Gr. 12 Organic Chemistry Cheat Sheet

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Science Chemistry Organic Reactions Highschool Gr-12 Imfs Nomenclature

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Introduction

The term organic generally means "something made from the earth" or "not chemically synthesized."

Organic chemistry refers to the study of compounds that contain carbon atoms as the principal element.

The simplest organic compounds are hydrocarbons made from C and H atoms

Despite the term organic generally meaning "natural," organic compounds can in fact be chemically synthesized (first synthesized organic compound was urea - found in mammal urine)

Carbon has a bonding capacity of 4 so each C atom must always make 4 bonds within a compound

General Nomenclature

Usual follows order prefix + root + suffix
Prefix	Indicates name/multiplying prefixes/position of branches
Root	Indicates number of carbons in the parent chain
Suffix	Indicates the parent chain's functional group

Root Name/Branch Prefixes

Number of C atoms / branches	Root prefix	Multiplying prefix
1	meth-	mono-
2	eth-	di-
3	prop-	tri-
4	but-	tetra-
5	pent-	penta-
6	hex-	hexa-
7	hep-	hepta-
8	oct-	octa-
9	non-	nona-
10	dec-	deca-

Special nomenclature prefixes: See Importance of Functional Groups, Haloalkyl/Other Functional Groups, and Special Alkyl Branches

All prefixes are listed in alpha order when writing the name of an organic compound, except for cyclo- and iso-.

Importance of Functional Groups

Functional Group	Suffix if Highest Precedence	Prefix if Lower Precedence
RC(=O)OH (carboxylic acid)	-oic acid ²	carboxy-
RC(=O)OR' (ester)	[branch]¹-yl [root]¹-oate	alkoxycarbonyl-
RC(=O)ON(R')R" (amide)	-amide	carbamoyl-
RC≡N (nitrile)	-nitrile	cyano-
RC=O (aldehyde)	-al ³	oxo-³
RC(=O)R' (ketone)	-one	oxo-
R(OH)R' (alcohol)	-ol	hydroxy-
R(N(R')R")R'" (amine)	-amine	amino-
RC=CR' (alkene)	-ene ⁴	Always used as a suffix
RC≡CR' (alkyne)	-yne ⁴	Always used as a suffix
RCCR' (alkane)	-ane	Always used as a suffix
R(X)R'	Always used as a prefix	See Haloalkyls/Other Functional Groups

^[1][branch] and [root] refer to the length of the carbon group's prefix (meth-, eth-, prop-, etc.)
^[2]If the carbon in the RCOOH group is not the parent chain, the highest precedence suffix is -carboxylic acid
^[3]If the carbon in the RCO group is not the parent chain, the highest precedence suffix is -carbaldehyde, and the alternate prefix is formyl-
^[4]If a compound is both an alkene and an alkyne, both -ene and -yne are used

Haloalkyls/Other Functional Groups

Functional Group	Prefix
R-O-R' (ether)¹	[branch]-oxy-
R-C-R (cycloalkyls)	cyclo-
R-F	fluoro-
R-Br	bromo-
R-Cl	chloro-
R-I	iodo-
R-NO`2`	nitro-
1,2-[branch(es)]²	ortho-[branch(es)]
1,3-[branch(es)]²	meta-[branch(es)]
1,4-[branch(es)]²	para-[branch(es)]

^[1]Ethers take precedence in prefixes over all other prefixes, except the branches attached to the ether group
^[2]Applies only to benzene ring branches

Special Alkyl Branches

Propyl	Butyl
n-propyl (normal)	n-butyl (normal)
isopropyl (y-shape)	isobutyl (y-shape)
	sec-butyl (2^nd C)
	tert-butyl (t-shape)

Alkanes

Contain only single bonds between C atoms
General chemical formula	C`n`H`2n+2` (n = whole number)
Odour	Odourless
Polarity	Non-polar (only C-H bonds)
Solubility in water	Slightly soluble
Boiling/melting point	Depends on length of parent C chain (more C = BP, less C = BP)

Alkenes

Contain at least one double bond between C atoms
General chemical formula	C`n`H`2n` (n = whole number)
Odour	Almost odourless
Polarity	Non-polar (only C-H bonds)
Solubility in water	Slightly soluble
Boiling/melting point	Depends on length of parent C chain (more C = BP, less C = BP)

Alkynes

Contain at least one triple bond between C atoms
General chemical formula	C`n`H`2n-2` (n = whole number)
Odour	Almost odourless
Polarity	Non-polar (only C-H bonds)
Solubility in water	Slightly soluble
Boiling/melting point	Depends on length of parent C chain (more C = BP, less C = BP)

Cycloalkyl

Alkane/alkene/alkyne where the C atoms are joined in a ring shape
General chemical formula	C`2`H`2n` (cycloalkane) C`2`H`2n-2` (cycloalkene) C`2`H`2n-4` (cycloalkyne) (n = whole number)
Odour	Odourless/almost odourless
Polarity	Non-polar (only C-H bonds)
Solubility in water	Slightly soluble
Boiling/melting point	Depends on length of parent C chain (more C = BP, less C = BP)

Alcohols

Any compound that contains a hydroxyl (R(-OH)-R') group
General chemical formula	C`n`H`2n-1`OH (n = whole number)
Odour	Slightly pungent
Polarity	Polar (between O-H bonds); longer C chains decrease in polarity
Solubility in water	Very soluble; longer C chains decrease solubility
Boiling/melting point	Depends on length of parent C chain (more C = BP, less C = BP)

Aldehydes/Ketones

Any compound that contains a carbonyl (R-C(=O)-R') group
Aldehydes have the carbonyl group at the first and/or last C atom of the molecule
Ketones have the carbonyl group in the middle C atom(s) of the molecule
General chemical formula	C`n`H`2n`O (n = whole number)
Odour	Pungent (aldehyde) Sweet (ketone)
Polarity	Polar (between C=O bonds); longer C chains decrease polarity
Solubility in water	Very soluble; longer C chains decrease solubility
Boiling/melting point	Very high, increases with length of parent C chain (more C = BP, less C = BP)

Carboxylic Acids/Esters

Any compound that contains a carboxyl (R-C(=O)-O-R') group
Carboxylic acids have the carboxyl group at the first and/or last C atom of the molecule
Esters have the carboxyl group in the middle C atom(s) of the molecule
General chemical formula	C`n`H`2n`COOH (n = whole number)
Odour	Unpleasant (carboxylic acid) Pleasant (ester)
Polarity	Polar (between C=O bonds); longer C chains decrease polarity
Solubility in water	Very soluble; longer C chains decrease solubility
Boiling/melting point	Very high, increases with length of parent C chain (more C = BP, less C = BP)

Ethers

Any compound that contains an alkoxy (R-O-R') group
General chemical formula	C`n`H`2n+2`O (n = whole number)
Odour	Slightly pungent
Polarity	Polar (between C-O bonds); longer C chains decrease polarity
Solubility in water	Very soluble; longer C chains decrease solubility
Boiling/melting point	Depends on length of parent C chain (more C = BP, less C = BP)

Amines/Amides

Any compound that contains a N atom in a carboxyl or carbonyl group
Amines have N atoms in a carbonyl group(s) (R-C(-N(-R')-R")-R'")
Amides have N atoms in a carboxyl group(s) (R-C(=O)-N(-R')-R")
General chemical formula	C`n`H`2n-1`NO (n = whole number)
Polarity	Polar (between C=O, C-O and C-N bonds); longer C chains decrease polarity
Solubility in water	Very soluble; longer C chains decrease solubility
State @ SATP	Depends on length of parent C chain (more C = more solid, less C = more gas)

Intermolecular Forces (IMFs)

Forces that occur between molecules
Influence the physical properties of a substance
Weaker than intramolecular forces (forces within molecules)
3 main types:
London Dispersion Forces (LDF)	Very weak forces that exist in all atoms/molecules caused by temporary charges due to e¯ shifts; become stronger with more e¯
Dipole- Dipole	Attraction between opposite charges of polar molecules; main reason for difference in melting/boiling points
Hydrogen bonding	Strong dipole-dipole forces with H atoms covalently bonded with an N, O or F atom
Strength of forces: (weakest) LDF Dipole-dipole H-bonding (strongest)

Combustion Reactions

All hydrocarbons burn with oxygen gas (alkanes/alkenes/alkynes/alcohols)
Combustion of hydrocarbon	C`x`H`y` + O`2` CO`2` + H`2`O
Combustion of alcohol	C`x`H`y`OH + O`2` CO`2` + H`2`O

Elimination Reactions

Take away 2 atoms to form double bond or H`2`O
Also called condensation/dehydration reactions
Elimination of haloalkyl	C`x`H`y`X`z` + [strong base] C`x`H`y-1` + [halogen (X) salt] + H`2`O
Elimination of alcohol	C`x`H`y`OH [conc acid] C`x`H`y-1` + H`2`O

Substitution Reactions

Replace one atom with another
Substitution reaction	C`x`H`y` + X`2` [heat/pressure] C`x`H`y-1`X + HX
Benzene rings
Benzene does not have true double bonds, so only substitution reactions can be performed
Benzene substitution	C`6`H`6` + X`2` C`6`H`5`X + HX
Benzene halide substitution	C`6`H`5`X + X`2` C`6`H`4`X`2` + HX
Halogen in benzene halide reactions forms product meta position only (1,3-[X]benzene)

Addition Reactions

Add atoms across double/triple bond
Alkenes/alkynes are nucleophiles (they like to give up e^_)
Hydrohalogenation	C`x`H`y` + HX C`x`H`y+1`X
Halogenation	C`x`H`y` + X`2` C`x`H`y`X`2`
Hydrogenation	C`x`H`y` + H`2` C`x`H`y+2`
Hydration	C`x`H`y` + H`2`O C`x`H`y+1`OH
Markovnikov's Rule: "the rich get richer"
The H atom of water/hydrogen gas/hydrogen halide will always bond with the C atom that already had more H atoms bonded to it in an addition reaction

Redox Reactions

Oxidation
C atoms will form more bonds to O atoms
Occurs when an organic compound reacts with an oxidizing agent (usually KMnO`4`/K`2`Cr`2`O`7`)
Oxidation of primary alcohol	C`x`H`y`OH [O] C`x`H`y-1`O (aldehyde)
Oxidation of secondary alcohol	C`x`H`y`OH [O] C`x`H`y-1`O (ketone)
Oxidation of tertiary alcohol	C`x`H`y`OH [O] NO RXN
Oxidation of aldehyde	C`x`H`y`O + H`2`O [O] C`x`H`y-1`OH + H`2` (carboxylic acid)
Reduction
C atoms will form fewer bonds to O atoms
Occurs when an organic compound reacts with an reducing agent (usually H`2`/LiAlH`4`)
Hydrogenation (reduction of aldehyde)	C`x`H`y`O + H`2` [H] C`x`H`y+1`OH (primary alcohol)
Hydrogenation (reduction of ketone)	C`x`H`y`O + H`2` [H] C`x`H`y+1`OH (secondary alcohol)

Esterification/Hydrolysis of Esters

Esterification
Condensation reaction (forms H`2`O)
Catalyzed by concentrated H`2`SO`4` and high heat
Esterification	C`x`H`y`COOH + C`x`H`y`OH [H`2`SO`4`] C`2x`H`2y`CO`2` + H`2`O
Hydrolysis of Esters
Reverse reaction to esterification
Hydro = water, lysis = break
Hydrolysis of ester	C`2x`H`2y`CO`2` + H`2`O [H`2`SO`4`] C`x`H`y`COOH + C`x`H`y`OH

Remember: Ester is a party girl; she drank some alcohol and did some acid

Synthesis/Hydrolysis of Amides

Synthesis of Amides
Condensation reaction (forms H`2`O)
Synthesis of amide	C`x`H`y`COOH (carboxylic acid) + C`x`H`y`NH`2` (amine) C`x`H`y`ONH`2` (amide) + H`2`O
Hydrolysis of Amides
Reverse reaction to synthesis
Hydrolysis of amide	C`x`H`y`ONH`2` (amide) + H`2`O C`x`H`y`COOH (carboxylic acid) + C`x`H`y`NH`2` (amine)

Synthesis of Amines

Amines can be made from haloalkyls using ammonia as a starting reactant
Synthesis of primary amines	C`x`H`x`X + NH`3` C`x`H`y`NH`2` + HX
Synthesis of secondary amines	C`x`H`x`X + C`x`H`y`NH`2` C`2x`H`2y`NH + HX
Synthesis of tertiary amines	C`x`H`x`X + C`2x`H`2y`NH C`3x`H`3y`N + HX

Polymers

Large molecules that are composed of many repeated subunits called monomers
Created through polymerization
Examples include plastics, DNA, and proteins
Unique physical properties - checmically unreactive, flexible/mouldable/stretchable
Polymerization (addition - chain reaction of alkene)	C`x`H`y` + C`x`H`y`+ C`x`H`y`+ ... [C`x`H`y`]`n`
Polymerization (condensation with alcohol - polyester)	HOC`x`H`y`OH + HOOCC`x`H`y`COOH + ... [O`2`CC`x`H`y`O`2`C`x`H`y`O`2`]`n`
Polymerization (condensation with alcohol - polyamide)	H`2`NC`x`H`y`NH`2` + HOOCC`x`H`y`COOH + ... [NOCC`x`H`y`O`2`C`x`H`y`ON]`n`

Polymerization (condensation) need the reacting functional group(s) to be on both sides of the monomer(s) to be able to complete the chain reaction (-dioic acid, -diol, -diamine)

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