Organic Chemistry

Get Started. It's Free
or sign up with your email address
Rocket clouds
Organic Chemistry by Mind Map: Organic Chemistry

1. New Node

2. Alcohols Suffix = ol hydroxy

2.1. Different classifications based on where the OH is located

2.1.1. Primary alcohol

2.1.1.1. The OH group is attached to a carbon that is all on its own

2.1.2. Secondary alcohol

2.1.2.1. the OH group is attached to a carbon that is attached to 2 other carbons

2.1.3. Tertiary alcohol

2.1.3.1. The OH group is attached to a carbon that is attached to 3 other carbons

2.2. Physical properties

2.2.1. OH group is polar

2.2.2. Solubility

2.2.2.1. small alcohols are soluble due too HYDROGEN BONDNG

2.2.3. Boiling point

2.2.3.1. higher boiling points then hydrocarbons do to the hydrogen bonding

2.2.3.1.1. BP increases as the number of carbons increases

2.2.3.1.2. BP decreases from primary to tertiary alcohols due to top steric hindrance

2.3. Functional group

2.3.1. Hydroxyl group OH

2.4. Chemical preperation

2.4.1. Hydration (oxidation) of alkenes make alcohols

2.4.2. Hydrogenation (reduction) of an aldehyde or ketone

2.4.2.1. aldehydes will be reduced to primary alcohols

2.4.2.2. ketones will be reduced to secondary alcohols through the addition of an H2

2.5. Chemical reactions

2.5.1. Combustion

2.5.1.1. methanol and ethanol in race cars

2.5.1.2. oxygenated gas

2.5.2. Oxidation

2.5.2.1. Only primary and secondary alcohols undergo oxidation with mild oxidizing agents

2.5.2.1.1. to form aldehydes and ketones because 2 hydrogen atoms are removed

2.5.2.1.2. Aldehydes further oxidized to carboxylic acids

2.5.3. Dehydration (removal of water molecule)

2.5.3.1. Intramolecular dehydration (elimination reaction)

2.5.3.1.1. removal of water from a singe alcohol

2.5.3.1.2. can be done to 1*,2* and 3*alcohols

2.5.3.2. Zaitsev's rule

2.5.3.2.1. applies to the intramolecular dehydration of 2* and 3* alcohol

2.5.3.2.2. used to determine the major product because more then one alkene can be produces

2.5.3.2.3. the adjacent carbon containing fewer H's will lose the H atom

2.5.3.3. Intermolecular dehydration (condensation reaction)

2.5.3.3.1. removal of water collectively from 2 alcohols to form an ether and water

2.5.3.3.2. only occurs with primary alcohols

2.5.4. Halogenation

2.5.4.1. halogen atom substituted for the OH group

2.5.4.1.1. produces alkyl halide

2.5.4.1.2. single product is formed using heat

2.5.5. Polymerization

2.5.5.1. alcohol monomers repeatedly added together

3. need 180 degrees and an acid catalyst

4. Phenols OH is always carbon 1 phenol

4.1. functional group

4.1.1. hydroxyl group attached to a benzene ring

4.2. Physical proerties

4.2.1. solubility

4.2.1.1. slightly soluble in water

4.2.2. state at room temperature

4.2.2.1. solids or oily liquids

4.2.3. properties

4.2.3.1. antiseptic: a substance that kills microorganisms on living tissue

4.2.3.2. disinfectant is a substance that kills microorganisms on an inanimate objects

4.3. Chemical properties

4.3.1. flammible

4.3.1.1. cannot be dehydrated

4.3.2. can be oxidyzed with strong oxidizing agengts

4.3.2.1. weak acids in solution

4.4. Uses

4.4.1. 2% phenol is used as a surgical antiseptic

4.4.2. derivatives used as an antiseptic and a disenfectant

4.4.3. foods

4.4.3.1. used as an antioxidant

4.4.3.2. used as a peservatives

4.4.4. anaesthetic

5. Ethers oxy

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

5.2. ethers are produced through intermolecular dehydration of primary alcohols

5.3. Uses

5.3.1. MTBE is a gasoline additive

5.3.2. diethyl ether is was ageneral anaesthetic

5.4. Isomerism

5.4.1. constitutional isomers

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

5.5. Physical properties of ethers

5.5.1. solubility

5.5.1.1. more soluble in water than alkanes due to H-bonds with water

5.5.1.2. similar solubility to alcohols

5.5.2. Boiling point

5.5.2.1. similar to alkanes

5.5.2.1.1. lower then alcohols

5.6. Chemical properties

5.6.1. flamible

5.6.1.1. form explosives

5.6.2. unreactive with acids, bases, and oxidizing agents

5.6.3. good solvents due to there unreactivity

5.6.3.1. easy to remove after areaction

5.7. Cyclic ethers

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

5.8. Thiols

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

5.8.2. lower boiling points than alcohols

5.8.2.1. NO hydrogen bonds

5.8.3. strong and bad odour

5.8.4. easily oxidized to form disulfides R-S-S-R

5.8.4.1. important in protein structure (hair)

6. Carboxylic Acids

7. Amines

8. Aldehydes al

8.1. contain the carbonyl functional group C=O

8.1.1. polar bond with trigonal planar shape

8.2. have a carbonyl group at the end carbon ONLY

8.3. prepared by

8.3.1. oxidizing a primary alcohol with a mild oxidizing agent

8.3.1.1. removes 2 H atoms to form C=O

8.3.1.2. can be further oxidized to form a carboxilic acid by adding an oxygen atom

8.3.1.2.1. thus aldehydes must be protected from the air if you do not want further oxidation to occur

8.4. Simple aldehydes

8.4.1. Methanal

8.4.1.1. formed by oxidizing methenol an irritating gas carcinogenic to the skin

8.4.1.2. used to preserve biological speciments

8.4.2. Benzaldehyde

8.4.2.1. benzene ring attatched to methanal

8.4.2.1.1. gives almonds their flavour

9. What they both have in common

9.1. physical properties

9.1.1. boiling points

9.1.1.1. between alcohols and alkanes

9.1.1.2. higher boiling points than alkanes because C=O is polar thus dipole dipole atrtactions between the carbonyl groups

9.1.1.3. lower boiling points then alcohols because they can't H-bond between molecules

9.1.2. solubility

9.1.2.1. aldehydes and ketones H-bond with water so low molecular mass compounds are soluble in water

9.1.2.2. the longer the chain the less soluble or eventually insoluble they become

9.2. Uses

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

9.2.2. found widely in nature

9.3. Isomerism

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

9.4. Chemical reactions

9.4.1. Oxidation

9.4.1.1. only aldehydes will further oxidize

9.4.1.2. Tollens test (silver mirror) AgNO3 added to an aldehyde soution

9.4.1.2.1. positive test indicated by the oxidation of aldehyde to carboxylic acid and the reduction of Ag+ ions to silver metal, Ag

9.4.1.2.2. example of a redox reaction, where Ag is the oxidizing agent

9.4.1.3. Benedict's test (copper brick) solution of CuSO4 added to unknown solution

9.4.1.3.1. 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

9.4.1.3.2. example of a redox reaction where Cu2+ is the oxidizing agen

9.4.1.3.3. originally used to detect glucose in the blood and urine to diagnose diabetes

9.4.2. Reduction

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

9.4.3. Hemiacital formation

9.4.3.1. can be intermolecuar - to form a straight chain o rit can be an intramolecular reaction to form a cyclic hemiacital which are more stable

9.4.3.2. caused by a reaction of an aldehyde or ketone with an alcohol

9.4.3.2.1. 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

9.4.3.3. hemiacital is an alcohol group and ether group attached to the same carbon

9.4.4. Acetal formation

9.4.4.1. reaction of a hemiacital with another alcohol molecule

9.4.4.2. condensation reaction because there is a removal of water (still need an acid catalyst)

9.4.4.3. more stable

9.4.4.4. functional group is made up of 2 ether groups bonded to the same carbon

9.4.5. Polymerization

9.4.5.1. under acidic conditions phenol and formaldehyde monomers react to form phenol-formaldehyde network polymers

9.4.5.2. network polymers

9.4.5.2.1. monomers connected in a 3D cross-linked network

9.4.5.3. first man-made plastic was a phenol-formaldehyde polymer called makelite

9.4.5.3.1. today used as adhesive for plywood

10. Esters

11. Ketones one

11.1. prepared

11.1.1. through oxidation of seconday alcohols

11.1.1.1. with mild oxidizing agent to remove 2 hydrogen atoms to form C=O

11.1.1.2. 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

11.5.1.1. simplest ketone formed by the oxidation of 2-propanol

11.5.1.1.1. used as a solvent because it is soluble in both water and nonpolar subsances

11.5.1.2. byproduct of fat breakdown

11.5.1.3. component of nail polish remover

11.5.2. steroid hormones

11.5.2.1. testosterone, progesterone,and cortisone

11.5.3. sunscreens and sun-tannng agents