Organic Chemistry

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Welcome to Organic Chemistry

• Definition of 'Chemistry' and 'Organic'
• Brief History of Organic Chemistry

Lewis Structures and Bonding

• Lewis Dot Diagram
• Dipoles
• Covalent Bonds
• Ionic Bonds

Hybridization and Atomic and Molecular Orbitals

• Atomic Orbitals and Periodic Table Relationships
• Molecular Orbitals and Hybridizations
• Drawing Atomic and Molecular Orbitals Diagrams for Molecules

Ways to Draw and Represent Molecules

• Skeletal Structure
• Condensed Structure
• Bond Line Notation

Resonance

• What is Resonance?
• Formal Charge
• Finding Resonance Structures
• Major and Minor Resonance Structures

Functional Groups

• Quick Introduction of Structures
• Memorization Tips and Tricks

Nomenclature

• Introduction to IUPAC Nomenclature
• Naming Carbohydrate
• Naming Functional Groups
• Naming Carboxylic Acid Derivatives
• Naming Aromatics

Newman and Fischer Conformational Analysis

• Sawhorse Projections
• Introduction to Newman Projections
• Newman Projection to Bond line Notation
• Bond Line Notation to Newman Projection
• Introduction to Fisher Projections
• Fischer Projection to Bond Line View
• Bond Line View to Fischer Projection

Cyclohexanes

• Drawing Cyclohexanes in Boat and Chair Conformations
• Axial and Equatorial Bonds
• Cyclohexane Chair Flip
• Conversions Between Molecule View and Chair View
• Steric Strain
• Homodesmotic Reactions

Stereochemistry (R and S), Isomers, and Optical Activity

• Introduction to Chirality and Chiral Centers
• Chiral and Achiral Molecules
• Finding R and S for Chiral Centers
• Finding R and S for Tricky Examples
• Enantiomers
• Diastereomers
• Meso Compounds

E and Z, Cis and Trans Alkenes

• Cis and Trans
• E and Z
• Cis and Trans, E and Z for Cyclic Compounds

Acids and Bases

• Main Characterstics or Lewis/Bronsted Definition
• Factors Determining Strength
• pH, pKa, Ka, pKb, Kb

Nuclear Magnetic Resonance (NMR)

• Electronegativity and Shielding
• Equivalent Hydrogens
• What NMRs Actually Tell Us
• Molecules to NMR
• Identifying Complex Splitting
• NMR to Molecule
• Carbon-13 NMR

Infrared Spectroscopy

• Infrared Spectroscopy
• Mass Spectometry
• Combined Analytical Methods

Alkene and Alkyne Addition Reactions

• Carbocation & Markovnikov's Rule
• Hydrohalogenation
• Halogenation
• Acid Catalyzed Hydration
• Acid Catalyzed Hydro-alkoxy Addition
• Hydration via Hydroboration-Oxidation
• Epoxidation
• Osmylation-OsO4 (Osmium Tetroxide)
• Ozonolysis
• Hydrogenation
• Introduction to Reactions and Mechanisms

Radical Reactions

• Homolytic v Heterolytic Cleavage
• Radical Stability
• Radical Halogenation of Alkanes
• Radical Halogenation of Alkenes (Antimarkovnikov)

Nucleophilic Substitution Reactions (SN1 and SN2) and Elimination Reactions (E1 and E2)

• Nucleophile vs. Base Strength
• Leaving Groups
• Polar Protic, Polar Aprotic and Non-Polar Solvents
• SN1 and SN2 Reactions
• Choosing between SN1 and SN2
• E1 and E2 Reactions
• Choosing between E1 and E2
• Comparing and Determing SN1 or SN2 and E1 or E2 reactions

Uncategorized Questions

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• Question #b741b
• How are covalent bonds represented in Lewis dot diagrams?
• Which is predicted to have the shorter sulfur–oxygen bonds, #SO_3# or #SO_3^(2-)# ?
• What is the structure of the functional group and the condensed formula for 3,4-dimethyl heptanoic acid?
• How can I draw accurate Newman projections?
• How can I interpret a Sawhorse projection?
• What do the dextro and levo prefixes mean in latin?
• Why are enantiomers important to the pharmaceutical industry?
• How could IR spectroscopy distinguish between #CH_3CH_2CH=CHCH_3# and #CH_3CH_2C≡C CH_3#?
• How does Markovnikov's rule work?
• Why is tertiary carbocation most stable?
• How are synthetic alkynes used to treat Parkinson’s disease?
• How many intermediates are there in the mechanism for the acid-catalyzed hydration of an alkene?
• What is chain propagation and termination in free radical halogenation?
• What is the leaving group in the hydrolysis of tert-butyl bromide with water forming tert-butanol?
• Question #d16ba
• Question #6e71b
• Question #d3e85
• What are casein and hemocyanin?
• Question #898eb
• Question #845d9
• What are the benefits of investigating shale-oil gas?
• What are the functional groups in polysaccharides?
• How does an enzyme lower the activation energy?
• Question #7fe21
• What is the energy profile in *cis*- and *trans*-1-bromo-4-methylcyclohexane?
• Question #ed0b9
• Question #42a55
• Question #cd765
• Question #1479e
• Question #8e357
• Why does hydrogen bonding occur in salicylic acid, and yet this acid is not particularly water-soluble?
• Question #1acbb
• Question #33c98
• Question #7cfbd
• Question #27ab2
• Question #dfce4
• How do you draw keto-enol tautomerization and enamine tautomerization mechanisms?
• Why are unsaturated fats preferred to saturated fats....?
• How can you use nucleophilic substitution to create an alkane from a halogenoalkane?
• Question #375f0
• Question #f2dad
• What is enthalpy of hydrogenation?
• How can I convert the bond-line structure of 2-methylhexane to a Newman projection viewed along the C3-C4 bond?
• What makes for a good leaving group?
• What is a Kováts retention index in gas chromatography, and how do I calculate it?
• Which one is more acidic? Acetone or acetaldehyde? Methyl acetate or acetone?
• Question #d7c12
• What is the advantage of alkylating using enamines instead of the enolate counterpart?
• Question #1d3f8
• Question #9327a
• Can someone help me in identifying enantiomer pairs, specially in carbohydrates (sugars)? Also, state an example.
• How do you identify #alpha# and #beta# forms in sugars?
• Can you give me the structure for 2,3,5-trimethylhepta-2,4,6-triene?
• Question #51b1b
• Question #96750
• Question #82512
• What are the effects of substituents on the reactivity of the molecule?
• Write complete mechanism of dehydration of 2-methyl-1-pentanol?
• What is the reagent and condition needed when cyclohexene produce chlorocyclohexane as a product?
• Give the structural formula of all alkenes produced from dehydration of the following alcohols.(i)butan-1-ol (ii)(CH3)3OH (iii)HOCH2CH(CH3)CH2CH3 (iv)CH3CH(OH)CH(CH3)2?
• Which amines form stronger bases:aliphatic or aromatic amines?
• What is the name of CH2=C(CH3)2?
• How to memorize and understand the mechanism in preparation and reactions of alkene?
• Draw the stepwise mechanism of hydrohalogenation of ethylenecyclopentane?
• Question #57aa3
• What is the iupac name for CH3CH2CH2CH2CH2- ?
• What do you mean by polar protic and polar aprotic solvents? What are some examples of these?
• What is the #E1# mechanism? Can you explain me the reaction for the dehydrohalogenation of tert-butyl chloride?
• Why is cyclopropane unstable?
• Question #b68a8
• Question #ff228
• Question #d44c2
• Why is the activation energy required to rotate the C-N bond in tertiary amides (i.e. N,N-dimethylacetamide) higher than for a primary amide (i.e. acetamide)?
• How to calculate the solubility of a racemic mixture if each enantiomer in the mixture has equal solubility values?
• Cyclohexene to ethyl cyclohexyl acetylene?
• How do you identify stereocenters on a complex molecule?
• How do you write the synthesis for the ozonolysis of styrene catalyzed by zinc, followed by acidification with potassium permanganate in strong acid, to yield two carboxylic acids?
• What are all the structural isomers of hexane?
• Question #aae38
• How does orbital hybridization occur in alkanes?
• How does hybridization affect electronegativity?
• Why is water used to quench a reaction involving lithium or Grignard reagents?
• Question #76b38
• Question #76b47
• Question #a56e9
• Question #182e9
• Why should you NOT turn off the tap of a water pump when you perform a suction filtration?
• Question #24d0b
• What is the difference between structural isomers, geometric isomers, and stereo isomers?
• What do the skeletal structures of C6H12 look like?
• Are #"magnesium phosphate/magnesium bromide"#, #"sulfuric acid/sodium bisulfate"# #"buffer solutions"#?
• What is the mutual solubility of isopropyl alcohol, water, and ethanol?
• How do you go from chloroform to methylacetylene in as few steps as possible?
• What is the organic molecule than stores the most energy called, and what is its structure?
• What are the product(s) for the #"S"_N1# reaction of 2-iodo-3-methylbutane with ethanol?
• What is an organic compound found in most cells?
• Combustion analysis of toluene, a common organic solvent, produces 2.93 mg of #CO_2# and .685 g of #H_2O#. The molecular mass is 46 g/mol. If the compound contains only carbon and hydrogen, what is the molecular formula?
• Question #9b926
• How do we account for unusual experimental results?
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