Organic Chemistry Core Concept Master Cheat Sheet

Organic Chemistry, 1 of 6
01: General Chemistry Review 03: Organic Nomenclature I
• Electron configuration: Using the number of electrons, IUPAC for Alkanes, Alkenes, Alkynes, and Alkyl Halides
follow the arrow from the bottom. 1. The longest continuous carbon chain is the parent
compound.
7s 2. Use “ane” for alkane, “ene” for alkene, and “yne” for
alkyne.
6p 6d
3. Circle the carbon chain to aid in identifying the parent
6s
compound.
4. Number the carbon chain in alkenes and alkynes so that
5s 5p 5d 5f
the multiple bonds have the lowest number, then number
s=2
the substituents.
4s 4p 4d 4f 5. For alkanes, number from whichever end that gives the
p=6
substituents the lowest possible combination of numbers.
3s 3p 3d d = 10 6. Give the location of each substituent with a number.
7. Use numerical prefixes for more than one identical group.
f = 14
2s 2p 8. Use “yl” on alkyl prefixes and “o” on halogen prefixes.
9. Alphabetize the groups, ignoring all numerical prefixes.
10. For alkenes, use cis if same groups are on the same side
1s
or trans if the same groups are on different sides.
Common for Alkanes and Alkyl Halides
• Hybridization: Determined by sigma bonds and • n Prefix: The structure is a straight chain, with the halogen
nonbonding electron pairs around one atom. on the end.
ƒ 2 sigma bonds and 0 nonbonding electron pairs = • iso Prefix: The structure contains two methyls attached to
sp, linear, 180o. CH, with functional group on the other end.
ƒ 3 sigma bonds and 0 nonbonding electron pairs = • sec Prefix: The halogen is attached to secondary carbon;
sp2, trigonal planar, 120o. use only if total number of carbons is four.
ƒ 4 sigma bonds and 0 nonbonding electron pairs = • tert Prefix: The halogen is attached to tertiary carbon; use
sp3, tetrahedral, 109.5o. only if total number of carbons is four or five.
ƒ 3 sigma bonds and 1 nonbonding electron pairs = • neo Prefix: The halogen is attached to a carbon and that
sp3, trigonal pyramidal, 107o. carbon is attached to tert-butyl group.
ƒ 2 sigma bonds and 2 nonbonding electron pairs =
sp3, bent, 105o.
04: Organic Nomenclature II
IUPAC Nomenclature Rules for Alcohols, Ethers,
Aldehydes, Ketones, Carboxylic Acids, and Amines
02: Introduction to Organic Chemistry 1. The longest continuous carbon chain is the parent
• Alkane: Contains a carbon-carbon single bond. compound.
• Alkene: Contains a carbon-carbon double bond. 2. Circle the carbon chain.
• Alkyne: Contains a carbon-carbon triple bond. 3. Number the chain so that the C-O bond has the lowest
• Aromatic: Contains a six-membered ring, with alternating possible number.
double and single bonds. 4. From the alkyl prefixes, use “anol” for alcohols and “ane”
• Alkyl Halide: Contains an alkyl and a halogen, RX. for ethers.
• Alcohol: Contains a ROH. 5. For ethers, the longest carbon chain is the parent
• Ether: Contains a ROR. compound and use “oxy” for the substituent group.
• Thiol: Contains RSH. 6. Give the location of the C-O bond with a number.
• Sulfide: Contains a RSR. 7. From the alkyl prefixes, use “anal” for aldehydes, and
• Aldehyde: Contains a H bonded to a C on one side of a “anone” for ketones.
C=O and a R or H bonded to a C on the other side. 8. From the alkyl prefixes, use “anoic acid” for carboxylic
• Ketone: Contains 2 R groups attached to the C on either acids and “anamine” for amines.
side of a C=O. 9. For amines, give the location of the attachment of the N
• Acid Halide: Contains a C=O, with an X attached to the C to the parent amine and number the groups attached to
on one side and an R or H attached on the other side. N.
• Carboxylic Acid: Contains a COOH, with an R or H 10. Give the location of each substituent with a number.
attached to the C of the COOH. 11. Use numerical prefixes if more than one identical group is
• Ester: Contains a COO, with an R attached to the O and a present
H or R attached to the C. 12. Alphabetize the groups, ignoring all prefixes.
• Anhydride: Contains an OCOCO, with an R or H attached IUPAC Nomenclature for Carboxylic Acids and
on either side of the O. Derivatives
• Amine: Contains an N, with R and / or H attached to N. 1. An ester is named as an alkyl alkanoate.
• Amide: Contains a N attached to the C of a C=O, with H 2. An anhydride is named as an alkanoic alkanoic anhydride.
or R on the other positions. 3. An acid halide is named as alkanoyl halide.
• Nitrile: Contains a carbon nitrogen triple bond. 4. An amide is named as an alkanamide. Any group
• Arrhenius Acid: Dissociates to give H3O+. attached to the N is numbered as “N.”
• Arrhenius Base: Dissociates to give –OH. Common Nomenclature Rules for Alcohols, Ethers,
• Bronsted-Lowry Acid: Donates an H+. Ketones, and Amines
• Bronsted-Lowry Base: Accepts an H+. 1. Use common prefixes, if needed.
• Lewis Acid: Accepts electron pairs to form new bonds. 2. An alcohol is named as an alkyl alcohol.
• Lewis Base: Donates electron pairs to form new bonds. 3. An ether is named as an alkyl alkyl ether.
4. A ketone is named as an alkyl alkyl ketone.
5. An amine is named with the alkyl groups, then “amine.”

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Organic Chemistry Core Concept Cheat Sheet

Organic Chemistry, 2 of 6
05: Drawing Organic Structures 07: Stereochemistry
Types of Structures Assigning Configuration for a Chiral Center
• Lewis Structure: All individual bonds are shown.
H Br H H CO 2H

H C C C C H 1. Find the chiral center

HO
H 4 different groups on carbon
H H H H
• Condensed Structure: Atoms are bonded to a central CO 2H
atom are listed after the atom. 2
Br 2. Assign priority to the groups
HO OH>CO 2H>CH 3>H
H 3
CH CH3 1
H3 C CH2 4
• Skeletal Structure: Carbon atoms are assumed to be
where two lines meet or at the end of the line. Hydrogens 2
are not shown. CO 2H
Br 3. Orient lowest priority in back
H H in this case
3 OH
1
• Sawhorse Structure: The drawing is looking down a
carbon-carbon bond.
CH3
2 CO 2H
C
H Br
4. Trace from high to low
Clockwise, assign R
CH3 H
Counterclockwise, S
3 OH
C 1
H H

06: Alkanes and Cycloalkanes 08: Conformational Analysis

Reactions of Alkanes Conformations for Ethane
• Combustion converts alkanes to carbon dioxide and water.
The formula is based on n, the number of carbons. H H H
H H
H
CnH(2n+2) + 3n + 1 O2 nCO2 + (n+1) H2O
H H

2 Ξ H
H Ξ
H H
• Cracking of hydrocarbons at high temperatures yield a H H H H
H H
mixture of smaller alkanes and alkenes.
heat staggered
Rotate about
large alkane smaller alkanes + alkenes C-C bond H
catalyst H H H H
• Halogenation of alkanes occurs with halogen in the
H H
presence of heat or light and through a radical mechanism. Ξ H Ξ H
heat or H H
H H H H H
R-H + X2 R-X + H-X
H H
light
eclipsed
o In initiation, radicals are formed.
heat or Conformations for Butane
Cl2 2 Cl
light CH3 H CH3 CH3 H3C CH3
H H H3C H
o In propagation, radicals are consumed and radicals H H
are formed. H H H H H H H H
H3C H
CH3 H
CH3CH3 + Cl CH3CH2 + HCl eclipsed gauche
staggered eclipsed
staggered
CH3CH2 + Cl2 CH3CH2Cl + Cl
H CH3
o In termination, the radical are consumed. H H H3C H

CH3 H3C H CH CH3 H H CH

CH3CH2 + CH3CH2 CH3CH2CH2CH3 CH3 3 H
3

Cl + Cl Cl2
H H H H H H
H H

CH3CH2 + Cl CH3CH2Cl
Lowest energy Highest energy
ANTI ECLIPSED

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Organic Chemistry Core Concept Cheat Sheet

Organic Chemistry, 3 of 6
09: Alkyl Halides: Nucleophilic Substitution 11: Alcohols and Ethers
and Elimination Reactions of Alcohols
Substitution Unimolecular Unimolecular, SN1 • Reaction with metal. Product = alkoxide.
• Slow step = bromide takes the electron pair and departs as • Reaction with HX, PCl3, or PCl5. Product = alkyl halide.
leaving group. • Dehydration.
H H
• Carbocation is formed. H+
H3C H
• Faster step = rearrangement, if present. H3C C C H C C
• Fast step = weak nucleophile attacks the carbocation from heat
CH3 OH H3C H
both sides.
o o
• Nucleophile abstracts the extra proton from the product • Oxidation of 0 and 1 alcohols with PCC.
and the electron pairs move from O-H bond to O. H
Substitution Bimolecular, SN2 PCC H3 C H
H3 C C H C
• Nucleophile attacks on the carbon, but on the opposite side
of the halogen.
OH O
• Bromide takes its electron pair and leaves.
• Oxidation of 0o and 1o alcohols with Na2Cr2O7, K2Cr2O7,
• In the intermediate, the nucleophile and leaving group are
KMnO4, NaOCl, HNO3, or CrO3.
drawn 180o apart. H
Elimination Unimolecular, E1 NaOCl H3C OH
• Bromide takes the electron pair and departs as the leaving H3C C H C
group, a carbocation is formed.
• Slow step = formation of carbocation. OH O
• Weak base abstracts hydrogen on carbon next to • Oxidation of 2o alcohols with Na2Cr2O7, K2Cr2O7, KMnO4,
carbocation, then electron pair goes from C-H bond to C-C NaOCl, HNO3, CrO3, or PCC.
bond to form double bond. H
Elimination Bimolecular, E2 CrO3 H3C CH3
• Strong nucleophile abstracts proton from carbon adjacent H3 C C CH3 C
to carbon with X, but on opposite side from X = anti H2SO4
elimination. OH O
• C-H electrons go to C-C bond to form double bond. • Esterification.
O O
• C-Br bond electrons go to Br.
H+
• Br leaves with electron pair. CH3CH2OH + C + H OH
C
10: Alkenes, Alkynes, and Dienes H3C OH H3C OCH2CH3
Synthesis of Alkenes 12: Aromatic Compounds, Aromaticity and
• Dehydrohalogenation of Alkyl Halides
H H Reactions
H3C H
KOH Reactions of Benzene
H3C C C H C C • Reaction with Br2, FeBr3; Cl2, AlCl3; or I2, HNO3. Product =
halobenzenes.
CH3 Br H3C H Br
• Dehydration of Alcohols Br2
H H
H3C H
H+ FeBr3
H3C C C H C C
heat
• Reaction with HNO3 + H2SO4. Product = nitrobenzenes.
CH3 OH H3C H NO2
HNO3
Reactions of Alkenes
• Addition of hydrogen halide. Product = alkyl halides. H2SO4
H3 C H CH3 H
HCl • Reaction with with SO3 + H2SO4. Product = benzenesulfonic
C C H3 C C C H
acids.
H3 C H SO3H
Cl H
SO3
• Halogenation. Product = dihaloalkanes.
H3 C H CH3 Cl
H2SO4
Cl2
C C H3 C C C H • Reaction with AlCl3 and RX. Product = alkylbenzenes.
CH2CH3
H3 C H Cl H
AlCl3
• Hydration. Product = alcohols.
H3 C H CH3 H CH3CH2Cl
H2O
C C H3 C C C H • Reaction with AlCl3 and an acid halide. Product = ketones.
+ O O
H3 C H H OH H
• Hydrogenation. Product = alkanes. C C
H3 C H CH3 H CH3CH2 Cl CH2CH3
H2
C C H3 C C C H AlCl3
Pt
H3 C H H H

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Organic Chemistry Core Concept Cheat Sheet

Organic Chemistry, 4 of 6
13: Aldehydes and Ketones 15: Carboxylic Acids and Derivatives
Reactions of Aldehydes and Ketones Reactions of Carboxylic Acids
• With RLi or RMgX, followed by acid. Product = alcohols. • Carboxylic acids + LiAlH4, then H3O+. Product = alcohols.
H3C H CH2CH3 CH2CH3 CH3CH2 OH
CH3CH2MgCl 1. LiAlH4
C H3O+ C CH3CH2 CH2 OH
H3C C H H3C C H 2. H3O+
O O
OMgCl OH • Carboxylic acids + SOCl2. Product = acid halides.
• With H2 and Ni; LiAlH4; or NaBH4. Product = alcohols. CH3CH2 OH CH3CH2 Cl
SOCl2
H C C + O=S=O
H3C H
1. LiAlH4
C + HCl
H3C C H O O
2. H3O + • Carboxylic acids + ROH + H+. Product = esters.
O
OH CH3CH2 OH CH3CH2 OCH3
CH3OH
• With Zn(Hg) + HCl or NH2NH2 + KOH. Product = alkanes. C C
H H+
CH3CH2 CH3 1. NH2NH2 O O + HOH
C CH3CH2 C CH3 • Carboxylic acids + acid halides. Product = anhydrides.
2. KOH, heat CH3 OH CH3 O CH3
CH3 Cl
O H C + C C C
• With ammonia derivatives and acid. Product = imines. + HCl
CH3 H CH3 O O O O
N N Reactions of Esters
H3C H
CH3NH2 -HOH • Esters + LiAlH4, then H3O+. Products = alcohols.
C H3C C H C CH3CH2 OCH3 1. LiAlH4
H+ H3C H C
O OH CH3CH2CH2OH + CH3OH
2. H3O+
• Aldehydes with Na2Cr2O7, K2Cr2O7, KMnO4, NaOCl, HNO3, or O
CrO3. Product = carboxylic acids. • Esters + amines. Products = amides + alcohols.
CH3CH2 H CH3CH2 OH CH3CH2 OCH3 CH3CH2 NHCH3
NaOCl
C C CH3NH2 C
C
+ CH3OH
O O O O

14: Enols and Enolates 16: Amines

• Ketones or aldehydes + X2 + H+ or ketones or aldehydes + Synthesis of Amines
X2 + OH-. Product = α-halo ketones or aldehydes. • Amides + LiAlH4, then H3O+. Product = amines.
Br H

CH3CH2 CH2CH3 CH3CH2 CHCH3 H3C N 1. LiAlH4

C Br2 C CH3
C CH3 CH2 NHCH3
2. H3O+
O H+ O O
• Haloform reaction: Methyl ketones + excess OH- + excess • Alkyl halides + amines, then loss of HX. Product = amines.
X2. Product = carboxylate anions + haloforms. CH3CH2Cl
CH3CH2CH2NH2 CH3CH2CH2NH2CH2CH3 Cl
CH3CH2 CH3 excess I2 CH3CH2 O
C C + CHI3 -HCl
excess OH- CH3CH2CH2NHCH2CH3
O O
• Aldehydes or ketones + (1) H2NOH + H+, (2) H2 + Ni; or
• Hell-Volhard-Zelinsky reaction: Carboxylic acids + PX3.
LiAlH4, then H3O+; or Zn + HCl. Product = 1o amines.
Product = α-halo carboxylic acids. CH3
CH3 H
Br
1. H2NOH, H+
CH3CH2 OH O C H C N
1. PBr3 CH3CH OH
C 2. H2, Ni
C CH3 CH3 H
2. H2O o +
O O • Aldehydes or ketones + (1) 1 amines + H , (2) H2 + Ni; or
• Haloform reaction: Methyl ketones + excess OH- + excess LiAlH4, then H3O+. Product = 2o amines.
CH3 H
X2. Product = carboxylate anions + haloforms. CH3
1. CH3CH2NH2, H+
CH3CH2 CH3 CH3CH2 O O C H C N
excess I2
C C 2. H2, Ni
+ CHI3 H H CH2CH3
excess OH- • Aldehydes or ketones + (1) 2o amines + H+, (2)
O O
• Hell-Volhard-Zelinsky reaction: Carboxylic acids + PX3. Na(CH3COO)3BH. Product = 3o amines.
H H
Product = α-halo carboxylic acids. CH3
Br 1. (CH3)2NH, H+
O C
H C N
CH3CH2 OH CH3CH OH 2. Na(CH3COO)3BH
1. PBr3 H
C H CH3
C
O 2. H2O
O

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Organic Chemistry Core Concept Cheat Sheet

Organic Chemistry, 5 of 6
17: IR and Mass Spectrometry 19: Understanding Organic Reactions
IR Problem Solving Reactions
• Calculate the unsaturation number and give interpretation. • Alkyl Halides
• Using the formula and interpretation of the unsaturation • Alkenes
number, predict possible functional groups present. • Alkynes
• Look for frequencies for the functional groups in the table. • Benzene
• Once all of the frequencies have been identified, draw the • Amines
structure. • Alcohols
Cleavage Reactions in a Mass Spectrum • Aldehydes and Ketones
• Alcohols dehydrate to yield alkenes and undergo α cleavage • Carboxylic Acids
of the C-C bond to form cations. • Acid Halides
• Esters
• Anhydrides
+ H2 O • Amides

H OH 20: Mechanisms of Organic Reactions

Addition to Carbonyl Compounds
C
• Reaction of Grignard reagents with aldehydes and ketones.
+ C C
• Reaction of aldehydes and ketones with primary amines.
H OH H OH OH Mechanisms of Acid-Base Reactions
• Amines undergo N-C cleavage and α cleavage of the C-C • Reaction of carboxylic acids with sodium hydroxide.
O O
bond to form iminium ions.
• Ethers undergo O-C cleavage and α cleavage of the C-C Na OH
C C
bond to form cations. CH3CH2 O H CH3CH2 O Na
• Aldehydes and ketones undergo C-C cleavage to form
acylium ions.
+ H OH
R • Reaction of amines with hydrogen chloride.
C R + C O C O H H
O CH3CH2CH2 N H Cl CH3CH2CH2 N H Cl
• Carbonyl compounds undergo McLafferty rearrangement to
form alkenes and enols. H
H
H
γ O OH
Carbocation Rearrangements
+ • 1,2-Hydride shift.
β C
CH3 CH3
α 1,2-hydride shift
H H3C C CH2 H3C C CH2
γ O OH faster
H H
+
β C o o
1 carbocation 3 carbocation
α
• 1,2-Alkyl shift.
18: NMR and Problem Solving CH3
CH3
1
H NMR Problem Solving 1,2-alkyl shift
1. Calculate unsaturation number and give interpretation. H3C C CH2 H3C C CH2
2. List the chemical shifts. faster
3. Compare to Proton Magnetic Resonance tables. CH3 CH3
4. List splitting.
5. Measure vertical distance of integration with ruler. 1o carbocation 3o carbocation
6. Add up integrations.
7. Determine multiplication factor by dividing H by sum of Anion Mechanisms
integrations. • Mechanism of carbonyl compounds with LDA.
8. Multiply each integration by multiplication factor to get H • Mechanism for addition of hydride ion.
per signal. H H
9. For interpretation, use calculated H that are adjacent to CH3 H H H
splitting minus 1. CH3 C H CH3 C H
C
10. Put the structure together, following the formula.
13 O OH
C NMR Problem Solving O
1. Calculate unsaturation number and give interpretation. Radical Mechanisms
2. List the chemical shifts. • Halogenation of alkanes.
3. List the splitting.
4. Give the interpretation of the splitting.
5. Give the interpretation by chemical shift.
6. Put the structure together.

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Organic Chemistry Core Concept Cheat Sheet

Organic Chemistry, 6 of 6
21: Writing Reaction Mechanisms 23: Carbohydrates
• Unshared pair to shared pair. Monosaccharides

H H CH3 H3C CH3

OH
H C C C H C C

H H Br H H

+ HOH + Br
• Shared pair to shared pair.
Disaccharides
H H CH3 H3C CH3
OH
H C C C H C C

H H Br H H

+ HOH + Br

• Shared pair to unshared pair.

Oligosaccharides
H H CH3 H3C CH3
OH
H C C C H C C

H H Br H H

+ HOH + Br

22: Amino Acids, Peptides, and Proteins

Structure of Amino Acids
Carboxyl group
24: Nucleic Acids
Amino gives the acidic Carbohydrate Classification
group gives nature for
the name – amino acid
amino acid
COOH
Are made up of

Hydrogen
α-carbon Sugar + Nitrogenous base + Phosphate group
H2N C H Called a Nucleotide

Purines Pyrimidines
Ribose Deoxy ribose
R
Present in
Carbon with four
a general letter used to refer any different types of RNA DNA Adenine Guanine
additional group attached to a atoms or groups of
carbon atom and it is often atoms attached to it
referred to as side chain in that is called a “chiral “
compound carbon
Cytosine Thymine Uracil
Peptide Bonds (present only in RNA)
CH3
H Types of Nucleotides
HNH COOH There are two types of nucleotides Ribonucleotide,
C
NH2 C COOH present in nucleic acids. They are present in RNA
+
deoxy- ribonucleotide & Ba
P P
H ribonucleotide P se
H
H2O
glycine alanine Sugar
unbound Nucleotide
boun monophosphate
d e.g. AMP,GMP
O O
H H
Nucleotide di P
P Ba
phosphate e.g.
ADP,GDP P

unbound Sugar
Nucleotide
triphosphate 2
e.g. ATP,GTP O H
H
Deoxyribonucleotide, present in DNA

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