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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. Same chemical formula. same atomic connectivity . different in how atoms are arranged in space
reducing
stereoisomers
markovnikov's rule
electrophilic addition of X2
2. 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
alkyne
nonbonded strain
protic solvent
potassium permanganate
3. 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
catalytic hydrogenation
geminal
initiation propagation termination
ketone
4. Formed by mixing different types of orbitals
hydroboration
markovnikov's rule
lindlar's catalyst
hybridization
5. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
peroxycarboxylic acid
fischer projection
diol
hybridization
6. Functionality is specified by alkoxy- prefix. ROR
fischer projection
specific rotation
peroxycarboxylic acid
ethers
7. When boat flips
optical activity
ionic bond
acetaldehyde
ring flip
8. If reagent has a bunch of oxygen
oxidation
diastereomers
conformational isomer
stereoisomers
9. Lowest priority group projects into the page
Acetylene
relative configuration
ring flip
fischer projection
10. When bond angles deviate from ideal values
nonbonded strain
quantum numbers
Ignored
angle strain
11. One s and two p 120 degree apart
protic solvent
cold potassium permanganate
stereoisomers
sp2
12. A = observed rotation / concentration * length
fischer projection
acetaldehyde
specific rotation
mcpba
13. Goal is to produce most stable carbocation
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14. Use the Greek root for the number of carbons followed by the ending - - ane
reducing
Alkene
Alkane nomenclature
aldehyde
15. Cleaves double bond in half - it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
anti conformation
cold potassium permanganate
carboxylic acid
ozonolysis
16. Reaction of alkane with oxygen to form carbon dioxide - water and heat.
potassium permanganate
Combustion
electrophile
hot - acidic potassium permanganate
17. Methyl are 60 degrees apart. kinda stable
gauche conformation
Combustion
Acetylene
not ignored
18. Object that is not superimposable upon mirror image
Ignored
chiral center
ozonolysis
chiral
19. Nonsuperimposable mirror image of chiral objects - a specific steroisomer.
enantiomer
acetaldehyde
Vinyl
ionic bond
20. Results when nonadjacent atoms or groups compete for space. dominant source of energy in flagpole interactions of the boat conformation. thus it goes in various conformations like chair boat and twist.
alcohol
meso compound
ozonolysis
nonbonded strain
21. Rotations cancel each other out therefore no optical activity
torsional strain
racemic mixture
formaldehyde
Alkane nomenclature
22. Carbon carbon triple bonds. Suffix-yne.
sp2
stereoisomers
saturated hydrocarbon
Alkyne
23. What is produced when o3 with lialh4 or nabh4
potassium permanganate
optical activity
sp
alcohol
24. One s and three p orbitals
sp3
weak bases
covalent bond
allyl
25. In which one or morehydrogen atoms are replaced with a halogen atom. via free radical substitution
Acetylene
geometric isomers
2^n
halogenation
26. In presence of peroxide - oxygen or ultraviolet light. antimarkonikov because they want a stable free radical. therefore X ends up on least subsituted carbon
optical activity
formaldehyde
electrophilic addition of free radicals
mcpba
27. Nitrogen containing compound - longest chain attached to nitrogen used in backbone. use e and replace with AMINE. if more complex molecule present - use prefix amino. IF additional group added - use N-
amines
ring flip
specific rotation
polymerization
28. Is bonded to only one other carbon atom
primary carbon
meso compound
alkyne
stereoisomers
29. Chain of carbons connected by single bonds with hydrogen atoms attached.
Alkane
sp
eclipsed conformation
ring strain
30. Water can be added to alkenes under acidic conditions. make carbocation. ends with alcohol
electrophilic addition of H2O
mcpba
configuration
geometric isomers
31. Describes the exact spatial arrangement of groups of atoms independent of other molecules.
absolute configuration
reducing
diol
enantiomer
32. Results when cyclic molecules must assume conformations that have eclipsed interactions
torsional strain
molecular orbital
markovnikov's rule
nonbonded strain
33. Most similar. same molecule only at different points in their rotation. show them with newmans projections
propionaldehyde
torsional strain
conformational isomer
electrophilic addition of HX
34. Carbonyl located at the end of the chain named by replacing al with e. e.g. butanal
Combustion
aprotic solvent
aldehyde
carboxylic acid
35. When a molecular orbital is formed head to head or tail to tail. all single bonds are tehese.
disproportionation
Alkane
sigma bond
mcpba
36. E of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
quantum numbers
electrophilic addition of HX
gauche conformation
torsional strain
37. A sigma bond and two pi bonds
triple bond
structural isomers
enantiomer
Alkane nomenclature
38. Occur when a molecule is broken down by heat. used to reduce the avverage molecular weight of heavy oils. c - c - bonds are cleave dand make small chain alkyl radicals that recombine to form different alkanes
halogen
pyrolysis
diastereomers
Alkane nomenclature
39. Carbon with four different substituents and lack a plane of symmetry
alcohol
chiral center
diastereomers
acetaldehyde
40. Kmno4
aprotic solvent
ketone
potassium permanganate
hybridization
41. Diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov - alcohol produced
hydroboration
allyl
sigma bond
ring strain
42. F - CL - Br - I
vicinal
pi bond
halogen
electrophilic addition of X2
43. Zn/h or CH3/s with ozonolysis
gauche conformation
reducing
achiral
electrophile
44. O3
ozonolysis
hot - acidic potassium permanganate
aprotic solvent
triple bond
45. A radical transfers a hydrogen atom to another radical and makes an alkane and alkene
ionic bond
Alkane
disproportionation
torsional strain
46. Name for ethanal
nonbonded strain
weak bases
acetaldehyde
Haloalkane
47. Arise from angle strain - torsional strian and nonbonded strain
absolute configuration
Combustion
electrophilic addition of HX
ring strain
48. Steps of free radical substitution
electrophilic addition of X2
initiation propagation termination
catalytic hydrogenation
sigma bond
49. Name for mathanal
fischer projection
formaldehyde
protic solvent
eclipsed conformation
50. Electrons of pi bond are reactive and easily attacked by molecules that want e pair e.g. electrophiles.
electrophilic addition
C3H8 + 5O2 = 3CO2 + 4H2O + heat
molecular orbital
nucleophile
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