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Introductory Organic Chemistry I (Formerly CHM138H1)
University of Toronto St. George
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Browse the full collection of course materials, past exams, study guides and class notes for CHM136H1 - Introductory Organic Chemistry I (Formerly CHM138H1) at University of …

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Clive Scott Browning, Kristine Quinlan

Verified Documents for Clive Scott Browning, Kristine Quinlan

Class Notes

Taken by our most diligent verified note takers in class covering the entire semester.

CHM136H1 Lecture 2: Structure & Bonding

CHM136H1 Lecture 2: Intro to Organic Chemistry: January 9th

Positively charged nucleus (dense, protons and neutrons) Negatively charged electrons in a cloud around nucleus. Atomic number : number of protons in n

CHM136H1 Lecture Notes - Lecture 3: Trigonal Planar Molecular Geometry, Sigma Bond, Pi Bond

CHM136H1 Lecture Notes - Lecture 4: Chemical Polarity, Valence Electron, Lone Pair

CHM136H1 Lecture Notes - Lecture 5: Organic Chemistry, Electronegativity, Conjugate Acid

Resonance structures & acids & bases (lecture 5) Why do we use resonance structures there are molecules and ions that we can draw a single stru

CHM136H1 Lecture Notes - Lecture 6: Lone Pair, Conjugate Acid, Acid Strength

+1/-1 charge is ok, but try not to get larger than that pka values very useful for predicting potential acid-base reactions. A base will abstract a pro

CHM136H1 Lecture 7: lec 7 ecture 7:Alkanes & Their Stereochemistry

Noncovalent interactions (intermolecular forces, ie. between separate molecules) Dispersion especially important for non-polar molecules (instantaneous

CHM136H1 Lecture 8: Alkanes & their stereochemistry

CHM136H1 Lecture Notes - Lecture 10: Tetrahedron, Ring Strain, Cycloalkane

Cyclic compounds commonly encountered in all classes of biomolecules: Much less conformational freedom since the bonds cannot rotate. Stereoisomers sam

CHM136H1 Lecture Notes - Lecture 11: Cyclohexane Conformation, Cyclohexane, Ring Strain

Draw the two other resonance structures for ascorbic acid (vitamin c) When drawing resonance structures start with the atom with a charge. A more stabl

CHM136H1 Lecture 12: syubstituted cycloalkanes

Cyclohexane ring rapidly flips between chair conformations at room temperature for monosubstituted cyclohexanes, the two conformers are no longer equal

CHM136H1 Lecture 13: Intro to Stereochemistry

Chapter 5 (not 5. 10) & chapter 25 (25. 2 only) Isomers different compounds with the same molecular formula. Constitutional isomers isomers with di

CHM136H1 Lecture Notes - Lecture 14: Optical Rotation, Stereoisomerism, Atomic Number

CHM136H1 Lecture 15: Chirality

Rank atoms on each end of the bond by decreasing atomic number. If the first atoms in the substituent are the same, look at the 2nd, the 3rd, until the

CHM136H1 Lecture Notes - Lecture 16: Prochirality, Racemic Mixture, Trigonal Planar Molecular Geometry

Meso compounds do not happen often in nature despite a chirality centre, the molecules is achiral. Very helpful for visualizing and for drawing mirror

CHM136H1 Lecture 17: Organic Reactions

Donor of electron pair (lewis base) lone pair or pi-bond. Acceptor of electron pair (lewis acid) polarized bond or empty orbital. *electron-rich nucleo

CHM136H1 Lecture Notes - Lecture 18: Reaction Intermediate, Activation Energy, Reaction Mechanism

CHM136H1 Lecture Notes - Lecture 22: Isomerization, Alkene, Stereoisomerism

Each halogen added pulls out a hydrogen must take this into account when determining degrees of unsaturation. Eg. making an ether/alcohol doesn"t matte

CHM136H1 Lecture Notes - Lecture 24: Electrophilic Addition, Sigmatropic Reaction

CHM136H1 Lecture Notes - Lecture 25: Syn And Anti Addition, Regioselectivity, Halogenation

CHM136H1 Lecture Notes - Lecture 26: Oxymercuration Reaction, Racemic Mixture, Syn And Anti Addition

Addition of water but without the need of a carbocation intermediate prevents shifting. For alkenes generally: oxymercuration reaction (two-step proces

CHM136H1 Lecture Notes - Lecture 27: Cyclopropane, Epoxide, Alkene

CHM136H1 Lecture Notes - Lecture 28: Halocarbon, Primary Alcohol, Bond Energy

Organohalide a compound containing a halogen atom covalently bonded to a carbon. Dichloromethane and chloroform important organohalide solvents. Proper

CHM136H1 Lecture Notes - Lecture 29: Prochirality, Stereoisomerism

If the carbonyl is not symmetrical, stereoisomers will be formed. Some similarities to grignard reagents but are based on copper instead of magnesium.

CHM136H1 Lecture Notes - Lecture 30: Leaving Group, Reaction Step, Nucleophile

Substitution leaving group substituted by a nucleophile. ** key difference is in the timing of bond-breaking and bond-forming steps ** Backside attack

CHM136H1 Lecture Notes - Lecture 31: Protic Solvent, Leaving Group, Hydrogen Bond

Better leaving groups are those which can accommodate the negative charge they must adopt (ie. give more stable anions) Generally, weaker bases (eg. co

CHM136H1 Lecture Notes - Lecture 32: Rate-Determining Step, Racemic Mixture, Carbocation

A pure sn1 reaction should give a racemic mixture. When the leaving group leaves, a planar carbocation is formed substrate can attack from either face.

CHM136H1 Lecture Notes - Lecture 33: Propyl Group, Alkene, Alkane Stereochemistry

Like substitution, the key difference between these two is the timing of bond-breaking and bond-forming steps. ** recall good nucleophiles are often go

CHM136H1 Lecture Notes - Lecture 34: Alkane Stereochemistry

CHM136H1 Lecture Notes - Lecture 35: Benzene, Chlorobenzene, Substitution Reaction

Aromaticity compounds were referred as aromatic because they were fragrant. Now, it refers to a class of compounds containing benzene and benzene-like

CHM136H1 Lecture Notes - Lecture 36: Lone Pair, Pyrrole, Aromaticity

While the molecule on the left is not aromatic, if we pull off one of the hydrogens on the lower most carbon, then we form a anion. There will be 6 del

CHM136H1 Lecture Notes - Lecture 37: Phenyl Group, Phenol, Protonation

CHM136H1 Lecture Notes - Lecture 38: Tosyl, Leaving Group, Primary Alcohol

Conversion of alcohol to alkyl halide proceeds via sn2 inversion of configuration. Can use either pbr3 or socl2 when converting a secondary or primary

CHM136H1 Lecture Notes - Lecture 39: Monochromator, Spectroscopy

Monochromator allows light of only one wavelength to pass at a time. Eventually, all the wavelengths go through but only one at a time. Infrared radiat