Organic Chemistry II Flashcards
What are the prefixes for the first 12 alkanes?
Meth, eth, prop, but, pent, hex, hept, oct, non, dec, undec, dodec.
What are the 5 steps used to name alkanes according to IUPAC rules?
- Find the longest chain. 2. Number the chain so that the lowerst set of numbers is obtained for the substituents. 3. Name and alphabetize the substituents. 4. Assign a number to each substituent. 5. Complete the name.
In case of an “en-ol”, which carbon recieves the lowers number?
The carbon attached to the alcohol group is assigned the lowest number.
What is a diol?
A diol is a molecule with two hydroxyl (OH) groups.
T/F, an aldehyde has a carbonyl group somehwere in the middle of a carbon chain?
False, in an aldehyde, the carbonyl group is at the end of the carbon chain.
T/F, a ketone has the carbonyl group at one end of a carbon chain?
False, in a ketone, the carbonyl group is somehere in the middle of the carbon chain.
In the case of an “en-one”, which carbon recieves the lowest number?
The carbonyl carbon receives the lowers number.
What type of compound does a -COOH group deonote?
The COOH group denotes a carboxylic acid.
What is the common name for methonoic acid?
Methanoic acid = formic acid.
What is the common name for ethanoic acid?
ethanoic acid = acetic acid
What is the common name for propanoic acid?
Propanoic acid = propionic acid
Name RC≡N:
Nitrile / Cyanide
Name RSH
Thiol
Name R₂S
Sulfide.
Name RNO₂
Nitro.
Name RN₃
Azide.
Name RN₂+
Diazo.
Name the prefix and suffix for Carboxylic Acid?
Carboxy- / -oic acid
Name the prefix and suffix for Ester.
alkoxycarbonyl- / -oate
Name the prefix and suffix for Acyl Halide?
halocarbonyl- / -oyl halide
Name the prefix and suffix for Amide.
amido- / -amide
Name the prefix and suffix for Nitrile?
cyano- / -nitrile
Name the prefix and suffix for Aldehyde?
oxo- / -al
Name the prefix and suffix for Ketone?
oxo- / -one
Name the prefix and suffix for Alcohol?
hydroxy- / -ol
Name the prefix and suffix for Thiol?
sulfhydryl- / -thiol
Name the prefix and suffix for Amine?
amino- / -amine
Name the prefix and suffix for Ether?
alkoxy- / -ether
Name the prefix and suffix for Sulfide?
alkylthio- / -sulfide
Name the prefix and suffix for Nitro?
nitro- / ~
Name the prefix and suffix for Azide?
azido- / -azide
Name the prefix and suffix for Diazo?
diazo- / ~
What is a strctural isomer?
Structural isomers have the same chemical formulas, but different atomic connectivity.
What is a stereoisomer?
Stereoisomers are compounds that differ only in respect to the spatial arrangement of their atoms.
Order the following conformations of n-butane according to energy elvels (low to high): gauche, anti, eclipsed, totally eclipsed.
Anti, gauche, eclipsed, totally eclipsed.
What are the three cyclic hexane conformers?
Chair, boat, twisted boat.
Order the three cyclo hexane conformers according to energy levels?
Low to High: Chair, twisted boat, boat.
T/F, axial hydrogens are parallel to the ring?
False, axial hydrogens are perpendicular to the ring.
T/F, bulky groups prefer the equatorial position over the axial position?
True.
What are geometric isomers?
Geometric isomers are molecules that differ with respect to the spatial relationship of substituents around a double bond.
What is a chiral molecule?
A chiral molecule is a molecule that is not superimposable upon its mirror image.
What are enantiomers?
Enantiomers are chiral molecules that are non-superimposable mirror images of each other.
T/F, achiral moleules are optically active?
False, achiral molecules are optically inactive.
What is a dextrorotatory (+) compound?
A dextrorotatory compound rotates polarized light to the right (clockwise)
What is a levoratory (–) compound?
A levorotatory compound rotates polarized light to the left (counterclockwise).
What is a racemic micture?
A racemic mixture contains equal amounts of both enantiomers.
How many stereoisomers are possible for a molecule with four chiral centers?
2^n2^4 = 16
What are diastereomers?
Diastereomers are stereoisomers that are not mirror images of each other.
What types of molecules are optically active?
Chiral molecules are optically active.
What is a meso compound?
A meso compound is a molecule that possesses stereocenters but has a plane of symmetry. It is achiral and therefore optically inactive.
What type of chemical bond involves the sharing of electrons?
Covalent bonds involve the sharing of electrons.
What type of chemical bond involves the transfer of electrons?
Ionic bonds involve the transfer of electrons.
Which orbital has a spherical shape?
”s” orbitals are spherically shaped.
Which orbital has a bi-lobed shape?
“p” orbitals are bi-lobed.
T/F, all single bonds are sigma bonds?
True.
What type of bond results when two p orbitals overlap?
Two overlapping p orbitals form a pi bond.
What are the components of a double bond?
A double bond is composed of 1 sigma and 1 pi bond.
What are the components of a tripple bond?
A tripple bond is composed of 1 sigma and 2 pi bonds.
T/F, a pi bond can exist without a sigma bond?
False, a pi bond cannot exist independently of a sigma bond.
Which type of bond (pi or sigma) is stronger?
A sigma bond is generally stronger than a pi bond.
What is the hybridization of the carbon atom in CH4? What are the bond angles?
sp^3, 109.5º
What is the bond angle between sp hybridized atoms?
180º
What is the bond angle between sp^2 hybridized atoms?
120º
What is the general formula of a noncyclic alkane?
The general formula of an alkane is (Cn)(H2n)+2
How many other carbons are 1º, 2º, 3º and 4º carbons bonded to?
1, 2, 3, and 4 other carbons respectively.
How does increasing molecular weight affect the boiling point and melting point of an alkane?
Increased molecular weight results in increased boiling and melting points.
How does increased branching affect the boiling point of an alkane?
Increased branching lowers the boiling point.
What are the three steps of a halgenation reaction?
The three steps of halogenation are: initiation, propagation, and termination.
Which step of halogenation does the following reaction represent? X₂ ––hv or ∆––➜ 2X●
Initiation
Which step of halogenation does the following reaction represent? 2X● ––––➜ X₂
Termination.
Which step of halogenation does the following reaction represent? R● + X₂ ––––➜ RX + X●
Propagation.
Which step of halogenation does the following reaction represent? X● + R● ––––➜ XR
Termination.
Which step of halogenation does the following reaction represent? X● + RH ––––➜ HX + R●
Propagation.
Which step of halogenation does the following reaction represent? 2R● ––––➜ R₂
Termination.
What is the order of free radical stability?
3º > 2º > 1º> methyl.
What type of reaction involves breaking down large alkanes into smaller ones?
Pyrolysis or “cracking” uses heat to break down large alkanes into smaller ones.
What are the products of the complete combustion of an alkane?
The complete combustion of an alkane produces: CO2, H2O, and heat.
Is a nucleophile electron rich or elctron poor?
A nucleophile is electron rich.
All else being equal, how does basicity affect the strength of a nucleophile?
The stronger the base, the stronger the nucleophile.
How many steps are involved in an SN1 reaction? What are they?
There are two steps in an SN1 reaction:1st, the molecule dissociates into a carbocation and a leaving group.2nd, the nucleophile combines with the carbocation.
What is the order of carbocation stability?
3º > 2º > 1º > methyl.
Which step in an SN1 reaction is the rate determining step?
The first step, the formation of the carbocation, is the rate determining step.
T/F, the rate of an SN1 reaction is dependent on the concentration of the nucleophile?
False, the rate is only dependent on the concentration of the original molecule.
How can SN1 reaction rate be increased?
1, stabilize the carbocation by increasing substitution and using a highly polar solvent. 2, use a better leaving group (weak base).
How does basicity affect the nature of a leaving group?
The weaker the base, the better the leaving group.
How many steps are invovled in an SN2 reaction?
SN2 reactions have one step.
Is the rate of an SN2 reaction dependent on the concentration of the substrate, of the nucleophile, or both?
The SN2 reaction rate is dependent on the concentration of both the substrate and the nucleophile.