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MCAT Organic Chemistry
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Subjects
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mcat
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science
Instructions:
Answer 50 questions in 15 minutes.
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Match each statement with the correct term.
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1. Cleaves double bond in half - it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
angle strain
markovnikov's rule
Alkane nomenclature
ozonolysis
2. Carbon with four different substituents and lack a plane of symmetry
alcohol
quantum numbers
chiral center
vicinal
3. Carbonyl located at the end of the chain named by replacing al with e. e.g. butanal
alkyne
sp
conformational isomer
aldehyde
4. When boat flips
Haloalkane
chiral center
diastereomers
ring flip
5. When two atomic orbitals combine. obtained mathematically by adding or subtracting wave functions. if sings are the same - make bonding - if different - less stable antibonding.
alkyne
racemic mixture
molecular orbital
oxidizing
6. O3
electrophilic addition of X2
ozonolysis
sp3
nucleophile
7. Is bonded to only one other carbon atom
primary carbon
catalytic hydrogenation
sp2
hot - acidic potassium permanganate
8. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
peroxycarboxylic acid
geminal
triple bond
2^n
9. Reducing an alkene by adding molecular hydrogen to double bond with aid of metal catalyst. e.g. pt - pd - ni. takes place on surface of metal so it does syn addition
Vinyl
potassium permanganate
peroxycarboxylic acid
catalytic hydrogenation
10. Common name for ethyne
fischer projection
isomer
Ignored
Acetylene
11. Nucleus lover. electron rich species that are attracked to charged atoms
isomer
hot - acidic potassium permanganate
formaldehyde
nucleophile
12. A molecule with an internal plane of symmetry
reducing
electrophile
Combustion
meso compound
13. Compounds with halogen
Haloalkane
acetaldehyde
hybridization
angle strain
14. A = observed rotation / concentration * length
absolute configuration
Vinyl
allyl
specific rotation
15. Functionality is specified by alkoxy- prefix. ROR
ozonolysis
ethers
geometric isomers
2^n
16. What is produced when o3 with lialh4 or nabh4
alcohol
electrophilic addition of X2
ozonolysis
basicity
17. E of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
chiral center
vicinal
electrophilic addition of HX
carboxylic acid
18. One s and three p orbitals
sp3
peroxycarboxylic acid
Alkyne
cold potassium permanganate
19. If reagent has a bunch of oxygen
covalent bond
chiral center
sp3
oxidation
20. Nonsuperimposable mirror image of chiral objects - a specific steroisomer.
Haloalkane
enantiomer
catalytic hydrogenation
protic solvent
21. Object that is not superimposable upon mirror image
angle strain
chiral
markovnikov's rule
polymerization
22. Three different substitutents often have plane of symmetry. and rotation of 180 will allow molecule to be superimposed on mirror image
aldehyde
achiral
racemic mixture
allyl
23. Non mirror image of configurational isomers. cis and trans alkenes are them. possible when a molecule has two or more stereogenic centers that differ at some but not alll of the centers. they require multiple chiral centers.
chiral
Alkyne
relative configuration
diastereomers
24. Same molecular formula but different structure
specific rotation
cold potassium permanganate
electrophilic addition of free radicals
isomer
25. When a molecular orbital is formed head to head or tail to tail. all single bonds are tehese.
aprotic solvent
sigma bond
sp3
achiral
26. No double bonds. it has the maximum number of hydrogens.
diol
absolute configuration
saturated hydrocarbon
cold potassium permanganate
27. Results when cyclic molecules must assume conformations that have eclipsed interactions
torsional strain
nucleophile
reducing
configuration
28. Reaction of alkane with oxygen to form carbon dioxide - water and heat.
Haloalkane
Alkyne
Combustion
weak bases
29. Iso - neo - cyclo
triple bond
not ignored
geminal
electrophilic addition of HX
30. Diols with hydroxyl group on adjacent carbon
vicinal
lindlar's catalyst
conformational isomer
nucleophile
31. Share molecular formula but have different chemical and physical properties
structural isomers
acetaldehyde
geminal
pi bond
32. Alphabetical order of alkane rxn
disproportionation
alcohol
weak bases
combustion - disproportionation - free - radical substitution - pyrolysis
33. Transfer of electrions from one atome to another
protic solvent
Combustion
ionic bond
nucleophile
34. Zn/h or CH3/s with ozonolysis
propionaldehyde
reducing
Alkene
oxidizing
35. Alkenes oxidzed with kmno4 - if made with cold - dilue - make OH on each side of double bond - diols or glycol in syn orientation
halogen
cold potassium permanganate
stereoisomers
lindlar's catalyst
36. Carbon carbon triple bonds. Suffix-yne.
not ignored
electrophilic addition of free radicals
propionaldehyde
Alkyne
37. Rotations cancel each other out therefore no optical activity
potassium permanganate
geminal
racemic mixture
angle strain
38. Always receive number one. contain carbonyl and OH group - very oxidized. highest priority functional group.
ionic bond
formaldehyde
enantiomer
carboxylic acid
39. Monosubstituted ethylene
torsional strain
Vinyl
saturated hydrocarbon
diol
40. How many stereoisomers can a molecule have with n chiral centers
quantum numbers
electrophilic addition of H2O
Haloalkane
2^n
41. Propylenes attached to a backbone at the C-3 position. Meaning the double bond at end of the chain and single bonded carbon at rest
allyl
Alkane nomenclature
gauche conformation
electrophilic addition of HX
42. Nonterminal alkenes are cleaved to form two molar equivalent of carvoxylic acid ..make keton
propionaldehyde
diol
basicity
hot - acidic potassium permanganate
43. One s and two p 120 degree apart
fischer projection
sigma bond
electrophilic addition
sp2
44. Goal is to produce most stable carbocation
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45. Not solvated
aprotic solvent
torsional strain
potassium permanganate
chiral center
46. A sigma bond and two pi bonds
triple bond
oxidizing
racemic mixture
anti conformation
47. Diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov - alcohol produced
electrophile
halogen
oxidation
hydroboration
48. Solvents with protons in solution - e.g. water or alcohol. large atoms tend to be better nucleophiles in here because they can shed the solvating protons around them and are more polarizable
angle strain
carbonyl
protic solvent
aldehyde
49. When two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
combustion - disproportionation - free - radical substitution - pyrolysis
oxidation
pi bond
formaldehyde
50. Carbonyl located in middle or somewhere in chane. Named with One
specific rotation
ketone
pi bond
diastereomers
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