Organic Chemistry 3 Flashcards
The branch of chemistry that deals with certain carbon containing compounds
Organic Chemistry
An organic compound that contains only carbon and hydrogen
Hydrocarbon
A chemical formula expressing the number of atoms of each element present in a molecule of a substance without indicating how they are linked
Molecular Formula
A chemical formula showing the spatial arrangement of the atoms and the linkage of every atom
Structural Formula
The possession by 2 or more distinct compounds of the same molecular formula, each molecule having the same # of atoms of each element but in a different arrangement
Isomerism ex: Glucose, Fructose, Galactose (C6H12O6)
A condensed version of the structural formula, written all on one line and demonstrating the relationship of the substituent groups in a molecule
Line Formula
Expression of the fixed ratio between carbon and hydrogen in hydrocarbons
Type Formula
Pertaining to any member of one of the two major groups of organic compounds, those having straight or branched chain structures
Aliphatic
A specific atom or group of atoms that is attached to a carbon atom in an organic compound & that imparts an identifiable chemical behavior to the compound
Functional Group
A formula that denotes a class of compounds and includes the functional group and a symbol R denoting a radical
General Formula
The existence of an element in 2 or more distinct forms ex: O, O2, O3
Allotropism
A hydrocarbon that contains only single bonds
Saturated Hydrocarbon
A saturated hydrocarbon that has only carbon-carbon single bonds Type Formula: CnH2n+2
Alkane
A monovalent radical formed when an alkane loses one hydrogen atom Type Formula: CnH2n+1
Alkyl Group
An aliphatic hydrocarbon with one or more halogen atoms attached. Gen. Formula: RX
Alkyl Halide
An organic compound that has one or more double or triple bonds between two carbon atoms
Unsaturated Hydrocarbon
An unsaturated hydrocarbon containing at least one carbon-carbon double bond Type Formula: CnH2n
Alkene
An unsaturated hydrocarbon containing at least one carbon-carbon triple bond Type Formula: CnH2n-2
Alkyne
Any compound containing a resonace-stabilized ring
Aromatic
Pertaining to ring compounds that contain one or more elements other than carbon in the ring
Heterocyclic Compounds
A large molecule made by linking together any number of monomers, or basic chemical units
Polymer
An organic compound containing one or more hydroxyl groups. Gen. Formula: ROH
Alcohol
An alcohol with only one hydroxyl group ex: Isopropanol, Tert-butanol
Monohydroxy Alcohol
An alcohol containing two hydroxyl groups ex:Ethylene Glycol
Dihydroxy Alcohol
An alcohol having three hydroxyl groups ex: Glycerol
Trihydroxy Alcohol
Those alcohols generally having more than three hydroxyl groups ex: Sorbitol
Polyhydroxyl Alcohol
An alcohol in which the hydroxyl group is attached to a carbon that is attached to no more than one other carbon ex: Methanol (Methyl Alcohol, Wood Alcohol) Ethanol (Ethyl Alcohol, Grain Alcohol)
Primary Alcohol
An alcohol in which the hydroxyl group is attached to a carbon that is attached to two other carbons ex: Isopropanol (Isopropyl Alcohol, Rubbing Alcohol)
Secondary Alcohol
An alcohol in which the hydroxyl group is attached to a carbon that is attached to three other carbons ex: Tert-butanol
Tertiary Alcohol
A chemical compound similar to alcohol in which the oxygen of the hydroxyl group is replaced by a sulfhydral group (-SH) Gen Formula: RSH
Thioalcohol/Mercaptan
Any organic compound with the gen. formula ROR’, where R & R’ are hydrocarbon groups formed by dehydration between two alcohols
Ether *Formed during the dehydration of an alcohol where sulfuric acid (H2SO4) is the dehydrating agent
An organic compound containing one or more -CHO groups formed by the oxidation of a primary alcohol Gen Formula: RCHO *-CHO is at the end of the chain
Aldehyde
Name some examples of aldehydes
*Methanal (Formaldehyde, HCHO) *Ethanal (Acetaldehyde) *Benzaldehyde (an aromatic)
An organic compound containing two aldehyde radicals ex: Glyoxal, Glutaraldehyde
Dialdehyde
Formaldehyde gas dissolved in water at 37% by weight and 40% by volume
Formalin
Any of a class of organic compounds containing the carbonyl group (C=O) whose carbon atom is joined to two other carbon atoms; the carbonyl group occurs within the carbon chain
Ketone ex: Propanone (Acetone)
How are ketones formed? What is their general formula?
*By the oxidation of a secondary alcohol *Gen Formula: RCOR
An organic compound containing the carboxyl group (-COOH) at the end of the carbon chain *Gen Formula: RCOOH
Carboxylic Acid ex: Methanoic Acid (Formic Acid) Ethanoic Acid (Acetic Acid, Vinegar)
A compound with the general formula RCOOR’ formed from an alcohol and organic acid by the removal of wather *Functional group is in the middle of the chain
Ester ex: Ethyl Acetate, Methyl Salicylate (Oil of Wintergreen)
An organic compound containing nitrogen; formed from ammonia by replacement of 1 or more hydrogen atoms by organic radicals Gen Formula: RNH2 *Organic Base, -NH2=Amino Group (functional group)
Amine ex: Methyl Amine
Any compound derived from ammonia by substitution of a carbonyl (C=O) for hydrogen or from an organic acid by replacing the -OH of the carboxyl with an amino group
Amide ex: Diethyl Formamide, Urea
Name the general formula for an amide. How are they formed?
*Gen Formula: RCONHR *Formed by the reaction of an organic acid with ammonia or with amines **Salts formed by a neutralization reaction *Have an amide bond btn. a carbonyl group and a nitrogen
Surface-active agents that are usually used for disinfection of skin, oral, and nasal cavities & instruments; germicidal ex: Benzyl Alkonium Chloride(Zephiran Chloride, Roccal)
Quaternary Ammonium Compounds
How are QUATS formed? Name the quaternary ammonium ion.
*Quaternary ammonium salts are formed by the action of tertiary amines with organic halides *[NR4+]
A compound of hydrogen, carbon, and oxygen that is an aldehyde or ketone derivative of a polyhydroxy alcohol
Carbohydrate
A sugar in which the functional groups are hydroxyl groups (-OH) and an aldehyde group (-CHO)
Aldose
A sugar whose functional groups are hydroxyl groups (-OH) and a ketone group (C=O)
Ketose
The simplest form of a carbohydrate consisting of a single sugar molecule **they CANNOT be hydrolyzed to a smaller carb. molecule
Monosaccharide
Name 3 Monosaccharides
Glucose, Fructose, Galactose *Molecular Formula: C6H12O6
What does the oxidation of monosaccharides produce?
Carbon Dioxide and Water
A carbohydrate formed by the linking of two monosaccharide units (also forms water in a dehydration synthesis reaction) *Hydrolysis yields monosaccharides
Disaccharide
Name 3 Disaccharides
Sucrose, Lactose, Maltose *Molecular Formula: C12H22O11
A polymer made by linking together a number of simple sugar molecules (3+) *Hydrolysis yields disaccharides, further hydrolysis yields monosaccharides
Polysaccharide
Name 3 Polysaccharides
Starch, Glycogen, Cellulose
A 5 carbon sugar molecule
Pentose
A 6 carbon sugar molecule
Hexose
An animal starch made by forming chains of alpha glucose molecules; storage form of glucose in the liver and muscle
Glycogen
A chemical reaction in which a substance is broken down by water
Hydrolysis
derivatives of hydrocarbons in which one or more of the hydrogen atoms has been replaced by a hydroxyl (-OH) functional group
alchols
wood alchohol
methanol
grain alcohol
ethanol
general formula for an alcohol
R-OH
an alcohol that contains an -OH functional group attached to a carbon that has one or no carbon atoms directly attached to it
primary alcohol
an alcohol in which the -OH is attached to a carbon atom having two other carbon atoms directly attached to it
secondary alcohol
an alcohol in which the -OH is attached to a carbon atom having three other carbon atoms attached to it
tertiary alcohol
is methanol a primary, secondary, or tertiary alcohol?
primary
is isopropyl alcohol a primary, secondary, or tertiary alcohol?
secondary
is tert-butanol a primary, secondary, or tertiary alcohol?
tertiary
alcohol with one one -OH group or hydroxyl group
monohydroxy alcohols
an alcohol containing two hydroxyl groups
dihydroxyl alcohols
dihydroxyl alcohols are also called
diols
an alcohol containing three hydroxyl groups
trihydroxyl alcohols
trihydroxyl alcohols are also called
triols
glycerol or glycerin are examples of monohydroxy, dihydroxyl, or trihyrdroxyl alcohols?
trihydroxyl alcohol
ethylene glycol is an example of monohydroxy, dihydroxyl, or trihydroxyl alcohols?
dihydroxyl alcohol
methanol, ethanol, propanol, and butanol are examples of monohydroxy, dihydroxyl, or trihydroxyl alcohols?
monohydroxy alcohols
alcohols having more than one hydroxyl group (generally more than three)
polyhydroxy alcohols
sorbitol is an example of a ______ alcohol
polyhydroxy
an aromatic derivative of benzene with a hydroxyl group attached to it
phenol
weak acid
phenol
hydroxybenzene
phenol
any organic chemical that contains the -SH radical, formed when the oxygen of an alcohol is replaced by sulfur
mercaptan
what is the general formula for a mercaptan?
R-SH
mercaptans are also called
thiols
formed during the dehydration of an alcohol where sulfuric acid is considered a dehydrating agent that removes water from two molecules of alcohol
ether
the general formula for an ether
ROR
General Formula for Aldehydes
RCHO
General Formula for Ketones
RCOR
General Formula for Carboxylic Acids
RCOOH
General Formula for Esters
RCOOR’
What is the functional group in an Aldehyde and where is it located?
One or more CARBONYL groups (-CHO) are located at the END of the carbon chain.
What is the functional group in a Ketone and where is it located?
The CARBONYL group (C=O) is located in the WITHIN of the carbon chain-NOT at the end.
What is the functional group in a Carboxylic Acid?
The CARBOXYL group (-COOH)
Esters are produced by the reaction of an _____?______ with an _____?_____.
Esters are produced by the reaction of an ORGANIC ACID with an ALCOHOL. ex: RCOOH(carboxylic acid)+ ROH(alcohol)= RCOOR’(ester)+ water (water removed=dehydration)
What is an organic compound containing two aldehyde (-CHO) radicals called?
A Dialdehyde
Name three examples of Aldehydes.
- Methanal (formaldehyde; HCHO) 2. Ethanal (acetaldehyde) 3. Benzaldehyde
Aldehydes are formed by the ______?______ of _______?________.
Aldehydes are formed by the OXIDATION of A PRIMARY ALCOHOL.
How do we name Aldehydes?
- Start w/the parent hydrocarbon -e (Methane-e=Methan) 2. Add -al (Methan+al=Methanal)
Name two examples of Dialdehydes.
- Glyoxal (simplest. 2 carbonyl groups bonded together) 2. Glutaraldehyde (excellent germicide; Cold/Liquid sterilizing agent)
What is Formalin?
Formaldehyde gas dissolved in water at 37% by weight and 40% by volume.
What does HCHO form when it polymerizes?
Paraformaldehyde or solid formaldehyde. METHANOL slows polymerization. Polymerization occurs when a bottle of arterial is exposed to cold temps, has expired shelf life, the pH is less than 6.5, etc. Shouldn’t embalm with this!
Name an example of a Ketone.
Propanone (acetone; dimethyl ketone). Dissolves sticky stuff on skin or fingernails.
Ketones are formed by the ______?_______ of a _____________?____________.
Ketones are formed by the OXIDATION of a SECONDARY ALCOHOL.
How do we name Ketones with two different radical (R) groups?
Ketone general formula = RCOR. Put them in alphabetical order and put “Ketone” on the end. Ex: Ethyl group (R) + C=O + Methyl group (R) would be named ethylmethylketone.
Of Aldehydes, Ketones, Carboxylic Acids and Ethers, which 2 are neutralization products in an arterial fluid?
Carboxylic Acids & Esters.
Give three examples of salts used in arterial solutions that act as anticoagulants/sequestering/chelating agents for the calcium in hard water.
- Oxylates 2. Citrates 3. EDTA (ethylenediaminetetrasodiumacetate)
Give two examples of Carboxylic Acids.
- Methanoic Acid (formic acid) 2. Ethanoic acid (acetic acid; vinegar)
Explain the process of how an Alkane oxidizes to become a Carboxylic Acid.
An Alkane oxidizes to become an Alcohol, which oxidizes to become an Aldehyde, which oxidizes to become a Carboxylic Acid. ex: Methane–O2–>Methanol–O2–>Methanal–O2–> Methanoic Acid.
Explain the processof how a reduction reaction can turn a Carboxylic Acid into an Alkane.
A Carboxylic Acid reduces to an Aldehyde, which reduces to an Alcohol, which reduces to an Alkane. ex. Ethanoic Acid or Acetic Acid –>Ethanal–>Ethanol–>Ethane
An Ester is formed from an ____?____ and _______?________ by the removal of _____?_____.
An Ester is formed from an ALCOHOL and ORGANIC (CARBOXYLIC) ACID by the removal of WATER.
Give two examples of Esters.
- Ethyl acetate 2. Methyl salicylate (oil of wintergreen)
What do Esters usually end in?
They usually end in -ate or -oate
What is an Alkane?
An Alkane is a Saturated Hydrocarbon with only C-C and C-H Single bonds.
What is the general Formula for an Alkane?
CnH(2n+2)
Describe and explain the change in Boiling/Melting points of Alkanes:
As chain length increases, the boiling point increases as larger molecules have greater van der Waals forces between them. More Branching reduces the Melting points as the molecules cannot pack together well, reducing van der Waals forces.
Describe and explain the solubility of Alkanes in Water:
Alkanes are Insoluble in water because they are Non-Polar molecules and Water is only an effective solvent for Polar molecules.
Describe the reactivity of Alkanes:
They will burn in oxygen to produce CO2 and Water and they will react with Halogens under specific circumstances. Otherwise they are unreactive.
What is different between Fractional Distillation and normal distillation?
Fractional Distillation produces many different parts (or fractions) each with different boiling points, Distillation only separates the volatile and nonvolatile products.
Cracking:
Cracking is the process of breaking a long Hydrocarbon chain into shorter Hydrocarbon chains, some of which can be Alkenes.
Why is cracking useful:
Typically, the shorter Hydrocarbon chains are more economically desirable because they are more volatile, less viscous and have lower boiling points.
Name the two types of Cracking:
Thermal Cracking and Catalytic Cracking.
Thermal Cracking:
Is the process of breaking a Hydrocarbon chain under very high temp and very high pressure. When the chain is broken, each carbon gains an electron from the covalent bond, forming Free Radicals then forming Alkanes and Alkenes (useful for polymers).
Name the conditions required for Thermal Cracking:
Temp of 700K-1200K and Pressure of up to 7000kPa.
Name the two products from Thermal Cracking:
Alkanes and high percentage of Alkenes.
Outline the stages of the reaction involving the Hydrocarbon Chain in thermal Cracking:
Long Hydrocarbon chain —> Free Radical Intermediates —> Alkanes + Alkenes.
Catalytic Cracking:
Takes place at lower temp (700K) and lower pressure and uses a ZEOLITE catalyst. Products are mostly Motor fuels, Aromatic compounds, cycloalkanes and Branched Alkanes.
What are the main products of Catalytic Cracking:
Motor Fuels, Aromatic Compounds, Branched Alkanes and Cycloalkanes.
What are the conditions required for Catalytic Cracking:
High temps (720k) but lower than Thermal Cracking, relatively low pressure and the presence of a ZEOLITE catalyst.
What are the main economic reasons for Cracking long hydrocarbon chains:
To produce shorter hydrocarbon chains that are more valuable, eg Motor Fuels, Aromatic compounds and Alkenes for Polymers.
What are the use of Alkenes produced from Thermal Cracking?
To make Polymers, e.g. Ethene –> Polyethene.
What are the two types of Combustion of Alkanes:
Complete (in excess Oxygen) and incomplete (in limited or very limited Oxygen).
Write the products of Complete Combustion:
H2O and CO2.
Write the two different lots of products formed from incomplete combustion:
H2O and CO (Limited Oxygen) and H2O and C (Soot).
List the pollutants produced by burning Alkanes:
CO, CO2, NO(x), SO2, H2O, Unburnt Hydrocarbons.
Name the Greenhouse Gases produced from Burning Alkanes:
Carbon Dioxide, Water Vapour, Unburnt Hydrocarbons.
Name the compounds that contribute to Acid Rain:
Nitric Acid and Sulfuric Acid. (formed from NOx and SO2).
How can the Sulfur containing impurities be dealt with? (Flue Gases).
Calcium Carbonate Scrubbers or Calcium Oxide in Flues to make Gypsum (CaSO4).
How are Nitrogen Oxides formed?
From large heat causing the Oxygen in the air and Nitrogen to bond.
How can Carbon Monoxide and Nitrogen Oxide be dealt with?
Catalytic Converters, these honeycomb structures that are layered with Platinum create a large surface area and allow for the NO and CO to react together to produce N2 and CO2.
How can the Unburnt Hydrocarbons that are produced from burning Alkanes be dealt with?
The Catalytic Converter will allow for the Hydrocarbon and Nitrogen Oxide to react together to form N2, CO2 and H2O.
What is a special name given to the products: CO2, Unburnt Hydrocarbons (Methane etc) and H2O?
These are called greenhouse gases and they contribute to the greenhouse effect which can increase the rate of Global Warming.
What is an alcohol?
An organic compound that contains the hydroxyl group (-OH).
What do ethers contain?
Two alkyl groups bonded to an oxygen atom. They have no O-H hydrogens, so they can’t hydrogen bond with themselves.
What is the carbonyl group?
A carbon double-bonded to an oxygen.
What do ketones contain?
Two alkyl groups bonded to the carbonyl group.
What do aldehydes contain?
One alkyl group and a hydrogen atom bonded to the carbonyl group.
What is a main difference between nomenclature of aldehydes and ketones?
Ketones generally have the -one suffix, and aldehydes have either the -al or the -aldehyde suffix.
What do carboxylic acids contain?
The carboxyl group, or -COOH.
What is the carboxyl group composed of?
A carbonyl group and a hydroxyl group.
What is the systematic naming convention for carboxylic acids?
The “-oic acid” suffix.
What are the carboxylic acid derivatives?
Acid chlorides, esters and amides.
What is an acid chloride?
A carboxylic acid derivative where Cl is in place of the hydroxyl group bonded to the carbonyl group.
What is an ester?
A carboxylic acid derivative where an alkyl group replaces the acid proton in the hydroxyl group.
What is an amine?
An alkylated derivative of ammonia.
What is an amide?
A carboxylic acid derivative that has ammonia or an amine in place of the hydroxyl group.
Describe how hydrogen bonding can occur with amides.
One of the hydrogens from the highly polarized N-H bond will bond with the carbonyl oxygen that carries a partial negative charge as a result of resonance polarization.
What does a nitrile contain?
The cyano group, or -C(triblebond)N.
What are the two types of isomers?
Constitutional isomers and stereoisomers.
What is another name for constitutional isomers?
Structural isomers.
What is the difference between constitutional and stereoisomers?
Constitutional isomers have atoms connected to different atoms, and stereoisomers are connected to the same atoms, just oriented differently in space.
What Shape is Benzene:
It is a Planar molecule.
Why is Benzene more stable than theoretical alternate single and double bonds?
Because it has a Delocalised system of P electrons above and below the ring structure, essentially giving each c-c bond 3 electrons. Making it slightly between a Single and a Double bond.
What is the bond length in benzene Carbon bonds?
It is an intermediate of the C-C bond which is longer (154pm) and C=C (135pm) of 140pm. This is because of the delocalised electrons present.
Why does Benzene undergo Electrophilic Substitution rather than addition?
Because the loss of a H+ ion from the Carbocation formed by adding a group to bezene will restore its Aromatic properties by recreating the Cyclic Pi-System of electrons.
Name two reactions that occur with Benzene required:
Nitration (by Nitronium or Nitryl Ion) of Benzene and Fidel Crafts acylation.
Give the conditions, name the mechanism for and uses of the products from the Nitration of Bezene:
Conc H2SO4 and HNO3 acids are present to prepare the electrophile, done at under 50degrees C to prevent further substitution of NO2 groups. Electrophilic Substituition. Uses are to form TNT, and Amines.
Give the conditions, name the mechanism for and uses of the products from the Acylation of Benzene:
Undergoes Electrophilic Substitution. Done with AlCl3 Catalyst and products formed are useful in creating other substituted Aromatic compounds.
Why is the Hydrogenation of Bezene less exothermic than expected if it was alternate double bonding?
Because the stability of benzene comes from the delocalised Pi System of eletrons, this causes increased stability, thus less energy can be lost when hydrogenated.
Inorganic Compounds
Generally defined as compounds that lack carbon (except CO2 and CO)
Organic Compounds
Generally distinguished by the fact that they contain carbon
Three facts about organic compounds/compounds that contain carbon?
-Carbon chains are the backbone for many substances in living cells. -Each compound can be expressly suited for a particular function or structure -There are four major groups of organic compounds
What are the four major groups of organic compounds?
1)Carbohydrates 2)Lipids 3)Proteins 4)Nucleic Acids
3 Facts about Carbohydrates?
-Hydrophilic -a source of energy that can be quickly mobilized -less than 3% of our body weight
What are monosaccharides?
the simplest carbohydrates
Name the 3 monosaccharides
1)glucose (blood sugar) 2) fructose (fruit sugar) 3)galactose
What do monosaccharides and disaccharides have in common?
they are both “simple sugars” they are both sweet.
Isomers
Compounds with the same formula but a different arrangement of atoms in the molecule.
What is the formula for all monosaccharides?
C6H12O6
Disaccharides
sugars composed of two monosaccharides
What are the 3 Disaccharides?
1)Sucrose (cane sugar) 2)Lactose (milk sugar) 3)Maltose (found in germinating wheat)
Polysaccharides
10 to hundreds of monosaccharides joined together in a straight or branched chain
What do Glycogen, Starch and Cellulose have in common? (besides being polysaccharides)
They are not sweet and they are all composed solely of glucose
Glycogen
Energy-storage polysaccharide that animals manufacture and store
What is glycogen composed of?
Composed of many glucose molecules joined together in a chain
Where is glycogen manufactured and stored?
in the liver & muscle
How is glycogen produced and why?
After meals (when blood glucose is high), liver cells produce glycogen, so that in between meals it can break glycogen down and draw from it to maintain blood sugar levels
Starch
energy-storage polysaccharide that plants manufacture and store
How is starch produced and why?
when sunlight and nutrients are readily available, plant cells produce starch, so that it can draw from it when photosynthesis is not possible (i.e. at night, winter)
Example of starch; significance to human diet
potatoes; starch is the only significant digestible polysaccharide in the human diet
Cellulose
a structural polysaccharide that gives strength to cell walls of plants
Three facts about cellulose?
1)principal component of wood, cotton & paper 2) we can not digest it 3) the most abundant organic compound on earth.
Besides being a source of energy (carbohydrates digested to glucose, which is oxidized to ATP), carbohydrates have OTHER functions as well….
Carbohydrates are often conjugated with (covalently bound to) proteins & lipids
Glycolipids
lipids with a carbohydrate attached. found on the external surface of a cell
Glycoproteins
Proteins with a carbohydrate attached. Major component of mucus.
Proteoglycans
1)Macromolecules that form gels that help hold cells and tissues together 2)lubricate joints 3) Account for the tough rubbery texture of cartilage
Lipids: 5 facts?
-form essential structural components of all cells -hydrophobic -variable in structure -more calories per gram than carbohydrates -10-12% of our body weight
Triglycerides
“neutral fats” 3 fatty acids bound to a glycerol by dehydration synthesis.
Draw a triglyceride?
just draw the glycerol as a rectangle with three fatty acids coming off (looks like the letter E)
2 Facts about triglycerides?
-found in adipose (fat) cells; (provide thermal insulation & shock absorption for vital organs) -most plentiful lipids in the body
Phospholipids
“modified triglycerides” instead of one fatty acid they have a phosphate group which is linked to other functional groups.
Draw a phospholipid?
don’t forget polar/hydrophilic head with two nonpolar/hydrophobic tails
2 facts about phospholipids?
-used to make up the cell membrane -have a polar & nonpolar end (hydrophilic and hydrophobic end)
Steroids
Ringed lipids
Cholesterol
The most important molecule in our steroid chemistry. It is the “parent” steroid from which the other steroids are made.
Where does cholesterol come from?
only 15% of cholesterol comes from the diet, the other 85% is internally synthesized.
is cholesterol bad for us?
Cholesterol is a natural product of the body and is necessary for human health. It is an important component of cell membranes and is required for proper nervous system function
What are the Fat Soluble vitamins?
They are essential for many normal functions. A, D, E, K
Vitamin A
eye function
Vitamin D
promotes uptake of calcium in the small intestine
Vitamin E
wound healing
Vitamin K
synthesis of proteins responsible for blood clotting
Proteins
Amino acids held together by peptide bonds
How many amino acids are there?
There are 20 different amino acids (half we eat = “essential”, the rest we manufacture)
protein chains?
-Some proteins are just a few amino acids long (i.e. hormones), others are very long chains
How proteins are integrated in body
-most abundant organic components of the human body -roughly 100,000 different types of proteins -much more complex in structure and function than carbohydrates or lipids -20% of our body weight
Structural role of proteins
Proteins are cellular building blocks
Physiological role of proteins
1)enzymes = “biological catalysts” that speed up reactions in the body 2)Hormones = “chemical regulators” secreted into the bloodstream that change or regulate the body 3)Antibodies = related specifically to immunity
Shape of enzymes
Enzymes have to be a very specific shape (that can only be achieved through hydrogen bonding combined with a very specific amino acid sequence).
“lock & key”
In almost every case, the function of a protein or enzyme depends on its ability to recognize and bind to some other molecule. EX: the enzyme (key) Sucrase can only fit with/”act” on the substrate Sucrose (Lactase breaks down Lactose, Maltase & Maltose
Nucleic Acids
polymers of nucleotides
Nucleotides
Organic compounds with three principal components: 1)Nitrogenous base 2)a 5-carbon sugar 3)one or more phosphate groups
What do nucleotides make up?
Nucleotides make up DNA & RNA. DNA is the largest of the nucleic acids: it is double helix structure of nucleotide chains held together by hydrogen bonds.
the only polysaccharide synthesized in the human body is_____
glycogen
the arrangement of a polypeptide into a fibrous or globular shape is called its
quaternary structure
which of the following functions is more characteristic of carbohydrates than of protein: -contraction -energy storage -catalyzing reactions -immune defense -intercellular comunication
energy storage
dietary antioxidants are important because they neutralize _____
free radicals
any substance that increases the rate of a reaction without being consumed by it is a/an _____. In the human body, _______ serve this function
catalyst, enzymes
the suffix ___ denotes a sugar, while the suffix ____ denotes an enzyme
-ose, -ase
the amphiphilic lipids of cell membranes are called ____
phospholipids
a substance acted upon and changed by an enzyme is called the enzyme’s ____
substrate
a-
not
aero-
oxygen (aerobic)
amphi-
both (amphiphilic)
caloro-
heat (calorie)
collo-
glue (colloid)
hydro-
water (hydrolysis)
-mer
part (polymer)
mono-
one (monomer)
oligo-
few (oligosaccharide)
-philic
loving (hydrophilic)
Hydroxide ion removes a proton from alpha-Carbon of the keto tautomer, forming enolate ion. Enolate ion has two resonance contributors. Protonation on oxygen forms enol tautomer, but protonation on alpha-carbon yields keto tautomer.
Base-Catalyzed Keto-Enol Interconversion
The acid protonates the carbonyl oxygen of keto tautomer. Water removes a proton from the alpha-carbon, forming the enol tautomer.
Acid-Catalyzed Keto-Enol Conversion
A base removes a proton from the alpha-carbon, forming an enolate in. The enolate ion reacts with an electrophile.
Base-Catalyzed Alpha-Substitution
The acid protonates the oxygen, the most electron-dense atom in the molecule. Water removes a proton from the alpha-carbon. The enol reacts with an electrophile.
Acid-Catalyzed Alpha-Substitution
The carbonyl oxygen is protonated. Water removes a proton from the alpha-carbon, forming an enol. The enol reacts with an electrophilic halogen. The very acidic protonated carbonyl group loses a proton.
Acid-Catalyzed Halogenation
The hydroxide ion removes a proton from the alpha-carbon, forming an enolate ion. The enolate ion reacts with the electrophilic halogen.
Base-Promoted Halogenation
All of the hydrogens of the methyl group are replaced by halogens. The product is a trihalo-substituted ketone. Hydroxide ion attacks carbonyl carbon of trihalo-substituted ketone. Transfer of a proton forms carboxylate ion and iodoform.
Haloform Reaction
PBr3 converts the carboxylic acid into an acyl bromide. The acyl bromide is in equilibrium with its enol. Bromination of the enol forms the alpha-brominated acyl bromide, which is hydrolyzed to the alpha-brominated carboxylic acid
Hell-Volhard-Zelinski Reaction
A base removes a proton from the alpha-carbon of the carbon acid. The enolate ion adds to the beta-carbon of an alpha,beta-unsaturated carbonyl compound. The alpha-carbon is protonated.
Michael Reaction
A base removes a proton from the alpha-carbon, creating an enolate ion. The enolate ion adds to the carbonyl carbon of a second molecule of the carbonyl compound. The negatively charged oxygen is protonated.
Aldol Addition
A base removes a proton from the alpha-carbon, forming an enolate ion. The enolate ion eliminates the OH group, which picks up a proton as it leaves to make it a better leaving group.
E1cB reaction
A base removes a proton from alpha-carbon, creating an enolate ion. The enolate ion adds to the carbonyl carbon of a second molecule of the carbonyl compound. The pi bond reforms, eliminating an alkoxide ion.
Claisen Condensation
A base removes a proton from the alpha-carbon, creating an enolate ion. The enolate ion adds to a carbonyl carbon. The pi bond reforms, eliminating an alkoxide ion.
Dieckmann Condensation
The first stage is a Michael reaction that forms a 1,5-diketone. The second stage is intramolecular aldol addition. Heating the basic solution dehydrates the alcohol.
Robinson Annulation
A proton is easily removed from alpha-carbon because it’s flanked by 2 ester groups. Resulting alpha-carbanion reacts with alkyl halide, forming alpha-substituted malonic ester.
Malonic Ester Synthesis
Heating alpha-substituted malonic ester in acidic aqueous solution hydrolyzes both ester groups to carboxylic acid groups, forming alpha-substituted malonic acid. Further heating decarboxylates 3-oxocarboxylic acid
Decarboxylating carboxylic acids
The alcohol displaces the chloride ion from the dimethylchlorosulfonium ion in an Sn2 reaction. The product of the first step loses a proton. An E2 reaction forms the aldehyde (or the ketone).
Swern Oxidation
The ketone and the peroxyacid form an unstable tetrahedral intermediate with a weak O-O bond. As the O-O bond breaks heterolytically, one of the alkyl groups migrates to oxygen. Similar to 1,2-shifts
Baeyer-Villiger Oxidation
OsO4 forms a cylic intermediate when it reacts with an alkene. Its a syn addition because both oxygens are delivered to same side of double bond. Intermediate is hydrolyzed with aqueous hydrogen peroxide. H2O2 reoxidizes reagent back to OsO4
Cis-Glycol Formation
An elecrophile adds to one of the sp2 carbons and nucleophile adds to the other. E+ at oxygen at one end of ozone w/ nucleophile at other end. Molozonide product is unstable due to two O-O bonds, immediately rearranges to more stable ozonide
Ozonide Formation
what are alkANES?
SATURATED hydrocarbons, general formula = Cn H2n+2
How many bonds can carbon atoms form?
4 (maximum)
what are cycloalkanes?
ring of carbon atoms general formula= CnH2n
What are structural isomers?
different arrangements of the same atom
What structural isomers can alkanes form?
Chain isomers, only when c-c bonds are switched (onto another carbon atom in the chain) is it an isomer. It is the SAME arrangement if it is rotated!
What do alkanes burn in?
Oxygen
What happens when alkanes form halogenoalkanes?
FREE RADICAL SUBSTITUTION.
What is free radical substitution?
Halogens reacting with alkanes, it can only be started by UV LIGHT.
What are the steps of free radical substitution?
1)initiation reaction- free radicals produced 2) propagation reactions- free radicals used up- in chain reactions 3)Termination reactions-free radicals form stable molecules
What is crude oil?
A mixture of hydrocarbons
What is petroleum?
crude oil, made mostly of alkanes.
How do you separate crude oil?
Fractional distillation
What are the steps of fractional distillation?
1) vaporised at 350c 2)fractionating column- largest dont vaporise turn into residual. 3)vapor goes up- is cooled, and condenses, therefore drawn off. 4) lowest boiling points don’t condense- turn into gases
What happens to the products in fractional distillation?
light fractions are more valuable-higher demand so are stored/sold. Heavy fractions are cracked.
What is cracking?
Breaking long chained alkanes into smaller hydrocarbons.
What are the conditions for thermal cracking?
high temp, high pressure. AlkENES are cracked using this method, form POLYMERS.
What are the conditions for catalytic cracking?
form motor fuels. aromatic, ZEOLITE catalyst, slight pressure, high temp
What can alkanes be reformed into?
cycloalkanes and aromatic hydrocarbons
what are uses of alkane fuels?
methane- used in cooking, central heating -petrol -jet fuel -diesel
what is the disadvantage of using alkanes?
are expensive, non-renewable, run out, PRODUCE EMISSIONS.
What emissions are produced from alkanes?
sulfur dioxides- scrubbers used to reduce output. Are poisonous. Produce acid rain- sulfuric acid. Carbon monoxide- formed by incomplete combustion, is a poisonous gas. Nitrogen oxide- forms acid rain, causes breathing problems- affects ozone layer.
What are greenhouse gases?
Formed from alkanes, absorb infrared leading to global warming.
AlkENES are?
UNSATURATED hydrocarbons. Formula= CnH2n
Alkene properties?
Are more reactive, have a double bond consisting of a pi and sigma bond. The double bond has a high electron density.
Adding hydrogen to c=c bonds produces?
AlkANES via ELECTROPHILIC ADDITION
What are the conditions for electrophilic addition?
nickel catalyst at 150c.
What happens in electrophilic addition?
Double bond opens- the pi bond is an electron rich area (is nucleophilic), which attracts the electrophile (hydrogen) meaning the hydrogen attaches itself to each of the carbons.
What is an electrophile?
Are electron pair acceptors, they are short of electrons, therefore are attracted to electron rich areas. Examples- Positively charged ions- H+ -Polar molecules
What is an nucleophile (electron rich area)?
A area high in electrons which is attracted to places which don’t have enough electrons. The double bond in C=C is nucleophilic.
What is a hazard?
anything that can cause harm
What is a risk?
chance of what you are doing can cause harm
what is a risk assessment?
is created to reduce risks, -working in a smaller scale -appropriate precautions, e.g. wearing eye protection -safer chemicals- lower concentration THIS MINIMISES RISK.
Hydrogen halides form (with a unsymmetrical alkene)?
2 products, mostly form the most stable carbocation!
Alkenes do what when they react with halogens and hydrogen halides?
ELECTROPHILIC ADDITION.
In order of stability, what are the most stable carbocations?
tertiary, secondary, primary.
What is the two tests for an alkene?
bromine water- turns colourless with alkenes, because the c=c bonds undergo electrophilic addition with bromine water. Alkenes are oxidised in acidified potassium manganate. turns from purple- to colourless.
E/z Isomerism?
Double bonds cant rotate, therefore carbons all lie on the same plane (are trigonal planar). Therefore their structural isomers are the same atoms but different arrangement- steroisomerism.
E isomerism
Is an isomer with DIAGONAL rotation. When the same groups are diagonally across the double bond.
What is stereoisomerism?
Are atoms with the same structural formula but different arrangement. Because of the lack of rotation, some alkenes have stereoisomers.
Z isomerism?
Is an isomer with VERTICAL AND HORIZONTAL rotation. When the same groups are vertically or horizontally across the double bond.
Cis isomerism?
Z isomer. This only applies if they have the same groups attached to them.
Trans isomerism?
REMEMBER ‘trane’ is a E isomer. This only applies if they have the same groups attached to them.
Alkenes can join to form?
additional polymers
What happens to the double bond in additional polymers?
The double bonds open up to form a long chain- a monomer (a repeated unit) forms lots of polymers!
What do polymers form?
Plastics (mostly)
What happens to waste polymer plastics?
waste plastics, can either be buried, recycled, or burned.
What is the problems with burying plastics?
they are unreactive, and non-biodegradable, meaning they lead to environmental damage.
What happens in the process of recycling?
plastics are sorted, them melted molded/remodeled down to make new plastics.
What is the problems of burning plastics?
heat is used, wasting electricity, toxic gases can be released (are prevented using a scrubber to neutralize)
Properties of biodegradable polymers?
decompose under right conditions. Are made from starch. Renewable materials- oil fractions.
What are the problems with biodegradable polymers?
you have to collect and separate them from other plastics. Are more expensive
