Final exam prep Flashcards
(405 cards)
1
Q
What are covalent bonds?
A
A way that elements can share electrons with others rather than transferring them
2
Q
Octet rule
A
Elements want eight valence electrons
3
Q
Lewis dot structure
A
Simplified structural representations of molecules that show bonding and non-bonding electrons
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
5
Q
What is organic chemisrtry
A
The study of carbon compounds
6
Q
Nature of carbon
A
Tetravalalent - always 4 bonds. Organic molecules have covalent bonds
7
Q
Atoms gain lose or share valence electrons to achieve noble gas configuration. true or false
A
T
8
Q
Can carbon form multiple covalent bonds?
A
Yes
9
Q
Draw a tetrahedral molecule
A
Draw
10
Q
Draw a trigonal planar molecule
A
Draw
11
Q
Draw a linear molecule
A
Draw
12
Q
Are all covalent bonds equivalent to each other?
A
No, due to electronegativity
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
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
15
Q
How can organic compounds be classified?
A
In their functional groups
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
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
18
Q
What are the functional groups that are also hydrocarbons?
A
Alkanes, alkenes, alkynes, simple aromatic compounds
19
Q
Describe an alkane
A
Alkanes have single bonds and contain no functional group. Example octane, cyclohexane
20
Q
Describe an alkene
A
Alkenes have a carbon-carbon double-bond functional group. Example retinol, butene
21
Q
Describe an alkyne
A
Alkyne has a carbon-carbon triple bond.
22
Q
Describe a simple aromatic compound
A
Simple aromatic compounds contain a six-member ring of carbon atoms wit three alternating double bonds.
23
Q
Describe an alkyl halide
A
Have a carbon-halogen bond
24
Q
Describe an alcohol
A
Carbon is bonded to an -OH group
25
Describe an ether
Have two carbons bonded to the same oxygen
26
Describe an amine
Have a carbon bonded to an -NH2 group (draw)
27
How are amines and amides different?
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.
28
Draw an aldehyde
Draw
29
Draw a ketone
Draw
30
Draw a carboxylic acid
Draw
31
Draw an ester
Draw
32
Draw an amide
Draw
33
Draw a anhydride
Draw
34
Three functional groups contain sulfur. Name them..
Thioalcohols (thiols), sulfides and disulfides
35
Draw and identify which functional group this has: C2H7N
Amine
36
Draw and identify which functional group this has: C3H4
Alkyne
37
Draw and identify which functional group this has: C4H10O
Ether
38
What forms the "backbone" of a compound
The carbon atoms bonded together with the hydrogens on the periphery
39
What is the general formula for acylic alkanes?
CnH2n+2
40
Describe an isomer
Compounds that have the same molecular formula but different structural formulas
41
Draw the 2 isomers for C4H10
Draw
42
What is a straight-chain alkane?
Alkane that has all its carbons connected in a row
43
What is a branched chain alkane?
An alkane that has a branching connection of carbons
44
What is a constitutional isomer?
Compounds with the same molecular formula but with different connections among their atoms. Also known as structural isomers.
45
How are constitutional isomers different from their 'non-isomer form'
They are chemically distinct from their 'simple format - the non-isomer version' and often have different structures and different
46
What is a functional group isomer?
When the molecular formula contains atoms other than carbon and hydrogen the constitutional isomers obtained can also be functional group isomers
47
Draw C3H8O as a single line, a structural isomer, and also as a functional group isomer
3 drawings, label
48
Draw all the isomers that have the formula C6H14
Draw 5 isomers!
49
Condensed structure, what is it?
A shorthand way of drawing structures which C-C and C-H bonds are understood rather than shown
50
Draw the full and condensed formula for butane
Draw
51
Draw the full and condensed formula for 2-methylpropane
Draw 2
52
Draw the line structure for C4H10
Draw
53
True or false: most carbon atoms in an alkane have its four bonds pointing toward the four corners of a tetrahedron
False, it is all carbons.
54
Various conformations of a molecule are called what?
Conformers
55
Describe a conformer
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
56
Do molecules prefer to be the least crowded lowest energy extended conformation or not?
Yes, they do prefer this. They don't want to be spatially close
57
Look at conformers and draw some out.
Draw
58
Who invented the system of naming in organic chemistry?
IUPAC (international union of pure and applied chemistry).
59
How are carbon atoms classified?
Based on how many other carbon atoms are attached. Degree of substitution
60
How many "Parts" does a molecule have
The parent and substituent groups
61
Name the prefix for carbons 1-10
Meth, Eth, Prop, But, Pent, Hex, Hept, Oct, Non, Dec
62
Name the suffix for all functional groups
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
63
Draw the 4 possibilities for 4 carbon structure
Butyl, sec-butyl, isobutyl, text-butyl
64
Steps to naming branched chain alkanes
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
65
Properties of alkanes
Only non-polar C-C bonds and C-H bonds. Only forces are weak intermolecular and these are influenced by weak London dispersion forces
66
Trend with alkanes boiling point and melting point
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.
67
Why is there a trend with alkanes and boiling point?
London dispersion forces
68
What is it called when alkanes react with oxygen?
Combustion
69
What is it called when alkanes react with halogens
Halogenation
70
Describe combustion
An oxidation reaction that commonly takes place in a controlled manner in an engine or furnace
71
What are the products of complete combustion?
Carbon dioxide and water (and a large amount of heat is released)
72
Describe halogenation
Is the replacement of an alkane hydrogen by a chlorine or bromine initiated by heat or light
73
What is free radical halogenation associated with?
Halogenation
74
What is released during complete combustion
Heat - large amount
75
How many H's are released at a time in halogenation? Why?
1, as if it was able to do more then they would all be replaced with halogens
76
What does complete chlorination of methane yield?
Carbon Tetrachloride
77
What is the placement of what goes above and below the arrow in chemistry?
Reactants and reagents above, solvents and catalysts below
Eg. Br2 above, light and heat below.
78
Draw 2-methyl butane with bromine
2-bromo-2-methylbutane
79
What is a cycloalkane?
An alkane that contains a ring of carbon atoms
80
For a cycloalkane, to form a closed ring it requires what?
An additional C-C bond and the loss of 2H atoms. Eg. C6H14 and cyclohexane (now C6H12)
81
General formula for cycloalkane
CnH2n
82
What are the bond angles in cyclopropane?
60°
83
What are the bond angles in cyclobutene?
90°
84
Are 5 and 6-carbon rings more or less stable than a ring with fewer carbons?
More stable
85
Are cyclopentane and cyclohexane stable?
Yes
86
Describe the properties of cycloalkanes
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.
87
Naming cycloalkane steps
1. Use the cycloalkane name as the parent
2. Identify and number substituents
88
Draw a line structure for 1,3-dimethylcyclohexane
Draw (2 options)
89
Draw a line structure for 1-(sec-butyl)-4-isopropylcyclohexane
Sec = secondary (to note)
90
Are alkanes saturated?
Yes they have as many hydrogens as possible
91
Are alkenes and alkynes saturated or unsaturated?
Unsaturated. They contain carbon-carbon multiple bonds
92
Naming cycloalkenes
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
93
Common name for ethene
Ethylene
94
Common name for propene
Propylene
95
Common name for 2-methyl-1,3-butandiene
Isoprene
96
Common name for ethyne
Acetylene
97
Draw the strucutre for 3-ethyl-4-methyl-2-pentene
Draw
98
What causes alkenes and alkynes to differ in shape
The presence of multiple bonds
99
Is there rotation around a C=C double bond?
No - bond is rigid.
100
What is a cis isomer?
When two groups are on the same side of a double bond. eg. cis-2-butene
101
What is a trans isomer?
When two groups are on opposite sides of a double bond. Eg. trans-2-butene
102
Draw the structure for both the cis and trans isomers of 2-hexene
Draw
103
Properties of alkenes and alkynes
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.
104
What are the four main types of organic reactions?
Addition
Elimination
Substitutions
Rearrangements
105
What is an addition reaction?
Involves taking two molecules and combining them together.
106
What type of organic reaction is hydrogenation?
Addition (addition of an alkene with hydrogen to make an alkane)
107
What is an elimination reaction?
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.
108
The elimination of water from an alcolhol forms what?
An alkene (ethylene)
109
What is a substitution reaction?
One atom (or group of atoms) is replaced by another atom (or group of atoms) on a substrate molecule.
Eg. AB + C --> AC + B
110
What type of reaction is the halogenation of an alkane?
Substitution
111
Describe a rearrangement reaction
Involves the bonds and atoms on a molecule reorganizing. Atoms moving from one location to another. Bonds shifting from one location to another.
112
Is cis-trans isomerism an example of a rearrangement reaction
Yes
113
What type of reaction is an alkene to an alkyne typically?
Addition
114
A reagent can be added to the multiple bond to yield a saturated product. What type of bonds will the product now have?
Single bonds only
115
What do these involve the addition of? Hydrogenation, halogenation, hydrohalogenation, hydration?
Hydrogenation: H2
Halogenation: Cl2 or Br2
Hydrohalogenation: H-Cl or H-Br
Hydration: H-OH
116
What is the addition of H2 to alkenes and alkynes called?
Hydrogenation. Also needs a metal catalyst to yield an alkane
117
How can hydrogenation be shown in a lab?
Using a balloon and an adaptor
118
Addition reaction of alkene example
An industrial hydrogenation reactor is designed to operate at higher pressure
119
Describe hydrogenation
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!).
120
The addition of Cl2 and Br2 to alkenes and alkynes is halogenation. Specifically for alkenes and alkynes what does this produce?
1,2-dihaloalkane addition products
121
What is a common halogen that can be used as a test for multiple bonds and unsaturation of fats?
Bromine
122
What is the addition of HBr and HCl to alkenes?
Hydrohalogenation
123
What do alkenes react with to yield alkyl bromides
Hydrogen bromide
124
What do alkenes react with to yield alkyl chlorides?
Hydrogen chloride
125
Draw the addition of HBr to 2-methylpropene
Draw
126
What is Markovnikov's rule and what does it help us to predict?
This rule helps us to predict the major product arising from addition reactions such as hydrohalogenation. It predicts where the X goes.
127
Markovnikov's rule says that the hydrogen atom attaches where?
To the carbon with more H-atoms
128
Markovnikov's rule says that the X attaches where?
To the carbon with fewer H-atoms
129
What happens if an alkene has equal numbers of H atoms attached to the double-bond carbons?
Both possible products are formed in approximately equal amounts.
130
The addition of water to alkenes is called what?
Hydration
131
Describe hydration
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
132
Practice hydration example with Markovnikov's rule
draw
133
What is an aromatic ring?
The class of compounds containing benzene like rings
134
Are benezene and other aromatic compounds reactive?
Much less than alkenes and don't normall undergo addition reactions
135
What is benzene?
A flat, symmetrical molecule with with the molecular formula C6H6. Each carbon carbon alternates between a single and double bond (resonance)
136
Describe resonance
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
137
Is a number needed for benzene?
No, all ring positions are identical
138
What are these examples of? Henzene, nitrobenzene
Benzene rings
139
Disubstituted benzines are unique in their naming, why?
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
140
Common name for methylbenzene
Toluene
141
Common name for hydroxybenzene
Phenol
142
Common name for aminobenzene
Aniline
143
The benzene ring itself may be considered a substituent group when attached to another parent compound. What is this called?
Phenyl
144
Draw the structure for m-chlorobutylbenzene
Draw
145
What is electrophilic aromatic substitution (EAS)?
A special type of substitution reaction that occurs for aromatic compounds
146
Nitration describe
The substitution of a nitro group (-NO2) for hydrogen on an aromatic ring
147
Halogenation (aromatic) describe
The substitution of a halogen group (-X) for hydrogen on an aromatic ring
148
What is sulfonation?
The substitution of a sulfonic acid group (-SO3H) for hydrogen on an aromatic ring
149
What is an alcohol?
Compounds that have a -OH group bonded to a saturated organic group R-O
150
What is a phenol?
Compounds that have an -OH group bonded directly to an aromatic benzene-like ring
151
What is an ether?
Compounds that have an oxygen atom bonded to two organic compounds R-O-R
152
Draw a ethyl alcohol
Draw
153
Draw a phenol
Draw
154
Draw a diethyl ether
Draw
155
Is there a structural similarity between alcohol and water?
Yes. In physical properties.Eg. bp for ethyl alcohol is 78.5° C vs water bp 100 °C
156
What is the high bp of ethyl alcohol and water due to?
Hydrogen bonding
157
Do hydrogen bonds form between alcohol molecules
Yes
158
Draw Isopropyl
Draw
159
Draw ethyl alcohol
Draw
160
Draw butyl alcohol
Draw
161
Naming alcohols
1. Name parent
2. Number carbons in chain
3. Write name
162
How to name a a cyclic alcohol
cyclo--anol eg. cyclopentanol
163
How to name a cyclic alcohol
1. Start numbering with carbon that bears the -OH group
2. Give substituents the lowest possible numbers
164
Name for alcohols with two hydroxy groups in the same molecule
Diols
165
What is a glycol?
Diol with two -OH group on adjacent carbons (reserved for two compounds ethylene glycol and propylene glycol) - draw.
166
Alcohols can be classified as primary secondary and tertiary according to what?
The number of carbon substituents bonded to the hydroxyl-bearing carbon
167
Draw a primary, secondary, or tertiary alcohol
Draw
168
Draw the structure of 2,3-dimethy-2-butanol. Classify the type of alcohol
Draw
169
Draw the structure of 3-ethylcyclopentanol. Classify the type of alcohol.
Draw
170
Are alcohols polar or nonpolar, why?
Polar, electronegativity of oxygen
171
What has a strong influence on alcohol properties?
Hydrogen bonding
172
How many straight-chain alcohols are liquid
Those up to 12 carbons
173
What alcohols are miscible with water and can dissolve small amounts of ionic compounds
Ethanol and methanol
174
Are methanol and ethanol miscible with organic solvents?
Yes
175
Do alcohols have a hydrophobic and hydrophilic part?
Yes
176
Property of alcohol
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
Describe dehydration
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
When more than one alkene can result a mixture of products is formed, true or false?
True
179
Does the major product in alcohol have a greater number of alkyl groups directly attached to the double-bond carbons
Yes
180
What products would you expect from a dehydration reaction, what is major, and what is minor?
Draw
181
Which alcohol yields 4-methyl-2-hexene on dehydration?
Draw major and minor
182
Describe oxidation
Occurs when primary and secondary alcohols are converted into carbonyl-containing compounds by an oxidizing agent
183
What is a carbonyl group?
A carbon attached to an oxygen by a double bond
184
Organic chemistry definition for organic oxidation
One that increases the number of C-O bonds and/or decreases the number of C-H bonds
185
Organic chemistry definition for organic reduction
One that decreases the number of C-O bonds and/or increases the number of C-H bonds
186
Primary alcohols are converted into what under controlled conditions?
Aldehydes
187
Primary alcohols are converted to what if excess of oxidant is used
Carboxylic acid
188
Secondary alcohols are converted into what on treatment with oxidizing agents
Ketones
189
Do tertiary alcohols react with oxidizing agents?
No, because they do not have a hydrogen on the carbon atom to which the -OH group is bonded. Results in "No reaction"
190
Properties of phenols
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
Phenols are usually names with what ending (instead of benzene)
-phenol. Eg. p-Chlorophenol
192
Many biomolecules contain a hydroxyl-substituted benzene ring
Draw tyrosine and eugenol
193
Acidity of alcohols and phenols
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
An alkoxide ion or anion of an alcohol is as strong a base as a hydroxide ion. How can alkoxide ions be produced?
By reacting an alcohol with a strong base or by reaction of an alkali metal with an alcohol
195
Acidity of alcohols and phenols
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
What is an ether?
Compounds with two organic groups bonded to the same oxygen atom.
197
How are ethers named?
By identifying the two organic groups and adding the word ether
198
Cyclic esters are often referred to by their common names
Epoxide (ethylene oxide)
Tetrahydrofuran
1,4-Dioxane
199
An -OH group is referred to as what
Alkoxy group
200
Draw dimethoxyethane
Draw
201
Describe an ether
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
Draw the structure for 3-methoxy-2-butanol
Draw
203
What do skunks repel with horrible odors as with garlic and onion, what is this caused by?
Thiols
204
Thiols describe
Also called mercaptans, compounds that contain an -SH group
205
What is added to make leak detection easy due to natural gas being odorless
Methanethiol
206
Thiols react with mild oxidizing agents to yield what?
Disulfides. Two thiols join in this reaction the hydrogen from each is lost, and a bond forms between the sulfurs
207
Where do thiols come from?
Amino acid cysteine which is part of many proteins
208
The proteins in hair are usually rich in S-S and S-H groups
Know
209
True or false. A permanent wave results when disulfide bridges are formed between -SH groups in hair protein.
True
210
What are the simplest halogen-containing compounds?
Alkyl halides, RX.. F Cl Br I
211
Draw methyl bromide
Draw
212
Draw ethyl bromide
Draw
213
Draw phenyl bromide
Draw
214
Describe aryl halides
Compounds that have an aromatic group bonded to a halogen atom, Ar - X
215
Describe stereochemistry
The study of the relative three-dimensional spatial arrangement of the atoms in a molecule
216
Stereochemistry
Mirror planes
217
What are stereoisomers
Isomers that have the same molecular and structural formulas but different spatial arrangements of their atoms
218
Can stereoisomers be converted into one another through rotation?
No.
219
How to remember stereoisomers
They have handedness. Cannot be placed directly on top as they won't align.
220
When does chirality occur
When an object lacks symmetry. Without a plane of symmetry is achiral
221
Chiral carbon atom
A carbon atom that is both tetrahedral and has four different groups attached to it
222
Enantiomers / optical isomers
The two mirror images forms a chiral molecule like 2-butanol
223
Are enantiomers a type of stereoisomer?
Yes
224
Properties of pairs of enantiomers
Have many of the same physical properties, same melting point, solubility in water, isoelectric point, and density
225
How do pairs of enantiomers differ?
In their biological activity, odors, and tastes, their effect on polarized light
226
One enantiomer will rotate one way, the other a different way. What are these?
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
Who is credited with the discovery of enantiomers?
Emil Fischer
228
Most importantly, how do pairs of enantiomers differ
As drugs
229
Practice determining which carbons may be chiral
Practice
230
A carbonyl compound is any compound that contains what
C = O - carbonyl group
231
What group does each of these belong to?
Acetaldehyde
Acetone
Acetic acid
Methyl acetate
Acetamide
Aldehyde
Ketone
Carboxylic acid
Ester
Amide
232
Why are carbonyl groups strongly polarized
Oxygen is more electronegative than carbon
233
What gives rise to the reactivity of the carbonyl group
The polarity
234
Bond angles between the three substituents on the carbonyl carbon atom
120°
235
Do aldehydes and ketones have similar or different properties?
Similar
236
Why do aldehydes and ketones have similar properties?
Because their carbonyl groups are bonded to carbon and hydrogen atoms that do not attract electrons strongly
237
What is an aldehyde?
A compound that has a carbonyl group bonded to at least one hydrogen, always ends in carbon chain
238
What is a ketone?
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
Draw the line structure for 1-phenylpropanone
Draw
240
Draw the line structure for 1-cyclohexyl-3,3-dimethyl-2-butanone
Draw
241
Are aldehydes and ketones polar or non-polar
Polar (moderately) - due to the presence of carbonyl group
242
Why do aldehydes and ketones have lower boiling points than alcohols but higher boiling points than alkanes
Dipole-dipole interactions
243
What are common aldehydes and ketones usually (gas, liquid, solid?)
Liquids
244
Many aromas and flavors derive largely from what?
Naturally occurring aldehydes and ketones
245
Formaldehyde properties
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
Properties of acetaldehyde
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
Properties of Acetone
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
Properties of Benzaldehyde
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
What is replaced during aldehyde oxidation
The hydrogen bonded to the carbonyl carbon is replaced by an -OH group
250
Do ketones react with oxidizing agents?
They do not have this hydrogen so they do not react cleanly.
251
Can aldehydes be reduced?
Yes to primary alcohols
252
Can ketones be reduced?
Yes to secondary alcohols
253
How do reductions occur - ketones and aldehydes
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
A -- ion has a lone pair of valence electrons. Both electrons are used to form a covalent bond to the carbonyl carbon
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
UP TO SLIDE 95
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
Aldehydes undergo addition reactions in which an alcohol combines with what?
The carbonyl carbon and oxygen
257
What is the additional product of additional reactions for alcohols?
Hemaicetals
258
What is a hemiacetal?
Have both an alcohol-like group - OH and an etherlike group -OR bonded to what was once the carbonyl carbon atom
259
How are hemiacetals formed?
From the carbonyl-group oxygen and the OR from the alcohol bonds to the carbonyl-group carbon
260
Differentiate hemiacetals and hemiketals
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
Can hemiacetals revert to aldehydes or ketones?
Yes! Through the loss of alcohol and establish an equilibrium with the aldehyde or ketone
262
Hemiacetal formation are they stable or not? whats the major exception?
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
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Acetal formation
Hemiacetals can react with a second alcohol molecule to form an acetal.
264
What is an acetal?
A compound that has two etherlike groups bonded to what was the carbonyl carbon atom
265
Acetal hydrolysis describe
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
What is acetal hydrolysis?
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
What is written above the arrow for acetyl hydrolysis?
Acid catalyst
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What does an amine contain?
One or more organic groups bonded to nitrogen
269
Amines
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
How to name primary alkyl amines
Named by identifying the alkyl group attached to nitrogen and adding the suffix- amine to the alkyl group name eg. ethylamine or isopropylamine
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Do simple secondary and tertiary amines have identical or different alkyl groups?
Identical
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What to do when the R groups in secondary or tertiary amines are different?
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
Draw the structure of N,N-diethylbutylamine
Draw
274
What is the -NH2 functional group?
Amino group
275
The simplest aromatic amine is known as what?
Aniline
276
What is responsible for many properties of amines?
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
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What causes amides to act as lewis bases
Nonbonding electron pair
278
What is a Lewis base?
A compound containing an unshared pair of electrons
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What type of amines can hydrogen bond with one another and with water?
Primary and secondary amines
280
Properties of amines (1° and 2°)
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
Amines with up to how many carbons have appreciable solubility in water due to hydrogen bonding?
6
282
What functional group is this associated with? Some volatile -- have strong odors. Some smell like ammonia and others like stale fish or decaying meat
Amines
283
What type of amines are irritating to the skin, eyes, mucous membranes and are toxic by ingestion?
Simpler amines
284
What types of amines are isolated from various plants and can be very poisonous?
Complex amines
285
Heterocycle describe
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
Why are aqueous solutions of amines weakly basic?
Because of the formation of -OH and R3NH+ ions in water
287
What happens when an amine is pronated?
It's electron pair will become positively charged (called ammonium ion)
288
What is the conjugate acid of an amine?
Ammonium ion, will form whenever an amine is in water or in the presence of an acid
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In a acidic aqueous solution, what is the acidic species?
H3O+. Hydronium will donate a proton to an amine forming an ammonium ion.
290
When amines act as bases, what do ammonium ions act as?
Weak acids
291
What happens with ammonium ions with bases?
The amine can be regenerated
292
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
True
293
What is an alkaloid?
A naturally occurring nitrogen-containing compound isolated from a plant or animal usually basic, bitter and poisonous
294
The bitterness and poisonous nature of this likely protects plants from being devoured by animals
Alkaloids
295
Describe atropine
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
Describe Ergotamine
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
How many alkaloids are present in the poppy?
20. Incl. morphine and codeine.
298
What type of compound contains a carbonyl group bonded to an electronegative heteroatom?
Type 2
299
Carboxylic acid describe
Have an -OH group bonded to the carbonyl group
300
Describe esters
Have an -OR group bonded to a carbonyl carbon (R - C=O (above not linear) - OR)
301
Abbv. for esters
- CO2R
302
What group do amides have bonded to the carbonyl carbon?
-NH2, -NHR OR -NR2(amino group)
303
How are amides classified?
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
Properties of carboxylic acids
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
C. acids features
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
C. acids undergo what type of reactions most commonly? explain
Carbonyl-group substitution reactions in which a group we represent as -Z relaces the group bonded to the carbonyl carbon atom.
307
Naming for c. acids
Normal rules. Identified by Greek letters though , a , b, y, and so on rather than numbers
308
Dicarboxylic acid describe
Contain two - COOH groups and are names systemically by adding the ending -dioic acid to the alkane name
309
Unsaturated acids are named with "-enoic" - different to saturated which is anoic
Enoic = double bond
Anoic = single bonds
(C = O disregarding this double bond)
310
Can esters be convertyed back to C. acids? if yes how
Yes. Through hydrolysis
311
Ethyl Ester boling point compared to acetic acid and methyl ester
Acetic = 118° C
Methyl ester = 57° C
Ethyl ester = 77° C
312
What do esters have that is different that they "contain" within their structures?
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
Example of ester naming ethyl acetate
The first part is acetic acid, second is ethyl alcohol
314
Amide description
Compounds with nitrogen directly attached to the carbonyl carbon atom are amides
315
What amides are soluble in both water and organic solvents?
Unsubstituted amides with low molecular weight
316
Describe hydrogen bonding for monosubstituted amides and disubstituted amides
Monosubstituted amides can also form hydrogen bonds to each other, disubstituted amides cannot do so and are therefore lower boiling
317
Difference between amides and amines
The nitrogen atom is bonded to a carbonyl group carbon in an amide but not an amine
318
In an amide, the nitrogen atom may have an alkyl substituent in it. How is this names?
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
The portion of the carboxylic acid that does not change during a carbonyl group substitution reaction is known as what?
Acyl group
320
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?
-oyl
321
Exception for acyl group from acetic acid is called what?
Acetyl group
322
What is a carboxylate anion?
The anion that results from the ionization of a carboxylic acid
323
What reaction do c.acids undergo?
Neutralization
324
C.acids undergo neutralization to form what?
Carboxylic acid salt and water
325
Describe esterification
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
How are amides formed?
By the acylation of amines. Acylation of an amine involves the replacement of the N-H bond with an acyl group.
327
Primary amide formation
A process where unsubstituted amides are formed by the reaction of c.acids with ammonia
328
Secondary amide formation
Secondary amides are formed by the reaction of a carboxylic acid and a primary amine
329
Tertiary amine formation
Tertiary amides are formed by reaction of carboxylic acid and a secondary amine
330
What happens when a tertiary amine reacts with a carboxylic acid?
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
What process do esters and amides undergo to give back c.acids plus alcohols or amines?
Esters and amines
332
Hydrolysis of esters
Substitution reaction
R - (C = O) - OR + H - OH --> R - (C = O) - OH + O - OR
333
Hydrolysis of amides
R - (C=O) - N - R (x2) + H - OH --> R - (C = O) - OH + H - N - R(x2)
334
What does acid-catalyzed hydrolysis do?
Reverse esterification
335
Ester hydrolysis using a base such as NaOH or KOH is known as what?
Saponification
336
Amide hydrolysis properties
Amides are stable in water, but hydrolyze with heating in the presence of acids or bases
337
Phosphate ester
A compound formed by the reaction of an alcohol with phosphoric acid
338
Possible diester and triesters
Dimethyl phosphate (phosphate diester) and trimethyl phosphate (phosphate triester)
339
Are phosphate monoesters diesters basic or acidic?
Acidic as they contain acidic hydrogen atoms. In neutral or alkaline solutions they are ions.
340
How is diphosphoric and triphosphoric acid formed?
By two or three molecules of phosphoric acid combine to lose water. The collective name is called anhydrides.
341
The PO3 2- group is part of a larger molecule known as what?
Phosphoryl group
342
What is the transfer of a phosphoryl group from one molecule to another called
Phosphorylation
343
In biochem, phosphoryl groups are provided by ATP which is converted to an ADP in a reaction accompanied by what?
The release of energy
344
Definition of biochemistry
The study of molecules and their reactions in living organisms
345
Where is the word protein from?
Greek language, means primary.
346
What is a protein?
A description for the biological molecules that are of primary importance to all living organisms
347
What roles do proteins play in living things?
Structural: They provide structure - keratin, actin throughout our bodies
Hormones: Signalling molecule/protein
Catalyst: Molecular machinery
Storage and transport
Immunity
348
Proteins are polymers of what?
Amino acids
349
What do all amino acids contain?
An amine group, a carbonyl group and an R group called a side chain bonded to a central carbon atom
350
How can amino acids be drawn?
Neutral form or in ionized form Zwitterion
351
How many amino acids are there
20
352
How many letters in an amino acid code
3
353
For how many of these amino acids has the only identity of the side chain attached to the carbon differing
19
354
What amino acid is a secondary amine whose nitrogen and carbon ring are joined in a 5 membered rin
Proline
355
Non-polar A.A
Glycine, alanine, valine, proline, leucine, isoleucine, methionine, tryptophan, and phenylalanine (all are hydrophobic)
356
Polar A.A
Serine, threonine, tyrosine, asparagine, glutamine, cysteine
357
A.A with positve charge
Lyesine, Arginine, Histidine
358
A.A with negative charge
Aspartic acid, glutamic acid
359
Forces present between amino acids are called what?
Intermolecular
360
Types of intermolecular forces present between amino acids or between proteins are called what?
H-bonding, London dispersion forces, Ionic bonding, Disulfide bonds
361
Non-polar side chains on amino acids are described as what
hydrophobic
362
What strategy is used to avoid aqueous fluids?
Nonpolar side chains gather into clusters to create a water-free environment
363
What regions in a protein are hydrophilic (water-loving)
The polar, acidic , and basic side chains
364
How many of the common amino acids are chiral?
19
365
What is the only achiral amino acid?
Glycine
366
Nature only selects what form of amino acids for making proteins?
L-amino acids
367
What is zwitterion
A neutral dipolar ion that has one positive charge and one negative charge
368
Amino acids contain two groups, what are they?
Acidic group - COOH and basic group - NH2. These two groups can undergo an intramolecular acid base reaction to form a zwitterion
369
Amino acids have the characteristics of what?
Salts
370
The zwitterion can either pronate or accept a proton depending on what?
The pH of the environment
371
In a basic environment, the ammonium will -- a proton to the base?
Donate
372
In an acidic environment the carboxylate will -- a proton from the acid
Accept
373
Isoelectric point (pI) describes what?
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
Is the pI for each amino acid different? if so why?
Yes, due to the influence of the side-chain
375
Why are side-chain interactions important? in amino acids
To stabilize a protein structure. It is important to be aware of charges at physiological pH.
376
What does the isoelectric point influence?
Protein solubility and determine which amino acids in an enzyme participate directly in enzymatic reactions
377
What is a peptide bond?
An amide bond that links two amino acids together
378
How does a dipeptide result?
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
Does the sequence of amino acids in a peptide or protein chain matter?
Yes, the exact sequence. Variation can indicate a different molecule. Ala-Ser is not the same as Ser-AlA
380
What is the peptide order rule
N -> C terminal amino acid
381
What is at the N - N-terminus?
The free - NH3+ group
382
What is at the C - Terminus?
The free -CO2H group on the right
383
Individual amino acids joined in the chain are referred to as what?
Residues
384
How is a peptide named?
By citing the amino acid residues in order, starting at the N-terminus and ending at the C-terminus
385
What is the primary structure
The sequence of amino acids in a protein chain
386
What is along the backbone of a protein?
A chain of alternating peptide bonds and a -carbon atoms
387
How do the carbon and nitrogen atoms along the backbone lie
In a zigzag arrangement with tetrahedral bonding around the a-carbon atoms
388
Primary protein structure 1st degree
Very crucial to function that the change of only one amino acid can drastically alter a protein's biological properties
389
What are the two hormones secreted by the pituitary gland differ in only two amino acids in the primary sequence?
Oxytocin, Vasopressin
390
What does vasopressin do?
Regulates blood pressure, blood osmolality, and blood volume
391
What does oxytocin do?
Known to stimulate uterine contractions in labor and childbirth to stimulate contractions of breast tissue to aid in lactation after child birth
392
Interactions between the backbone of amino acid residues induces changes to the shape of the primary structure. What does this refer to?
Secondary structure
393
What are the two kinds of repeating patterns in the secondary structure
Alpha helix and beta-sheet
394
Alpha helix
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
Beta-sheet
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
Proteins are classified in several ways which is to identify them as either -- or --
Fibrous proteins or globular proteins
397
Fibrous proteins
Tough, insoluble protein whose chains form fibers or sheets
398
Globular protein
Water soluble proteins whose chains are folded in a compact shape with certain types of groups on the outside
399
Tertiary proteins structure
The way in which an entire protein chain is coiled and folded into its specific three-dimensional shape.
400
There are four forces responsible for the tertiary structure of a protein
1. Hydrogen bonding
2. Salt bridges (ionic)
3. Hydrophobic interactions
4. Hydrophobic interactions
also disulfide linkages
401
Hydrogen bonding - proteins tertiary
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
Side chain - salt bridges in proteins tertiary
Where there are ionized acidic and basic side chains the attraction between their positive and negative charges creates salt bridges
403
Hydrophilic - proteins tertiary
Amino acids with charged R groups will interact with water through hydrogen bonding
404
Hydrophobic interactions - proteins tertiary
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
Covalent sulfur-sulfur bonds (disulfide bridge)
Cytestenine amino acid ress
