Chemistry & BioOrganic Chemistry I

Organic Chemistry Cheat Sheet — 1-page PDF

Functional groups, naming, resonance, acid-base, stereochemistry, mechanisms, alkenes, alcohols. The whole course on one dense, printable page for your midterm or final, with every formula typeset and worked examples where they help.

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For a specific exam: Organic Chemistry I Midterm 1 study sheet, Organic Chemistry I Final exam study sheet.

  • 1 pageUS Letter
  • 10 sections11 topics
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Preview of the one-page Organic Chemistry I cheat sheet: Functional groups, naming, resonance, acid-base, stereochemistry, mechanisms, alkenes, alcohols Cheat sheet locked
the whole course, one page

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The topics a typical Organic Chemistry I exam tests, all on the one page.

  • Functional groups
  • Nomenclature basics
  • Resonance and formal charge
  • Acid-base and pKa trends
  • Stereochemistry: chirality, R/S, E/Z
  • Conformations
  • SN1 vs SN2
  • E1 vs E2
  • Alkene addition reactions
  • Markovnikov vs anti-Markovnikov
  • Alcohol reactions

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01Functional Groups

Core groups

GroupGeneral formSuffix / prefix
alkaneC-C-ane
alkeneC=C-ene
alkyneC≡C-yne
alcoholR-OH-ol / hydroxy-
etherR-O-R'alkoxy-
aldehydeR-CHO-al / formyl-
ketoneR-CO-R'-one / oxo-
carboxylic acidR-CO2H-oic acid
esterR-CO2R'-oate
amineR-NH2-amine / amino-
halideR-Xfluoro-, chloro-, bromo-, iodo-
functional group
Atom/group that controls major reactivity; naming priority often follows this group.
hydrocarbon
Molecule containing only C and H.
saturated
Only C-C single bonds.
unsaturated
Contains or .
  • Alkyl = substituent from alkane minus one H, e.g. methyl , ethyl .
  • Aromatic ring: phenyl .
  • Alkene/alkyne reactions occur at bond.

02Resonance

Resonance rules

RuleMeaning
move only e / lone pairsno atom movement
major formscomplete octets, more bonds, less charge separation
negative charge on more electronegative atomO > N > C
equivalent formsequal contributors

CarboxylateWhy is acetate stabilized?

Two equivalent resonance forms delocalize charge over both O atoms; bond order intermediate.

Watch out:Formal charges must sum to overall charge; draw all lone pairs before computing FC.

03Acid-Base

pKa

Lower = stronger acid.

Equilibrium

For .

Acidity trends

More acidic when...Reason
more electronegative atom bears chargestabilizes charge
larger atom bears charge down a groupcharge more diffuse
more resonance stabilizationdelocalization
greater -character in conjugate basesp > sp2 > sp3
electron-withdrawing groups nearbyinductive stabilization

04Stereochemistry

E/Z

Z: higher-priority groups on same side E: opposite sides

For alkenes using CIP priorities on each alkene carbon.

QuickAn alkene with highest-priority groups same side?

.

Watch out:Do not use cis/trans unless each alkene carbon has one identical substituent and geometric naming is unambiguous.

05Conformations

conformation
Different spatial arrangement from rotation about bonds; interconvert without bond breaking.

Ethane / butane

ConformationStability
staggeredlowest torsional strain
eclipsedhighest torsional strain
anti butanelowest; bulky groups apart
gauche butanehigher; bulky groups apart

Strain

torsional + steric + angle strain

Contributes to conformational energy.

ChairCyclohexane substituent most stable position?

Equatorial usually preferred; axial has 1,3-diaxial interactions.

06Elimination

Zaitsev

more substituted alkene major

Typical E1/E2 product unless bulky base or constrained geometry.

Hofmann

less substituted alkene favored

Often with bulky base or quaternary ammonium leaving group.

Anti-periplanarE2 requirement?

-H and leaving group must be anti-periplanar for best overlap.

Watch out:E2 needs a strong base; E1 often competes with SN1 under solvolysis conditions.

07Alkene Addition

Common additions

ReagentsOutcomeRegio / stereo
HXalkyl halideMarkovnikov
H2O, acidalcoholMarkovnikov
X2vicinal dihalideanti addition
X2, H2OhalohydrinOH on more substituted C
BH3 then H2O2/NaOHalcoholanti-Markovnikov, syn
H2, Pd/Calkanesyn hydrogenation

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Naming

  • Parent chain
  • Order
  • Common suffix priority

Resonance

  • resonance structures
  • Formal charge

Acid-Base

  • Hybridization acidity

Stereochemistry

  • chirality
  • enantiomers
  • diastereomers
  • CIP priority

Conformations

SN1/SN2

  • Key comparison
  • SN1
  • SN2

Elimination

  • E1 vs E2

Alkene Addition

  • Markovnikov
  • Anti-Markovnikov

Alcohols

  • Major reactions
  • Alcohol substitution

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FAQ

Questions

About the Organic Chemistry I sheet and making your own.

What does this Organic Chemistry I cheat sheet cover?
It has 10 sections: Functional Groups, Naming, Resonance, Acid-Base, Stereochemistry, Conformations, SN1/SN2, Elimination, Alkene Addition and Alcohols. Together they cover the topics a typical Organic Chemistry I exam tests, including functional groups, nomenclature basics, resonance and formal charge and acid-base and pKa trends.
Is the organic chemistry cheat sheet free?
The first part is free to read on this page, with no account needed. The full sheet opens in the app with Unlimited ($4.99 a month or $19 for a semester), where you can edit it, print it or save it as a PDF. It is one US Letter page and prints cleanly in black and white or colour.
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