Organic Chemistry

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Organic Chemistry by Mind Map: Organic Chemistry

1. Alcohols Suffix = ol hydroxy

1.1. Different classifications based on where the OH is located

1.1.1. Primary alcohol The OH group is attached to a carbon that is all on its own

1.1.2. Secondary alcohol the OH group is attached to a carbon that is attached to 2 other carbons

1.1.3. Tertiary alcohol The OH group is attached to a carbon that is attached to 3 other carbons

1.2. Physical properties

1.2.1. OH group is polar

1.2.2. Solubility small alcohols are soluble due too HYDROGEN BONDNG

1.2.3. Boiling point higher boiling points then hydrocarbons do to the hydrogen bonding BP increases as the number of carbons increases BP decreases from primary to tertiary alcohols due to top steric hindrance

1.3. Functional group

1.3.1. Hydroxyl group OH

1.4. Chemical preperation

1.4.1. Hydration (oxidation) of alkenes make alcohols

1.4.2. Hydrogenation (reduction) of an aldehyde or ketone aldehydes will be reduced to primary alcohols ketones will be reduced to secondary alcohols through the addition of an H2

1.5. Chemical reactions

1.5.1. Combustion methanol and ethanol in race cars oxygenated gas

1.5.2. Oxidation Only primary and secondary alcohols undergo oxidation with mild oxidizing agents to form aldehydes and ketones because 2 hydrogen atoms are removed Aldehydes further oxidized to carboxylic acids

1.5.3. Dehydration (removal of water molecule) Intramolecular dehydration (elimination reaction) removal of water from a singe alcohol can be done to 1*,2* and 3*alcohols Zaitsev's rule applies to the intramolecular dehydration of 2* and 3* alcohol used to determine the major product because more then one alkene can be produces the adjacent carbon containing fewer H's will lose the H atom Intermolecular dehydration (condensation reaction) removal of water collectively from 2 alcohols to form an ether and water only occurs with primary alcohols

1.5.4. Halogenation halogen atom substituted for the OH group produces alkyl halide single product is formed using heat

1.5.5. Polymerization alcohol monomers repeatedly added together

2. need 180 degrees and an acid catalyst

3. Phenols OH is always carbon 1 phenol

3.1. functional group

3.1.1. hydroxyl group attached to a benzene ring

3.2. Physical proerties

3.2.1. solubility slightly soluble in water

3.2.2. state at room temperature solids or oily liquids

3.2.3. properties antiseptic: a substance that kills microorganisms on living tissue disinfectant is a substance that kills microorganisms on an inanimate objects

3.3. Chemical properties

3.3.1. flammible cannot be dehydrated

3.3.2. can be oxidyzed with strong oxidizing agengts weak acids in solution

3.4. Uses

3.4.1. 2% phenol is used as a surgical antiseptic

3.4.2. derivatives used as an antiseptic and a disenfectant

3.4.3. foods used as an antioxidant used as a peservatives

3.4.4. anaesthetic

4. Carboxylic Acids

5. Amines

6. Esters

7. New Node

8. Ethers oxy

8.1. oxygen single bonded to 2 carbons c-o-c

8.2. ethers are produced through intermolecular dehydration of primary alcohols

8.3. Uses

8.3.1. MTBE is a gasoline additive

8.3.2. diethyl ether is was ageneral anaesthetic

8.4. Isomerism

8.4.1. constitutional isomers due to different partitioning of R groups or functional groups isomers with alcohols

8.5. Physical properties of ethers

8.5.1. solubility more soluble in water than alkanes due to H-bonds with water similar solubility to alcohols

8.5.2. Boiling point similar to alkanes lower then alcohols

8.6. Chemical properties

8.6.1. flamible form explosives

8.6.2. unreactive with acids, bases, and oxidizing agents

8.6.3. good solvents due to there unreactivity easy to remove after areaction

8.7. Cyclic ethers

8.7.1. oxygen atom contained in carbon ring (o replaces a c in the ring)

8.8. Thiols

8.8.1. sulphur analog of alcohols because of the functional group R-SH

8.8.2. lower boiling points than alcohols NO hydrogen bonds

8.8.3. strong and bad odour

8.8.4. easily oxidized to form disulfides R-S-S-R important in protein structure (hair)

9. Aldehydes al

9.1. contain the carbonyl functional group C=O

9.1.1. polar bond with trigonal planar shape

9.2. have a carbonyl group at the end carbon ONLY

9.3. prepared by

9.3.1. oxidizing a primary alcohol with a mild oxidizing agent removes 2 H atoms to form C=O can be further oxidized to form a carboxilic acid by adding an oxygen atom thus aldehydes must be protected from the air if you do not want further oxidation to occur

9.4. Simple aldehydes

9.4.1. Methanal formed by oxidizing methenol an irritating gas carcinogenic to the skin used to preserve biological speciments

9.4.2. Benzaldehyde benzene ring attatched to methanal gives almonds their flavour

10. What they both have in common

10.1. physical properties

10.1.1. boiling points between alcohols and alkanes higher boiling points than alkanes because C=O is polar thus dipole dipole atrtactions between the carbonyl groups lower boiling points then alcohols because they can't H-bond between molecules

10.1.2. solubility aldehydes and ketones H-bond with water so low molecular mass compounds are soluble in water the longer the chain the less soluble or eventually insoluble they become

10.2. Uses

10.2.1. high molecular massed aldehydes and ketones have a pleasant smell and pleasant flavours

10.2.2. found widely in nature

10.3. Isomerism

10.3.1. Constitutionally isomerism, skeletal for both positional for ketones and functional groups subtypes

10.4. Chemical reactions

10.4.1. Oxidation only aldehydes will further oxidize Tollens test (silver mirror) AgNO3 added to an aldehyde soution positive test indicated by the oxidation of aldehyde to carboxylic acid and the reduction of Ag+ ions to silver metal, Ag example of a redox reaction, where Ag is the oxidizing agent Benedict's test (copper brick) solution of CuSO4 added to unknown solution if clear blue solution turns into a brick read suspension aldehydes were oxidized to carboxilic acids, the blue Cu2+ ions were reduced to red Cu+ ions example of a redox reaction where Cu2+ is the oxidizing agen originally used to detect glucose in the blood and urine to diagnose diabetes

10.4.2. Reduction can be reduced by adding hydrogen gas to reform primary and secondary alcohols

10.4.3. Hemiacital formation can be intermolecuar - to form a straight chain o rit can be an intramolecular reaction to form a cyclic hemiacital which are more stable caused by a reaction of an aldehyde or ketone with an alcohol the H atom of the alcohol is added to the O atom of the carbonyl group and or OR portion of the alcohol is added to the C atom of the carbonyl group in the presence of an acid catylist hemiacital is an alcohol group and ether group attached to the same carbon

10.4.4. Acetal formation reaction of a hemiacital with another alcohol molecule condensation reaction because there is a removal of water (still need an acid catalyst) more stable functional group is made up of 2 ether groups bonded to the same carbon

10.4.5. Polymerization under acidic conditions phenol and formaldehyde monomers react to form phenol-formaldehyde network polymers network polymers monomers connected in a 3D cross-linked network first man-made plastic was a phenol-formaldehyde polymer called makelite today used as adhesive for plywood

11. Ketones one

11.1. prepared

11.1.1. through oxidation of seconday alcohols with mild oxidizing agent to remove 2 hydrogen atoms to form C=O can not be further oxidized

11.2. contain the carbonyl functional group C=O and R-CO-R

11.2.1. polar bond with trigonal planar shape

11.2.2. carbonyl group is located in the carbon chain

11.3. Cyclic ketones exist

11.4. Ketone functional group has lower priority than an aldehyde when both are present the ketone is named as a substituent (oxo) (oxopentanal)

11.5. Uses

11.5.1. propanone (acetone simplest ketone formed by the oxidation of 2-propanol used as a solvent because it is soluble in both water and nonpolar subsances byproduct of fat breakdown component of nail polish remover

11.5.2. steroid hormones testosterone, progesterone,and cortisone

11.5.3. sunscreens and sun-tannng agents