Chapter 1 Organic Chemistry
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- What is the normal bonding pattern for hydrogen?
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One valence electron.
One bond.
No lone pairs. - What is the normal bonding pattern for a halogen?
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7 valence electrons.
One bond.
6 lone pairs - What is the normal bonding pattern for nitrogen?
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5 valence electrons.
3 bonds
1 lone pair. - What is the normal bonding pattern for oxygen?
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6 valence electrons
2 bonds.
2 lone pairs. - What is the normal bonding pattern for hydrogen cation?
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1 bond
+1 charge
no lone pairs - What is the normal bonding pattern for hydrogen anion?
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1 bond
-1 charge
1 lone pair. - What is the normal bonding pattern for the carbocation?
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3 bonds
no lone pairs
+1 charge. - What is the normal bonding pattern for the carboanion?
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3 bonds
1 lone pair
-1 charge. - What is the normal bonding pattern for the C dot ion?
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3 bonds
1 single electron
no net charge. - What is the normal bonding pattern for the nitrogen cation?
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4 bonds
no lone pairs
+1 charge. - What is the normal bonding pattern for the nitrogen anion?
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2 bonds
2 lone pairs
-1 charge. - What is the normal bonding pattern for the oxygen anion?
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1 bond.
3 lone pairs.
-1 charge. - What is the normal bonding pattern for the oxygen cation?
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3 bonds.
1 lone pair.
+1 charge. - What is the normal bonding pattern for a halogen anion?
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0 bonds
4 lone pairs.
-1 charge -
What is the name of this functional group? - Alcohol
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What is the name of this functional group? - Aldehyde.
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What is the name of this functional group? - Carboxylic acid
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What is the name of this functional group? - Ether
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What is the name of this functional group? - Ketone
- What are isomers?
- Compounds that have the same molecular formula but different arrangements of bonding in their atoms.
- What are the two main types of isomers?
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1. Constitutional isomers.
2. Steroisomers. - What are constitutional isomers?
- Compounds with different connections between the atoms.
- What are stereoisomers?
- Compounds with same connections betwen the atoms but different arragement of atoms in space.
- What are the three different relevant types of orbitals for organic chemistry?
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1. S-orbitals
2. P- orbitals
3. D-orbitals - What are s-orbitals?
- Spherical in shape, they can only have 2 electrons in the orbital. 2s orbitals have 2 nodes, 3s orbitals have 3.
- What are p-orbitals?
- Dumbell shaped, 3 different spatial orientations, can only hold 2 in each lobe (for a total of 6 for all p-orbitals.
- What are d-orbitals?
- 4 Clovershaped, 1 dumbbell w/spherical center.
- What are the two different types of covalent bonding?
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1. sigma bond
2. pi bond - What is a sigma bond?
- A covalent bond where the electrons are centered about the axis between the two nuclei.
- What is a pi bond?
- A covalent bond where the shared electrons occupy regions above and below axis between two nuclei.
- What are hybrid orbitals?
- Orbitals where the wave function s of the different oribitals combine to form new orbitals.
- What is an sp-orbital?
- A combination of an s-orbital and a p-orbital.
- What is an sp2-orbital?
- A combination of an s-orbital and 2 p-orbitals.
- What is an sp3-orbital?
- A combination of an s-orbital and 3 p-orbitals.
- What are the four types of bonding?
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1. Ionic
2. Polar covalent
3. Non-polar covalent
4. Hydrogen - What is an ionic bond?
- Electrons are given away ... not shared and held together by +/- attractive force of the ions.
- What is a polar covalent bond?
- Shared electron bond where the electrons are strongly attracted to one element more than another.
- What is a non-polar covalent bond?
- Shared electron bond where the electrons are equally distributed about all elements.
- What is hydrogen bonding?
- An attractive interaction between a hydrogen atom bonded to an oxygen, nitrogen, or fluorine atom and an unshared electron pair on another atom.
- What is the trend in the Periodic Table for valence electrons?
- The group number is equal to the number of valence electrons for the element.
- What trends are associated with an elements position on the Periodic Table with respect to electronegativity?
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1. Electronegativity increases to the right in periods.
2. Electronegativity increases as you travel up the group. - What are the rules for drawing Lewis structures?
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1. Based on molecular formula, count the number of valence electrons.
2. Given the connectivity, connect the bonded atoms by a shared electron pair or a dash.
3. Count the number of electrons in the bonds and get the remainder.
4. Add remainder to the atoms to get 8 in valence shell.
5. Calculate the formal charge. - What is the formula to calculate formal charge?
- FC = Group # - (# unshared electrons - 1/2 # shared electrons)
- What are line structures?
- Structures with all C's and H's omitted.
- What are condensed structures?
- Structures which show all the structural units (e.g. CH3)
- What is VSEPR?
- Valence Shell Electron Pair Repuslion ... a method for determining molecular geometry.
- What are the important principles of VSEPR?
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1. Electron pairs in carbon always form at tetrahedral angles.
2. Molecular shape dependent upon the bonded atoms and NOT their unshared pairs. - What are the most important VSEPR shapes in organic chemistry?
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1. Tetrahedral
2. Pyramidal
3. Trigonal Planar
4. Bent - What is the trend in association between bond angles and unshared electron pair repulsion.
- 2 bonded pairs < 1 bonded pair + 1 unshared pair < 2 unshared pairs
- What are the two different types of stereoisomers?
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1. diastereoisomers
2. enantiomers - What are diastereoisomers?
- Non-mirror image stereoisomers.
- What are enantiomers?
- Mirror image stereoisomers.
- What is a Bronsted-Lowry acid?
- A substance that donates an H+.
- What is a Bronsted-Lowry base?
- A substance that accepts an H+.
- What is a Lewis acid?
- An electron pair acceptor.
- What is a Lewis base?
- An electron pair donator.
- What is the acid-dissociation constant?
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Ka = [H30+][A-]/[HA]
The equilibrium constant for the dissociation of an acid in water. - What is the pKa?
- - log Ka
- What is the relationship between Ka and acid strength?
- The larger the Ka the stronger the acid.
- What is the relationship between pKa and acid strength?
- The smaller the pKa the stronger the acid.
- What are the indicators of acid strength?
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1. H-A bond strength.
2. Electronegativity.
3. Electron delocalization in conjugate base. - What is the trend associated with the H-A bond strength?
- The weaker the H-A bond the stronger the acid.
- What is the trend associated with electronegativity?
- The more electronegative an H+ substrate the stronger an acid it is.
- Why does electron delocalization increase acidity?
- Affects the equilibrium of the reaction by stabilizing the conjugate base pulling equilibrium towards it.