A

Tetravalalent - always 4 bonds. Organic molecules have covalent bonds

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7
Q

Atoms gain lose or share valence electrons to achieve noble gas configuration. true or false

A

T

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8
Q

Can carbon form multiple covalent bonds?

A

Yes

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9
Q

Draw a tetrahedral molecule

A

Draw

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10
Q

Draw a trigonal planar molecule

A

Draw

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11
Q

Draw a linear molecule

A

Draw

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12
Q

Are all covalent bonds equivalent to each other?

A

No, due to electronegativity

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13
Q

General statement for organic compounds. Prompts, are they .. soluble in water? conduct electricity? interactions with water? water soluble?

A

Most are insoluble.
Almost all that are soluble do not conduct electricity (not electrolytes)
Only small polar organic molecules or large molecules with polar groups interact with water molecules and thus dissolve in water. Lack of water solubility for organic compounds has important consequences

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14
Q

What is a functional group?

A

An atom or group of atoms within a molecule that has a characteristic physical and chemical behaviour

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15
Q

How can organic compounds be classified?

A

In their functional groups

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16
Q

True or false: a given functional group tends to undergo the same types of reactions in every molecule that it contains?

A

True

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17
Q

Name all the functional groups (and label them if want to)

A

Alkane, Alkene, Alkyne, Aromatic, Alkyl Halide, Alcohol, Ether, Amine, Aldehyde, Ketone, Carboxylic acid, anhydride, ester, amide, thiol, disulfide, sulfide

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18
Q

What are the functional groups that are also hydrocarbons?

A

Alkanes, alkenes, alkynes, simple aromatic compounds

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19
Q

Describe an alkane

A

Alkanes have single bonds and contain no functional group. Example octane, cyclohexane

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20
Q

Describe an alkene

A

Alkenes have a carbon-carbon double-bond functional group. Example retinol, butene

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21
Q

Describe an alkyne

A

Alkyne has a carbon-carbon triple bond.

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22
Q

Describe a simple aromatic compound

A

Simple aromatic compounds contain a six-member ring of carbon atoms wit three alternating double bonds.

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23
Q

Describe an alkyl halide

A

Have a carbon-halogen bond

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24
Q

Describe an alcohol

A

Carbon is bonded to an -OH group

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25
Q

Describe an ether

A

Have two carbons bonded to the same oxygen

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26
Q

Describe an amine

A

Have a carbon bonded to an -NH2 group (draw)

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27
Q

How are amines and amides different?

A

Amines have a carbon bonded to an -NH2 amino group at the end of a molecule. Amides have a double bond between c = o and can have the amine group not on the end.

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28
Q

Draw an aldehyde

A

Draw

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29
Q

Draw a ketone

A

Draw

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30
Q

Draw a carboxylic acid

A

Draw

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31
Q

Draw an ester

A

Draw

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32
Q

Draw an amide

A

Draw

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33
Q

Draw a anhydride

A

Draw

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34
Q

Three functional groups contain sulfur. Name them..

A

Thioalcohols (thiols), sulfides and disulfides

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35
Q

Draw and identify which functional group this has: C2H7N

A

Amine

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36
Q

Draw and identify which functional group this has: C3H4

A

Alkyne

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37
Q

Draw and identify which functional group this has: C4H10O

A

Ether

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38
Q

What forms the “backbone” of a compound

A

The carbon atoms bonded together with the hydrogens on the periphery

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39
Q

What is the general formula for acylic alkanes?

A

CnH2n+2

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40
Q

Describe an isomer

A

Compounds that have the same molecular formula but different structural formulas

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41
Q

Draw the 2 isomers for C4H10

A

Draw

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42
Q

What is a straight-chain alkane?

A

Alkane that has all its carbons connected in a row

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43
Q

What is a branched chain alkane?

A

An alkane that has a branching connection of carbons

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44
Q

What is a constitutional isomer?

A

Compounds with the same molecular formula but with different connections among their atoms. Also known as structural isomers.

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45
Q

How are constitutional isomers different from their ‘non-isomer form’

A

They are chemically distinct from their ‘simple format - the non-isomer version’ and often have different structures and different

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46
Q

What is a functional group isomer?

A

When the molecular formula contains atoms other than carbon and hydrogen the constitutional isomers obtained can also be functional group isomers

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47
Q

Draw C3H8O as a single line, a structural isomer, and also as a functional group isomer

A

3 drawings, label

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48
Q

Draw all the isomers that have the formula C6H14

A

Draw 5 isomers!

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49
Q

Condensed structure, what is it?

A

A shorthand way of drawing structures which C-C and C-H bonds are understood rather than shown

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50
Q

Draw the full and condensed formula for butane

A

Draw

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51
Q

Draw the full and condensed formula for 2-methylpropane

A

Draw 2

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52
Q

Draw the line structure for C4H10

A

Draw

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53
Q

True or false: most carbon atoms in an alkane have its four bonds pointing toward the four corners of a tetrahedron

A

False, it is all carbons.

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54
Q

Various conformations of a molecule are called what?

A

Conformers

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55
Q

Describe a conformer

A

The two parts of a molecule joined by a carbon-carbon single bond in a noncyclic structure are free to spin around the bond, giving rise to an infinite number of possible conformations

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56
Q

Do molecules prefer to be the least crowded lowest energy extended conformation or not?

A

Yes, they do prefer this. They don’t want to be spatially close

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57
Q

Look at conformers and draw some out.

A

Draw

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58
Q

Who invented the system of naming in organic chemistry?

A

IUPAC (international union of pure and applied chemistry).

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59
Q

How are carbon atoms classified?

A

Based on how many other carbon atoms are attached. Degree of substitution

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60
Q

How many “Parts” does a molecule have

A

The parent and substituent groups

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61
Q

Name the prefix for carbons 1-10

A

Meth, Eth, Prop, But, Pent, Hex, Hept, Oct, Non, Dec

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62
Q

Name the suffix for all functional groups

A

Alkyl: -yl
Alkane - ane
Alkene - ene
C. acid - oic acid
Amine - amine
Alkyne - yne
Aromatic - based on ring
Alcohol - ol
Ether - ether
Ester - oate
Anhydride - anhydride
Amide - amide
Thiol - thiol
Aldehyde - al
Ketone - one

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63
Q

Draw the 4 possibilities for 4 carbon structure

A

Butyl, sec-butyl, isobutyl, text-butyl

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64
Q

Steps to naming branched chain alkanes

A
  1. Name the main chain
  2. Number C atoms, starting at the first branch point
  3. List branching substituents with name and location number (alphabetically if needed)
  4. Make a single word
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65
Q

Properties of alkanes

A

Only non-polar C-C bonds and C-H bonds. Only forces are weak intermolecular and these are influenced by weak London dispersion forces

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66
Q

Trend with alkanes boiling point and melting point

A

Increases with molecular size. The first four alkanes are gases at room temp, alkanes 5-15 are liquids and alkanes with 16+ are low melting waxy solids.

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67
Q

Why is there a trend with alkanes and boiling point?

A

London dispersion forces

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68
Q

What is it called when alkanes react with oxygen?

A

Combustion

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69
Q

What is it called when alkanes react with halogens

A

Halogenation

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70
Q

Describe combustion

A

An oxidation reaction that commonly takes place in a controlled manner in an engine or furnace

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71
Q

What are the products of complete combustion?

A

Carbon dioxide and water (and a large amount of heat is released)

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72
Q

Describe halogenation

A

Is the replacement of an alkane hydrogen by a chlorine or bromine initiated by heat or light

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73
Q

What is free radical halogenation associated with?

A

Halogenation

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74
Q

What is released during complete combustion

A

Heat - large amount

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75
Q

How many H’s are released at a time in halogenation? Why?

A

1, as if it was able to do more then they would all be replaced with halogens

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76
Q

What does complete chlorination of methane yield?

A

Carbon Tetrachloride

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77
Q

What is the placement of what goes above and below the arrow in chemistry?

A

Reactants and reagents above, solvents and catalysts below
Eg. Br2 above, light and heat below.

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78
Q

Draw 2-methyl butane with bromine

A

2-bromo-2-methylbutane

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79
Q

What is a cycloalkane?

A

An alkane that contains a ring of carbon atoms

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80
Q

For a cycloalkane, to form a closed ring it requires what?

A

An additional C-C bond and the loss of 2H atoms. Eg. C6H14 and cyclohexane (now C6H12)

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81
Q

General formula for cycloalkane

A

CnH2n

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82
Q

What are the bond angles in cyclopropane?

A

60°

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83
Q

What are the bond angles in cyclobutene?

A

90°

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84
Q

Are 5 and 6-carbon rings more or less stable than a ring with fewer carbons?

A

More stable

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85
Q

Are cyclopentane and cyclohexane stable?

A

Yes

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86
Q

Describe the properties of cycloalkanes

A

Cyclic and acylic alkanes are similar in many properties. Cyclopropane and cyclobutane are gases at room temp, whereas larger cycloalkanes are liquids or solids. They are non-polar, insoluble in water, and flammable.

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87
Q

Naming cycloalkane steps

A
  1. Use the cycloalkane name as the parent
  2. Identify and number substituents
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88
Q

Draw a line structure for 1,3-dimethylcyclohexane

A

Draw (2 options)

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89
Q

Draw a line structure for 1-(sec-butyl)-4-isopropylcyclohexane

A

Sec = secondary (to note)

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90
Q

Are alkanes saturated?

A

Yes they have as many hydrogens as possible

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91
Q

Are alkenes and alkynes saturated or unsaturated?

A

Unsaturated. They contain carbon-carbon multiple bonds

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92
Q

Naming cycloalkenes

A
  1. Locations 1 and 2 are assigned to the carbon atoms of the c=c bond. chose the way that has the lowest location values to any substituent.
  2. Write the full name
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93
Q

Common name for ethene

A

Ethylene

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94
Q

Common name for propene

A

Propylene

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95
Q

Common name for 2-methyl-1,3-butandiene

A

Isoprene

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96
Q

Common name for ethyne

A

Acetylene

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97
Q

Draw the strucutre for 3-ethyl-4-methyl-2-pentene

A

Draw

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98
Q

What causes alkenes and alkynes to differ in shape

A

The presence of multiple bonds

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99
Q

Is there rotation around a C=C double bond?

A

No - bond is rigid.

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100
Q

What is a cis isomer?

A

When two groups are on the same side of a double bond. eg. cis-2-butene

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101
Q

What is a trans isomer?

A

When two groups are on opposite sides of a double bond. Eg. trans-2-butene

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102
Q

Draw the structure for both the cis and trans isomers of 2-hexene

A

Draw

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103
Q

Properties of alkenes and alkynes

A

Non-polar, hydrophobic, alkenes and alkynes with 1-4 carbon atoms are gases at room temp, and bp increases with the size of molecules. chemically reactive at the multiple bonds.

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104
Q

What are the four main types of organic reactions?

A

Addition
Elimination
Substitutions
Rearrangements

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105
Q

What is an addition reaction?

A

Involves taking two molecules and combining them together.

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106
Q

What type of organic reaction is hydrogenation?

A

Addition (addition of an alkene with hydrogen to make an alkane)

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107
Q

What is an elimination reaction?

A

The opposite of the addition reaction. Involves one molecule losing atoms (or groups of atoms). Results in the formation of additional bonds as it becomes unsaturated.

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108
Q

The elimination of water from an alcolhol forms what?

A

An alkene (ethylene)

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109
Q

What is a substitution reaction?

A

One atom (or group of atoms) is replaced by another atom (or group of atoms) on a substrate molecule.

Eg. AB + C –> AC + B

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110
Q

What type of reaction is the halogenation of an alkane?

A

Substitution

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111
Q

Describe a rearrangement reaction

A

Involves the bonds and atoms on a molecule reorganizing. Atoms moving from one location to another. Bonds shifting from one location to another.

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112
Q

Is cis-trans isomerism an example of a rearrangement reaction

A

Yes

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113
Q

What type of reaction is an alkene to an alkyne typically?

A

Addition

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114
Q

A reagent can be added to the multiple bond to yield a saturated product. What type of bonds will the product now have?

A

Single bonds only

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115
Q

What do these involve the addition of? Hydrogenation, halogenation, hydrohalogenation, hydration?

A

Hydrogenation: H2
Halogenation: Cl2 or Br2
Hydrohalogenation: H-Cl or H-Br
Hydration: H-OH

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116
Q

What is the addition of H2 to alkenes and alkynes called?

A

Hydrogenation. Also needs a metal catalyst to yield an alkane

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117
Q

How can hydrogenation be shown in a lab?

A

Using a balloon and an adaptor

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118
Q

Addition reaction of alkene example

A

An industrial hydrogenation reactor is designed to operate at higher pressure

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119
Q

Describe hydrogenation

A

This process is used commercially to convert unsaturated vegetable oils to saturated fats used in margarine and cooking fats. This creates trans fatty acids (which are bad!).

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120
Q

The addition of Cl2 and Br2 to alkenes and alkynes is halogenation. Specifically for alkenes and alkynes what does this produce?

A

1,2-dihaloalkane addition products

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121
Q

What is a common halogen that can be used as a test for multiple bonds and unsaturation of fats?

A

Bromine

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122
Q

What is the addition of HBr and HCl to alkenes?

A

Hydrohalogenation

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123
Q

What do alkenes react with to yield alkyl bromides

A

Hydrogen bromide

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124
Q

What do alkenes react with to yield alkyl chlorides?

A

Hydrogen chloride

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125
Q

Draw the addition of HBr to 2-methylpropene

A

Draw

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126
Q

What is Markovnikov’s rule and what does it help us to predict?

A

This rule helps us to predict the major product arising from addition reactions such as hydrohalogenation. It predicts where the X goes.

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127
Q

Markovnikov’s rule says that the hydrogen atom attaches where?

A

To the carbon with more H-atoms

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128
Q

Markovnikov’s rule says that the X attaches where?

A

To the carbon with fewer H-atoms

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129
Q

What happens if an alkene has equal numbers of H atoms attached to the double-bond carbons?

A

Both possible products are formed in approximately equal amounts.

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130
Q

The addition of water to alkenes is called what?

A

Hydration

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131
Q

Describe hydration

A

An alkene will not react with pure water alone. If a small amount of strong acid catalyst is added an addition reaction takes place to yield an alcohol

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132
Q

Practice hydration example with Markovnikov’s rule

A

draw

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133
Q

What is an aromatic ring?

A

The class of compounds containing benzene like rings

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134
Q

Are benezene and other aromatic compounds reactive?

A

Much less than alkenes and don’t normall undergo addition reactions

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135
Q

What is benzene?

A

A flat, symmetrical molecule with with the molecular formula C6H6. Each carbon carbon alternates between a single and double bond (resonance)

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136
Q

Describe resonance

A

The phenomenon where the true structure of a molecule is an average among two or more conventional lewis structures that only differ in the placement of double bonds

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137
Q

Is a number needed for benzene?

A

No, all ring positions are identical

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138
Q

What are these examples of? Henzene, nitrobenzene

A

Benzene rings

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139
Q

Disubstituted benzines are unique in their naming, why?

A

Their place can be named differently, instead of 1,1 or 1,4 etc, it can be o- (ortho), m- (meta) and p- (para)C

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140
Q

Common name for methylbenzene

A

Toluene

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141
Q

Common name for hydroxybenzene

A

Phenol

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142
Q

Common name for aminobenzene

A

Aniline

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143
Q

The benzene ring itself may be considered a substituent group when attached to another parent compound. What is this called?

A

Phenyl

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144
Q

Draw the structure for m-chlorobutylbenzene

A

Draw

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145
Q

What is electrophilic aromatic substitution (EAS)?

A

A special type of substitution reaction that occurs for aromatic compounds

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146
Q

Nitration describe

A

The substitution of a nitro group (-NO2) for hydrogen on an aromatic ring

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147
Q

Halogenation (aromatic) describe

A

The substitution of a halogen group (-X) for hydrogen on an aromatic ring

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148
Q

What is sulfonation?

A

The substitution of a sulfonic acid group (-SO3H) for hydrogen on an aromatic ring

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149
Q

What is an alcohol?

A

Compounds that have a -OH group bonded to a saturated organic group R-O

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150
Q

What is a phenol?

A

Compounds that have an -OH group bonded directly to an aromatic benzene-like ring

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151
Q

What is an ether?

A

Compounds that have an oxygen atom bonded to two organic compounds R-O-R

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152
Q

Draw a ethyl alcohol

A

Draw

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153
Q

Draw a phenol

A

Draw

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154
Q

Draw a diethyl ether

A

Draw

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155
Q

Is there a structural similarity between alcohol and water?

A

Yes. In physical properties.Eg. bp for ethyl alcohol is 78.5° C vs water bp 100 °C

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156
Q

What is the high bp of ethyl alcohol and water due to?

A

Hydrogen bonding

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157
Q

Do hydrogen bonds form between alcohol molecules

A

Yes

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158
Q

Draw Isopropyl

A

Draw

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159
Q

Draw ethyl alcohol

A

Draw

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160
Q

Draw butyl alcohol

A

Draw

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161
Q

Naming alcohols

A
  1. Name parent
  2. Number carbons in chain
  3. Write name
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162
Q

How to name a a cyclic alcohol

A

cyclo–anol eg. cyclopentanol

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163
Q

How to name a cyclic alcohol

A
  1. Start numbering with carbon that bears the -OH group
  2. Give substituents the lowest possible numbers
164
Q

Name for alcohols with two hydroxy groups in the same molecule

A

Diols

165
Q

What is a glycol?

A

Diol with two -OH group on adjacent carbons (reserved for two compounds ethylene glycol and propylene glycol) - draw.

166
Q

Alcohols can be classified as primary secondary and tertiary according to what?

A

The number of carbon substituents bonded to the hydroxyl-bearing carbon

167
Q

Draw a primary, secondary, or tertiary alcohol

A

Draw

168
Q

Draw the structure of 2,3-dimethy-2-butanol. Classify the type of alcohol

A

Draw

169
Q

Draw the structure of 3-ethylcyclopentanol. Classify the type of alcohol.

A

Draw

170
Q

Are alcohols polar or nonpolar, why?

A

Polar, electronegativity of oxygen

171
Q

What has a strong influence on alcohol properties?

A

Hydrogen bonding

172
Q

How many straight-chain alcohols are liquid

A

Those up to 12 carbons

173
Q

What alcohols are miscible with water and can dissolve small amounts of ionic compounds

A

Ethanol and methanol

174
Q

Are methanol and ethanol miscible with organic solvents?

A

Yes

175
Q

Do alcohols have a hydrophobic and hydrophilic part?

A

Yes

176
Q

Property of alcohol

A

Alcohols with two or more -OH groups can form one hydrogen bond. They are therefore higher boiling and more water-soluble than similar alcohols with one -OH groups

177
Q

Describe dehydration

A

Alcohols undergo loss of water on treatment with strong acids. The reaction is driven to completion by heating. The -oh group is lost from one carbon and an -H is lost from an adjacent carbon to yield an alkene

178
Q

When more than one alkene can result a mixture of products is formed, true or false?

A

True

179
Q

Does the major product in alcohol have a greater number of alkyl groups directly attached to the double-bond carbons

A

Yes

180
Q

What products would you expect from a dehydration reaction, what is major, and what is minor?

A

Draw

181
Q

Which alcohol yields 4-methyl-2-hexene on dehydration?

A

Draw major and minor

182
Q

Describe oxidation

A

Occurs when primary and secondary alcohols are converted into carbonyl-containing compounds by an oxidizing agent

183
Q

What is a carbonyl group?

A

A carbon attached to an oxygen by a double bond

184
Q

Organic chemistry definition for organic oxidation

A

One that increases the number of C-O bonds and/or decreases the number of C-H bonds

185
Q

Organic chemistry definition for organic reduction

A

One that decreases the number of C-O bonds and/or increases the number of C-H bonds

186
Q

Primary alcohols are converted into what under controlled conditions?

A

Aldehydes

187
Q

Primary alcohols are converted to what if excess of oxidant is used

A

Carboxylic acid

188
Q

Secondary alcohols are converted into what on treatment with oxidizing agents

A

Ketones

189
Q

Do tertiary alcohols react with oxidizing agents?

A

No, because they do not have a hydrogen on the carbon atom to which the -OH group is bonded. Results in “No reaction”

190
Q

Properties of phenols

A

Influenced by the electronegative oxygen and hydrogen bonding

Most phenols are somewhat water-soluble and have higher melting and bp than similar alkylbenzenes

They are less soluble in water than alcohols

191
Q

Phenols are usually names with what ending (instead of benzene)

A

-phenol. Eg. p-Chlorophenol

192
Q

Many biomolecules contain a hydroxyl-substituted benzene ring

A

Draw tyrosine and eugenol

193
Q

Acidity of alcohols and phenols

A

Alcohols and phenols are weakly acidic because of the positively polarized -OH hydrogen. They dissociate slightly in solution and establish equilibria between neutral and anionic forms

194
Q

An alkoxide ion or anion of an alcohol is as strong a base as a hydroxide ion. How can alkoxide ions be produced?

A

By reacting an alcohol with a strong base or by reaction of an alkali metal with an alcohol

195
Q

Acidity of alcohols and phenols

A

Phenols are about 10,000 times more acidic than water. A phenoxide ion is produced by the reaction of a phenol with dilute aqueous sodium hydroxide

196
Q

What is an ether?

A

Compounds with two organic groups bonded to the same oxygen atom.

197
Q

How are ethers named?

A

By identifying the two organic groups and adding the word ether

198
Q

Cyclic esters are often referred to by their common names

A

Epoxide (ethylene oxide)
Tetrahydrofuran
1,4-Dioxane

199
Q

An -OH group is referred to as what

A

Alkoxy group

200
Q

Draw dimethoxyethane

A

Draw

201
Q

Describe an ether

A

Ethers are found throughout the plant and animal kingdoms. Some are present in plant oils and are used in perfumes; others have a variety of roles.

202
Q

Draw the structure for 3-methoxy-2-butanol

A

Draw

203
Q

What do skunks repel with horrible odors as with garlic and onion, what is this caused by?

A

Thiols

204
Q

Thiols describe

A

Also called mercaptans, compounds that contain an -SH group

205
Q

What is added to make leak detection easy due to natural gas being odorless

A

Methanethiol

206
Q

Thiols react with mild oxidizing agents to yield what?

A

Disulfides. Two thiols join in this reaction the hydrogen from each is lost, and a bond forms between the sulfurs

207
Q

Where do thiols come from?

A

Amino acid cysteine which is part of many proteins

208
Q

The proteins in hair are usually rich in S-S and S-H groups

A

Know

209
Q

True or false. A permanent wave results when disulfide bridges are formed between -SH groups in hair protein.

A

True

210
Q

What are the simplest halogen-containing compounds?

A

Alkyl halides, RX.. F Cl Br I

211
Q

Draw methyl bromide

A

Draw

212
Q

Draw ethyl bromide

A

Draw

213
Q

Draw phenyl bromide

A

Draw

214
Q

Describe aryl halides

A

Compounds that have an aromatic group bonded to a halogen atom, Ar - X

215
Q

Describe stereochemistry

A

The study of the relative three-dimensional spatial arrangement of the atoms in a molecule

216
Q

Stereochemistry

A

Mirror planes

217
Q

What are stereoisomers

A

Isomers that have the same molecular and structural formulas but different spatial arrangements of their atoms

218
Q

Can stereoisomers be converted into one another through rotation?

A

No.

219
Q

How to remember stereoisomers

A

They have handedness. Cannot be placed directly on top as they won’t align.

220
Q

When does chirality occur

A

When an object lacks symmetry. Without a plane of symmetry is achiral

221
Q

Chiral carbon atom

A

A carbon atom that is both tetrahedral and has four different groups attached to it

222
Q

Enantiomers / optical isomers

A

The two mirror images forms a chiral molecule like 2-butanol

223
Q

Are enantiomers a type of stereoisomer?

A

Yes

224
Q

Properties of pairs of enantiomers

A

Have many of the same physical properties, same melting point, solubility in water, isoelectric point, and density

225
Q

How do pairs of enantiomers differ?

A

In their biological activity, odors, and tastes, their effect on polarized light

226
Q

One enantiomer will rotate one way, the other a different way. What are these?

A

One enantiomer rotates the light to the right and is called the d or + enantiomer. The other will rotate the light to the left by exactly the same amount and is called the I or - enantiomer.

227
Q

Who is credited with the discovery of enantiomers?

A

Emil Fischer

228
Q

Most importantly, how do pairs of enantiomers differ

A

As drugs

229
Q

Practice determining which carbons may be chiral

A

Practice

230
Q

A carbonyl compound is any compound that contains what

A

C = O - carbonyl group

231
Q

What group does each of these belong to?

Acetaldehyde
Acetone
Acetic acid
Methyl acetate
Acetamide

A

Aldehyde
Ketone
Carboxylic acid
Ester
Amide

232
Q

Why are carbonyl groups strongly polarized

A

Oxygen is more electronegative than carbon

233
Q

What gives rise to the reactivity of the carbonyl group

A

The polarity

234
Q

Bond angles between the three substituents on the carbonyl carbon atom

A

120°

235
Q

Do aldehydes and ketones have similar or different properties?

A

Similar

236
Q

Why do aldehydes and ketones have similar properties?

A

Because their carbonyl groups are bonded to carbon and hydrogen atoms that do not attract electrons strongly

237
Q

What is an aldehyde?

A

A compound that has a carbonyl group bonded to at least one hydrogen, always ends in carbon chain

238
Q

What is a ketone?

A

A compound that has a carbonyl group bonded to two carbons in organic groups that can be the same or different, always within a carbon chain (not end)

239
Q

Draw the line structure for 1-phenylpropanone

A

Draw

240
Q

Draw the line structure for 1-cyclohexyl-3,3-dimethyl-2-butanone

A

Draw

241
Q

Are aldehydes and ketones polar or non-polar

A

Polar (moderately) - due to the presence of carbonyl group

242
Q

Why do aldehydes and ketones have lower boiling points than alcohols but higher boiling points than alkanes

A

Dipole-dipole interactions

243
Q

What are common aldehydes and ketones usually (gas, liquid, solid?)

A

Liquids

244
Q

Many aromas and flavors derive largely from what?

A

Naturally occurring aldehydes and ketones

245
Q

Formaldehyde properties

A

Toxic.
At room temp, a colorless gas with a pungent suffocating odor.

Low concentrations in the air can cause eye throat and bronchial irritation and higher concentrations that can trigger asthma attacks

Skin contact can produce dermatitis.

Formaldehyde is commonly sold as 37% aqueous solution under the name formalin

It kills viruses, fungi, and bacteria by reacting with amino groups in proteins allowing for its use in disinfecting and sterilizing equipment

246
Q

Properties of acetaldehyde

A

Sweet-smelling but narcotic
flammable liquid formed by the oxidation of ethyl alcohol

hangover smell alcohol breakdown in the body produces acetaldehyde

large doses can cause respiratory failure

It is most commonly used for the preparation of polymeric resins, in organic synthesis, and in the silvering of mirrors

247
Q

Properties of Acetone

A

Most widely used of all organic solvents, dissolves most organic compounds, and also is miscible with water.

Volatile and is a serious fire and explosive hazard when allowed to evaporate in a closed space

No chronic health risk has been associated with casual acetone exposure

When the breakdown of fats and carbohydrates is out of balance, acetone is produced in the liver

248
Q

Properties of Benzaldehyde

A

A colorless liquid, pleasant almond or cherry odor, first extracted from bitter almonds

Used as a flavoring and fragrance in food, cosmetics, pharmaceuticals, and soap is generally regarded as safe by the FDA.

Used industrially as a forerunner to other organic compounds ranging from pharmaceuticals to plastic additives

249
Q

What is replaced during aldehyde oxidation

A

The hydrogen bonded to the carbonyl carbon is replaced by an -OH group

250
Q

Do ketones react with oxidizing agents?

A

They do not have this hydrogen so they do not react cleanly.

251
Q

Can aldehydes be reduced?

A

Yes to primary alcohols

252
Q

Can ketones be reduced?

A

Yes to secondary alcohols

253
Q

How do reductions occur - ketones and aldehydes

A

By formation of a bond to the carbonyl carbon by a hydride ion: H- accompanied by bonding of a hydrogen ion H+ to the carbonyl oxygen atom

254
Q

A – ion has a lone pair of valence electrons. Both electrons are used to form a covalent bond to the carbonyl carbon

A

Hydride..

A negative charge is left on the carbonyl oxygen. Aqueous acid is then added, H+ bonds to the oxygen, and a neutral alcohol results

255
Q

UP TO SLIDE 95

A

When this reaction takes place with an aldehyde, the product is called a ‘hemiacetal’; and when this reaction takes place with a ketone, the product is referred to as a ‘hemiketal’.

256
Q

Aldehydes undergo addition reactions in which an alcohol combines with what?

A

The carbonyl carbon and oxygen

257
Q

What is the additional product of additional reactions for alcohols?

A

Hemaicetals

258
Q

What is a hemiacetal?

A

Have both an alcohol-like group - OH and an etherlike group -OR bonded to what was once the carbonyl carbon atom

259
Q

How are hemiacetals formed?

A

From the carbonyl-group oxygen and the OR from the alcohol bonds to the carbonyl-group carbon

260
Q

Differentiate hemiacetals and hemiketals

A

When this reaction takes place with an aldehyde, the product is called a ‘hemiacetal’; and when this reaction takes place with a ketone, the product is referred to as a ‘hemiketal’.

261
Q

Can hemiacetals revert to aldehydes or ketones?

A

Yes! Through the loss of alcohol and establish an equilibrium with the aldehyde or ketone

262
Q

Hemiacetal formation are they stable or not? whats the major exception?

A

Often too unstable to be isolated, a major exception occurs when the -OH and CHO functional groups that react are part of the same molecule

263
Q

Acetal formation

A

Hemiacetals can react with a second alcohol molecule to form an acetal.

264
Q

What is an acetal?

A

A compound that has two etherlike groups bonded to what was the carbonyl carbon atom

265
Q

Acetal hydrolysis describe

A

A reaction in which a bond or bonds are broken and the H- and -OH of water add to the atoms of the broken bond or bonds

266
Q

What is acetal hydrolysis?

A

This is the reversal of acetal formation, it requires an acid catalyst and a large quantity of water to drive the reaction back toward the aldehyde or ketone

267
Q

What is written above the arrow for acetyl hydrolysis?

A

Acid catalyst

268
Q

What does an amine contain?

A

One or more organic groups bonded to nitrogen

269
Q

Amines

A

When a nitrogen atom in an amine has three bonds it will have a non-bonding electron pair. This is called a free amine and the nitrogen will have a neutral charge. When a fourth bond is formed at the nitrogen the product is an ammonium ion

270
Q

How to name primary alkyl amines

A

Named by identifying the alkyl group attached to nitrogen and adding the suffix- amine to the alkyl group name eg. ethylamine or isopropylamine

271
Q

Do simple secondary and tertiary amines have identical or different alkyl groups?

A

Identical

272
Q

What to do when the R groups in secondary or tertiary amines are different?

A

Name these amines as N-substituted derivatives of a primary amine. Identify the parent chain and then treat all other alkyl groups as N-substituent

273
Q

Draw the structure of N,N-diethylbutylamine

A

Draw

274
Q

What is the -NH2 functional group?

A

Amino group

275
Q

The simplest aromatic amine is known as what?

A

Aniline

276
Q

What is responsible for many properties of amines?

A

The lone electron pair on the nitrogen as well as electronegativity difference between N and H are responsible for many of the properties of amines

277
Q

What causes amides to act as lewis bases

A

Nonbonding electron pair

278
Q

What is a Lewis base?

A

A compound containing an unshared pair of electrons

279
Q

What type of amines can hydrogen bond with one another and with water?

A

Primary and secondary amines

280
Q

Properties of amines (1° and 2°)

A

Higher bp than alkanes of similar size. Oxygen can form more hydrogen bonds per molecule than nitrogen; alcohols have even higher boiling points than amines

281
Q

Amines with up to how many carbons have appreciable solubility in water due to hydrogen bonding?

A

6

282
Q

What functional group is this associated with? Some volatile – have strong odors. Some smell like ammonia and others like stale fish or decaying meat

A

Amines

283
Q

What type of amines are irritating to the skin, eyes, mucous membranes and are toxic by ingestion?

A

Simpler amines

284
Q

What types of amines are isolated from various plants and can be very poisonous?

A

Complex amines

285
Q

Heterocycle describe

A

A ring that contains nitrogen or some other atom in addition to carbon. In many nitrogen-containing compounds, the nitrogen atom is in a ring with carbon atoms

286
Q

Why are aqueous solutions of amines weakly basic?

A

Because of the formation of -OH and R3NH+ ions in water

287
Q

What happens when an amine is pronated?

A

It’s electron pair will become positively charged (called ammonium ion)

288
Q

What is the conjugate acid of an amine?

A

Ammonium ion, will form whenever an amine is in water or in the presence of an acid

289
Q

In a acidic aqueous solution, what is the acidic species?

A

H3O+. Hydronium will donate a proton to an amine forming an ammonium ion.

290
Q

When amines act as bases, what do ammonium ions act as?

A

Weak acids

291
Q

What happens with ammonium ions with bases?

A

The amine can be regenerated

292
Q

True or false. In physiological conditions, the aqueous environment of the blood and other bodily fluids contain amines in their pronated state as ammonium ions

A

True

293
Q

What is an alkaloid?

A

A naturally occurring nitrogen-containing compound isolated from a plant or animal usually basic, bitter and poisonous

294
Q

The bitterness and poisonous nature of this likely protects plants from being devoured by animals

A

Alkaloids

295
Q

Describe atropine

A

The toxic tropane alkaloid is found in deadly nightshade or belladonna. Acts on the CNS by blocking acetylcholine a property applied in medications to reduce cramping of the digestive tract. Also used as an antidote against nerve gases such as sarin which causes the build-up of acetylcholine

296
Q

Describe Ergotamine

A

An alkaloid produced by the ergot fungus which grows on rye. Common in Middle Ages, usually used medicinally as treatment for migraines, as oxytocic treatment for Parkinsons’ and dementia

297
Q

How many alkaloids are present in the poppy?

A
  1. Incl. morphine and codeine.
298
Q

What type of compound contains a carbonyl group bonded to an electronegative heteroatom?

A

Type 2

299
Q

Carboxylic acid describe

A

Have an -OH group bonded to the carbonyl group

300
Q

Describe esters

A

Have an -OR group bonded to a carbonyl carbon (R - C=O (above not linear) - OR)

301
Q

Abbv. for esters

A
  • CO2R
302
Q

What group do amides have bonded to the carbonyl carbon?

A

-NH2, -NHR OR -NR2(amino group)

303
Q

How are amides classified?

A

Based on the substitution of the nitrogen atom position and how many R groups show the classification, 1 = primary, 2 = secondary, 3 = tertiary amide

304
Q

Properties of carboxylic acids

A

Weakly acidic - pKa ~5
The carboxylic hydrogen atom is transferred in acid-based reactions
Conjugate base = ‘carboxylate anion’
Like alcohols, C.A’s can form H+ bonds with each other
Many are water soluble and have high mp/bp points

305
Q

C. acids features

A

Acids with saturated unbranched R groups of up to nine carbon atoms are liquids. Those with up to 4 carbons are water-soluble. Acids with larger saturated R groups are waxy-odorless solids

306
Q

C. acids undergo what type of reactions most commonly? explain

A

Carbonyl-group substitution reactions in which a group we represent as -Z relaces the group bonded to the carbonyl carbon atom.

307
Q

Naming for c. acids

A

Normal rules. Identified by Greek letters though , a , b, y, and so on rather than numbers

308
Q

Dicarboxylic acid describe

A

Contain two - COOH groups and are names systemically by adding the ending -dioic acid to the alkane name

309
Q

Unsaturated acids are named with “-enoic” - different to saturated which is anoic

A

Enoic = double bond
Anoic = single bonds
(C = O disregarding this double bond)

310
Q

Can esters be convertyed back to C. acids? if yes how

A

Yes. Through hydrolysis

311
Q

Ethyl Ester boling point compared to acetic acid and methyl ester

A

Acetic = 118° C
Methyl ester = 57° C
Ethyl ester = 77° C

312
Q

What do esters have that is different that they “contain” within their structures?

A

Parent carboxylic acid and alcohol. Esters have two words in their name, alkyl group is derived from the alcohol component, second is the name of the parent acid wiht the ending replaced by -ate.

313
Q

Example of ester naming ethyl acetate

A

The first part is acetic acid, second is ethyl alcohol

314
Q

Amide description

A

Compounds with nitrogen directly attached to the carbonyl carbon atom are amides

315
Q

What amides are soluble in both water and organic solvents?

A

Unsubstituted amides with low molecular weight

316
Q

Describe hydrogen bonding for monosubstituted amides and disubstituted amides

A

Monosubstituted amides can also form hydrogen bonds to each other, disubstituted amides cannot do so and are therefore lower boiling

317
Q

Difference between amides and amines

A

The nitrogen atom is bonded to a carbonyl group carbon in an amide but not an amine

318
Q

In an amide, the nitrogen atom may have an alkyl substituent in it. How is this names?

A

Specifying the alkyl substituents and the amide name. The alkyl substituents are preceded by the letter N to identify them as being attached directly to nitrogen

319
Q

The portion of the carboxylic acid that does not change during a carbonyl group substitution reaction is known as what?

A

Acyl group

320
Q

The acyl group that remains when a c.acid loses its -OH is named by replacing the -ic at the end of the acid with what?

A

-oyl

321
Q

Exception for acyl group from acetic acid is called what?

A

Acetyl group

322
Q

What is a carboxylate anion?

A

The anion that results from the ionization of a carboxylic acid

323
Q

What reaction do c.acids undergo?

A

Neutralization

324
Q

C.acids undergo neutralization to form what?

A

Carboxylic acid salt and water

325
Q

Describe esterification

A

Carried out by warming a carboxylic acid with an alcohol in the presence of a strong-acid catalyst eg. sulfuric acid (rxns often reversible and reach equilibrium with equal parts of both reactants and products present).

326
Q

How are amides formed?

A

By the acylation of amines. Acylation of an amine involves the replacement of the N-H bond with an acyl group.

327
Q

Primary amide formation

A

A process where unsubstituted amides are formed by the reaction of c.acids with ammonia

328
Q

Secondary amide formation

A

Secondary amides are formed by the reaction of a carboxylic acid and a primary amine

329
Q

Tertiary amine formation

A

Tertiary amides are formed by reaction of carboxylic acid and a secondary amine

330
Q

What happens when a tertiary amine reacts with a carboxylic acid?

A

Tertiary amines do not have an N-H bond and are more sterically hindered. Instead of performing a substitution they react as bases instead

331
Q

What process do esters and amides undergo to give back c.acids plus alcohols or amines?

A

Esters and amines

332
Q

Hydrolysis of esters

A

Substitution reaction

R - (C = O) - OR + H - OH –> R - (C = O) - OH + O - OR

333
Q

Hydrolysis of amides

A

R - (C=O) - N - R (x2) + H - OH –> R - (C = O) - OH + H - N - R(x2)

334
Q

What does acid-catalyzed hydrolysis do?

A

Reverse esterification

335
Q

Ester hydrolysis using a base such as NaOH or KOH is known as what?

A

Saponification

336
Q

Amide hydrolysis properties

A

Amides are stable in water, but hydrolyze with heating in the presence of acids or bases

337
Q

Phosphate ester

A

A compound formed by the reaction of an alcohol with phosphoric acid

338
Q

Possible diester and triesters

A

Dimethyl phosphate (phosphate diester) and trimethyl phosphate (phosphate triester)

339
Q

Are phosphate monoesters diesters basic or acidic?

A

Acidic as they contain acidic hydrogen atoms. In neutral or alkaline solutions they are ions.

340
Q

How is diphosphoric and triphosphoric acid formed?

A

By two or three molecules of phosphoric acid combine to lose water. The collective name is called anhydrides.

341
Q

The PO3 2- group is part of a larger molecule known as what?

A

Phosphoryl group

342
Q

What is the transfer of a phosphoryl group from one molecule to another called

A

Phosphorylation

343
Q

In biochem, phosphoryl groups are provided by ATP which is converted to an ADP in a reaction accompanied by what?

A

The release of energy

344
Q

Definition of biochemistry

A

The study of molecules and their reactions in living organisms

345
Q

Where is the word protein from?

A

Greek language, means primary.

346
Q

What is a protein?

A

A description for the biological molecules that are of primary importance to all living organisms

347
Q

What roles do proteins play in living things?

A

Structural: They provide structure - keratin, actin throughout our bodies
Hormones: Signalling molecule/protein
Catalyst: Molecular machinery
Storage and transport
Immunity

348
Q

Proteins are polymers of what?

A

Amino acids

349
Q

What do all amino acids contain?

A

An amine group, a carbonyl group and an R group called a side chain bonded to a central carbon atom

350
Q

How can amino acids be drawn?

A

Neutral form or in ionized form Zwitterion

351
Q

How many amino acids are there

A

20

352
Q

How many letters in an amino acid code

A

3

353
Q

For how many of these amino acids has the only identity of the side chain attached to the carbon differing

A

19

354
Q

What amino acid is a secondary amine whose nitrogen and carbon ring are joined in a 5 membered rin

A

Proline

355
Q

Non-polar A.A

A

Glycine, alanine, valine, proline, leucine, isoleucine, methionine, tryptophan, and phenylalanine (all are hydrophobic)

356
Q

Polar A.A

A

Serine, threonine, tyrosine, asparagine, glutamine, cysteine

357
Q

A.A with positve charge

A

Lyesine, Arginine, Histidine

358
Q

A.A with negative charge

A

Aspartic acid, glutamic acid

359
Q

Forces present between amino acids are called what?

A

Intermolecular

360
Q

Types of intermolecular forces present between amino acids or between proteins are called what?

A

H-bonding, London dispersion forces, Ionic bonding, Disulfide bonds

361
Q

Non-polar side chains on amino acids are described as what

A

hydrophobic

362
Q

What strategy is used to avoid aqueous fluids?

A

Nonpolar side chains gather into clusters to create a water-free environment

363
Q

What regions in a protein are hydrophilic (water-loving)

A

The polar, acidic , and basic side chains

364
Q

How many of the common amino acids are chiral?

A

19

365
Q

What is the only achiral amino acid?

A

Glycine

366
Q

Nature only selects what form of amino acids for making proteins?

A

L-amino acids

367
Q

What is zwitterion

A

A neutral dipolar ion that has one positive charge and one negative charge

368
Q

Amino acids contain two groups, what are they?

A

Acidic group - COOH and basic group - NH2. These two groups can undergo an intramolecular acid base reaction to form a zwitterion

369
Q

Amino acids have the characteristics of what?

A

Salts

370
Q

The zwitterion can either pronate or accept a proton depending on what?

A

The pH of the environment

371
Q

In a basic environment, the ammonium will – a proton to the base?

A

Donate

372
Q

In an acidic environment the carboxylate will – a proton from the acid

A

Accept

373
Q

Isoelectric point (pI) describes what?

A

The pH at which a sample of an amino acid has equal numbers of positive and negative charges. Here the net charge of all molecules in a pure sample is 0.

374
Q

Is the pI for each amino acid different? if so why?

A

Yes, due to the influence of the side-chain

375
Q

Why are side-chain interactions important? in amino acids

A

To stabilize a protein structure. It is important to be aware of charges at physiological pH.

376
Q

What does the isoelectric point influence?

A

Protein solubility and determine which amino acids in an enzyme participate directly in enzymatic reactions

377
Q

What is a peptide bond?

A

An amide bond that links two amino acids together

378
Q

How does a dipeptide result?

A

From the formation of a peptide bond between the -NH3+ group of one amino acid and the -COOH group of the second amino acid

379
Q

Does the sequence of amino acids in a peptide or protein chain matter?

A

Yes, the exact sequence. Variation can indicate a different molecule. Ala-Ser is not the same as Ser-AlA

380
Q

What is the peptide order rule

A

N -> C terminal amino acid

381
Q

What is at the N - N-terminus?

A

The free - NH3+ group

382
Q

What is at the C - Terminus?

A

The free -CO2H group on the right

383
Q

Individual amino acids joined in the chain are referred to as what?

A

Residues

384
Q

How is a peptide named?

A

By citing the amino acid residues in order, starting at the N-terminus and ending at the C-terminus

385
Q

What is the primary structure

A

The sequence of amino acids in a protein chain

386
Q

What is along the backbone of a protein?

A

A chain of alternating peptide bonds and a -carbon atoms

387
Q

How do the carbon and nitrogen atoms along the backbone lie

A

In a zigzag arrangement with tetrahedral bonding around the a-carbon atoms

388
Q

Primary protein structure 1st degree

A

Very crucial to function that the change of only one amino acid can drastically alter a protein’s biological properties

389
Q

What are the two hormones secreted by the pituitary gland differ in only two amino acids in the primary sequence?

A

Oxytocin, Vasopressin

390
Q

What does vasopressin do?

A

Regulates blood pressure, blood osmolality, and blood volume

391
Q

What does oxytocin do?

A

Known to stimulate uterine contractions in labor and childbirth to stimulate contractions of breast tissue to aid in lactation after child birth

392
Q

Interactions between the backbone of amino acid residues induces changes to the shape of the primary structure. What does this refer to?

A

Secondary structure

393
Q

What are the two kinds of repeating patterns in the secondary structure

A

Alpha helix and beta-sheet

394
Q

Alpha helix

A

A secondary protein structure in which a protein chain forms a right-handed coil stabilized by hydrogen bonds between peptide groups along the backbone

395
Q

Beta-sheet

A

A secondary protein structure in which adjacent protein chains either in the same molecule or in different molecules are held together by hydrogen bonds forming a flat sheetlike structure

396
Q

Proteins are classified in several ways which is to identify them as either – or –

A

Fibrous proteins or globular proteins

397
Q

Fibrous proteins

A

Tough, insoluble protein whose chains form fibers or sheets

398
Q

Globular protein

A

Water soluble proteins whose chains are folded in a compact shape with certain types of groups on the outside

399
Q

Tertiary proteins structure

A

The way in which an entire protein chain is coiled and folded into its specific three-dimensional shape.

400
Q

There are four forces responsible for the tertiary structure of a protein

A
  1. Hydrogen bonding
  2. Salt bridges (ionic)
  3. Hydrophobic interactions
  4. Hydrophobic interactions

also disulfide linkages

401
Q

Hydrogen bonding - proteins tertiary

A

Side chain hydrogen can connect different parts of a protein molecule whether they are in close proximity or far apart along the polypeptide chain

402
Q

Side chain - salt bridges in proteins tertiary

A

Where there are ionized acidic and basic side chains the attraction between their positive and negative charges creates salt bridges

403
Q

Hydrophilic - proteins tertiary

A

Amino acids with charged R groups will interact with water through hydrogen bonding

404
Q

Hydrophobic interactions - proteins tertiary

A

Hydrocarbon side chains are attracted to each other by dispersion forces (primarily van der waal forces) which can create a water-free pocket in the protein chain

405
Q

Covalent sulfur-sulfur bonds (disulfide bridge)

A

Cytestenine amino acid ress

Chem 102 (1 decks)

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