ORGANIC 1: Chapter 1: Hybridization & Bonding Flashcards
What is the hybridization of the indicated atom?
sp2
What is the hybridization of the indicated atom?
sp3
What is the hybridization of the indicated atom?
sp
What is the hybridization of the indicated atom?
sp
What is the hybridization of the indicated atom?
sp3
What is the hybridization of the indicated atom?
sp3
True or False
The indicated atom is sp3 hybridized.
False!
Because this atom with a lone pair is adjacent to a pi bond, it can participate in resonance, which affects the hybridization. This atom has a hybridization in between sp2 and sp3.
Look out for allylic lone pairs! (allylic = adjacent to a double bond)
What is the hybridization of the indicated atom?
sp3
What is the hybridization of the indicated atom?
sp2
What is the hybridization of the indicated atom?
sp3
What is the relationship between bond length & bond strength?
The shorter the bond, the stronger it is and
the longer the bond, the weaker it is
Which of the indicated bonds in the molecule shown below is the longest?
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A
Which of the indicated bonds in the molecule shown below is the shortest?
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C
Which of the indicated bonds in the molecule shown below is the strongest?
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C
Which of the indicated bonds in the molecule shown below is the weakest?
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A
Sigma bonds are formed from the overlap of _______ orbitals.
Hybrid orbitals (sp, sp2, sp3, etc.) or atomic orbitals (hydrogen-hydrogen/carbon-hydrogen)
Pi bonds are formed from the overlap of _______ orbitals.
P orbitals
What type of bonding is depicted below?
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Sigma bonding
What type of bonding is depectied below?
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Sigma anti-bonding
What type of bonding is depectied below?
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Pi bonding
What type of bonding is depectied below?
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Pi anti-bonding
What is the formula to calculate formal charge?
Formal Charge = # valence electrons - # bonds - # electrons
or
Formal Charge = # valence electrons - # lines - # dots
What is the formal charge of the indicated atom?
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0
What is the formal charge of the indicated atom?
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+1
What is the formal charge of the indicated atom?
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+1
What is the formal charge of the indicated atom?
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+1
What is the formal charge of the indicated atom?
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-1
Define
Constitutional Isomers
Molecules that have the same molecular formula but different connectivity
How many valence electrons does oxygen have?
6
How many valence electrons does nitrogen have?
5
How many valence electrons does carbon have?
4
Define
Condensed Structure
Structural representation that omits some/all covalent bonds and displays all atoms bound to a carbon in the list next to it.
(i.e. CH3CH3)
Bond Angle & Geometry
sp2
120°, trigonal planar
Bond Angle & Geometry
sp3
109.5°, tetrahedral
Bond Angle & Geometry
sp
180°, linear
What hybridization does an atom have if it has 3 regions of electron density?
sp2
What hybridization does an atom have if it has 4 regions of electron density?
sp3
What hybridization does an atom have if it has 2 regions of electron density?
sp
How many atoms in the molecule below display tetrahedral geometry?
6 atoms (all sp3 hybridized atoms)
What molecular geometry does the indicated atom display?
Trigonal planar (sp2 hybridized)
What type of bonding is depicted below?
Sigma bonding
What type of bonding is depicted below?
Sigma anti-bonding
What orbitals overlap to form the C-C bond in ethane (CH3CH3)?
sp3-sp3
What orbitals overlap to form the C-H bond in ethane (CH3CH3)?
sp3-s
What orbitals overlap to form the C-C bonds in ethene (CH2=CH2)?
Sigma: sp2-sp2
Pi: p-p
What orbitals overlap to form the C-H bond in ethene (CH2=CH2)?
sp2-s
What orbitals overlap to form the C-C bond in ethyne (CH≡CH)?
Sigma: sp-sp
Pi: p-p x2
What orbitals overlap to form the C-H bond in ethyne (CH≡CH)?
sp-s
What is the hybridization of the indicated atom?
sp
How many hydrogens are present on the indicated atom?
0 hydrogens
What orbital does the lone pair on the carbon occupy?
sp
How many hydrogens are present on the indicated atom?
1 hydrogen
How many hydrogens are present on the indicated atom?
3 hydrogens
What is the formal charge of the indicated atom?
+1
What is the formal charge of the indicated atom?
+1
What is the formal charge of the indicated atom?
0
Given the formal charge of the indicated atom, how many lone pairs are present?
Two lone pairs (4 total electrons)
Given the formal charge of the indicated atom, how many lone pairs are present?
Three lone pairs (6 total electrons)
Given the formal charge of the indicated atom, how many lone pairs are present?
One lone pair (2 total electrons)
Given the formal charge of the indicated atom, how many lone pairs are present?
Two lone pairs (4 total electrons)
Given the formal charge of the indicated atom, how many lone pairs are present?
One lone pair (2 total electrons)
Given the formal charge of the indicated atom, how many lone pairs are present?
Two lone pairs (4 total electrons)
How many sp3 carbons are present in the molecule below?
Two
How many sp2 carbons are present in the molecule below?
Five
What orbitals overlap to form the C-H bond in methane (CH4)?
sp3-s
What orbital are the lone pairs on the blue atom found in?
sp3 orbitals
What orbital are the lone pairs on the blue atom found in?
sp2 orbitals
*they are not in the p-orbital because that is where the pi bond occupies
What orbital is the lone pair on the blue atom found in?
The p orbital
*even though the atom appears to be sp3 hybridized, notice that it can resonate with the adjacent double bond. If a lone pair can resonate, it must be in the p orbital.
What orbital is the lone pair on the blue atom found in?
sp orbital
What orbital is the lone pair on the blue atom found in?
sp3 orbital
What orbital is the lone pair on the blue atom found in?
p orbital
Which compound is more polar?
B
The dipoles present in A cancel out.
Define
Methylene Group
A methylene group is a CH2 group found within long carbon chains.
What is the approximate bond angle of the C1-C2-C3 bond?
109.5°
due to the central atom being sp3 hybridized.
What is the approximate bond angle of the O4-C5-C6 bond?
120°
due to the central atom being sp2 hybridized.
Which atoms are connected via the strongest bond?
C5-O7
How many hydrogen atoms are present in the molecule below?
10 hydrogens
True or False
Resonance increases the stability of a molecule.
True!
Which of the following compounds has the longest bond?
D
This is due to the large atomic radius of iodine relative to the other halogens.