CHAPTER 2: Structure and Properties of Organic Molecules

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1 1 HAPTER 2: Structure and Properties of Organic Molecules Atomic Orbitals A. What are atomic orbitals? Atomic orbitals are defined by special mathematical functions called wavefunctions-- (x, y, z). Wavefunction, (Psi), mathematical description of size, shape, orientation When the (x, y, z) coordinates are substituted into the wavefunction, a number will be calculated. Amplitude may be positive or negative or zero (Node) The sign of does not indicate charge relates energy of an electron to a location 2 gives the probability of finding an electron at a certain location Each can hold a maximum of 2-electrons (Pauli Exculsion) The s orbitals

2 2 The p-orbitals If we place our finger exactly half way along the string and pluck again, the string vibrates, we observe a standing wave but the midpoint does not move. Linear combination of atomic orbitals (LAO) Adding orbitals between atoms Add atomic orbitals between atoms Molecular Orbitals Adding orbitals on the same atom Hybridization, Valence Bond Theory Molecular Orbital Theory A. Forming Molecular Orbitals 1. Sigma Orbital Overlap

3 3 b. (s-p) Sigma Overlap Involving P-Orbitals (as in H-F) c. P x -P x overlap (l 2 ) (sigma) (head-on p-orbital overlap) 2. Pi Bonding

4 4 Hybrid Atomic Orbitals For more complicated molecules than H 2, it quickly became apparent that bonding m.o. s could not be formed from simple atomic orbitals. For example, if bonding m.o. s in H 4 were formed from the carbon 2p orbitals, the bond would only be 90 o apart (because the 2p orbitals are 90 o apart). However, we know that H 4 is tetrahedral, and the actual bonds are o apart. To solve this problem we add functions on the same atoms. o o This forms lower energy (more stable) Hybridized orbitals that can then form covalent bonds. This theory is also known as Valence Bond Theory. Forming Hybrid Orbitals (Hybridization) A. sp hybridization EXAMPLE BeH 2 B. sp 2 Hybridization EXAMPLE: BH 3. sp 3 Hybridization EXAMPLE: H 4

5 5 How do we quickly identify hybridization? NH 3 H 4 H 2 O NO 3 - H 2 NH HH # sigma bonds # Lone Pairs Steric Number VSEPR Trig. Pyr. Tetrahedral Bent Trig. Bent Linear Plan. Hybridization sp 3 sp 3 sp 3 sp 2 sp 2 sp heck Point: Drawing omplex 3D Molecules with Orbitals

6 6 Hybridization and Bond Length p-orbitals project farther out from the nucleus than s orbitals. As the contribution of p-orbitals in a hybrid orbital increases, the hybrid orbital gets longer and projects farther from the nucleus. The length of a bond depends on the length of the orbitals used to make the bond. Molecule Hybridization %-s or p haracter 1.53A 1.10A H 3 H 2 H 2 H sp A 1.08A H 3 H H H sp A 1.06A H 3 H sp Isomers A. onstitutional Isomers onstitutional (or structural) isomers differ in their bonding sequence. B. Stereoisomers Stereoisomers differ only in the arrangement of the atoms in space.

7 7. Geometric Isomers (a type of stereoisomer) Restricted Rotation Around arbon-arbon Double Bonds and cylcoalkanes. Molecules cannot rotate freely around carbon-carbon double bonds because rotation would break the bond and that costs energy! Because rotation is not possible around carbon-carbon double bonds, some alkenes with the same formula and connectivity exist as geometric isomers: How to name geometric isomers To name an alkene as a cis or trans isomer: 1) Examine the four groups attached to the carbons of the alkene. Must have exactly two identical groups, Exactly one on each carbon. 2) ompare the relative locations of the two identical groups.

8 8 is/trans Isomers of Ring ompounds (yclic ompounds) Ring compounds also have restricted rotations around bonds. As a consequence, rings can exist as geometric (cis/trans) isomers. If we picture the ring as flat, with all the atoms of the ring lying in a plane, then the ring will have two faces (two flat sides). Requirements for cis/trans: o Exactly two substituent groups on sp 3 hybridized carbons in ring. o o Substituents do not have to be identical as in alkene nomenclature. If we have three or more substituents, then we cannot use cis/trans for rings. Polar ovalent Bonds (Quick Review) In a covalent bond, the more electronegative atom will pull a greater share of the electrons toward itself. Examples The dipole moment, depends on Strength depends on: (in debyes) o = 4.8 x (electron charge) x d(angstroms)

9 9 Intermolecular Forces (Listed in order from weak to strong IM) 1. London (Dispersion) Forces Instantaneous dipole moment due to the mobility of electrons. (usually requires lower temperatures). 2. Dipole-Dipole attraction (polar molecules) - Attraction of molecules due to their dipole moments 3. H-Bonding is a strong type of dipole-dipole attraction 4. Ion-Dipole Attraction between ion and oppositely charged end of a dipole (polar molecule). Na OH 2 5. Ion-Ion Attraction between two oppositely charged ions. (Na l - ) Solubility (ritical to understanding lab) Molecules with similar intermolecular forces will mix freely. (like dissolves like) Polar (ionic) Solute with Polar Solvent (Ex. H 3 OH misc in H 2 O) Nonpolar Solute with Polar Solvent

10 10 Summary of Organic Functional Groups I. Hydrocarbons Hydrocarbons contain only carbon and hydrogen atoms. Functional Group Alkane Representative Structure H H Representative ondensed Formula R H Description and Properties contains only H and single bonds all carbon atoms are sp 3 hybridized Alkene R H=H R contains a carbon-carbon double bond carbon-carbon double bond is also called an olefin Alkyne R R contains a carbon-carbon triple bond terminal alkyne has triple bond at end of chain with hydrogen attached internal alkyne has triple bond in middle of chain, no hydrogen attached contains a six-carbon ring with alternating double and single bonds Arene (Aromatic ring) Ar H or Ph H double bonds of an aromatic ring are not alkenes (they have different chemical behavior from alkene double bonds) benzene ring can be called a phenyl group when attached to a carbon compound

11 11 II. Alkanes with Single Hydrogen Substitutions These functional groups are derived from alkanes that have a hydrogen replaced by another non-carbon atom. Alkane carbon: a carbon that is sp 3 hybridized and has only carbon or hydrogen atoms directly attached to it Functional Group Representative Structure Representative ondensed Formula Description and Properties Alcohol OH R OH contains an OH group attached to an alkane carbon an OH is called a hydroxyl group Ether O R O R contains an oxygen with two alkane carbons attached Amine N R NH 2 R NHR R NR 2 contains a nitrogen with 1, 2, or 3 alkane carbons directly attached all carbons attached to nitrogen must be alkane carbons Alkyl Halide X R X contains an alkane carbon with a halogen atom (F, l, Br, or I) directly attached halogen atoms are often represented by the symbol X halogen must be attached to an sp 3 hybridized carbon

12 12 II. arbonyl ompounds These functional groups contain a carbon-oxygen double bond. arbon-oxygen double bond is called a carbonyl group. Functional Group Aldehyde Representative Structure O H Representative ondensed Formula R HO Description and Properties contains a carbonyl group with 1 or 2 hydrogen atoms directly attached O Ketone R (O) R contains a carbonyl carbon with only carbon atoms directly attached contains a carbonyl group with a hydroxyl group (OH group) directly attached arboxylic acid O OH R OOH R O 2 H the OH group of a carboxylic acid is not an alcohol OH, and a carboxylic acid is not the same as an alcohol the hydrogen of the OH is acidic and is donated in a Bronsted-Lowry acid-base reaction contains a carbonyl with an O R group attached Ester O OR R O 2 R can be seen as a carboxylic acid where the OH hydrogen has been replaced by a carbon group esters are much less acidic than carboxylic acids Amide O N R ONH 2 R ONHR R ONR 2 contains a carbonyl with a nitrogen atom directly attached the nitrogen atom can have 0, 1, or 2 additional carbon groups attached

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