Study sets matching "ochem 3"

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Study sets matching "ochem 3"

27 terms
OChem 3
Z
E
Primary Carbon
Secondary Carbon
An alkene with the higher substituent groups on the same side…
An alkene with the higher substituent groups on opposite side…
A carbon with 2 R group and 2 H
A carbon with 2 R groups and 1 H
Z
An alkene with the higher substituent groups on the same side…
E
An alkene with the higher substituent groups on opposite side…
OCHEM 3
Hydrogenation
Reactions with water
Ester are one class of molecule that u…
Catalyst
Dehydration:... Remove water (OH+H),creates new bond... Hydrolysis…
When an Ester is treated with water in the presence of H+,a c…
A catalyst is a substance that speeds up a reaction without i…
Hydrogenation
Reactions with water
Dehydration:... Remove water (OH+H),creates new bond... Hydrolysis…
33 terms
OCHEM 3
Nucleophile
electrophile
strong nucleophiles
LDA
- Lewis Base... - electron pair donor... - negative charge, partial…
- Lewis Acid... - electron pair acceptor... - positive charge, part…
OH-... RO-... R2N-... R-NH2... CN-
strong base
Nucleophile
- Lewis Base... - electron pair donor... - negative charge, partial…
electrophile
- Lewis Acid... - electron pair acceptor... - positive charge, part…
ochem 3
Ammonium Salts... (Functional Group Pictu…
Ammonium Salts ... (Non-covalent Interact…
Ammonium Salts... (Reason for Boiling Poi…
Ammonium Salts... (Reason for Water Solub…
As salts, they are held together by ionic bonds, which are fa…
Salts make Ionic bonds which being real bonds are much strong…
Salt is composed of a cation (ammonium ion) and an anion, and…
Ammonium Salts... (Functional Group Pictu…
Ammonium Salts ... (Non-covalent Interact…
As salts, they are held together by ionic bonds, which are fa…
40 terms
ochem 3
curved arrows
first step for drawing curved arrows
structures with both - and +
structures with only C-H... carbohydrates
go from electron rich (-) to electron poor (+)... move electron…
expand structure to show all H bonds... note how many bonds bein…
1. draw arrow from atom with - charge to bond nearest to atom…
1. draw arrow from double bond to bond connected to atom with…
curved arrows
go from electron rich (-) to electron poor (+)... move electron…
first step for drawing curved arrows
expand structure to show all H bonds... note how many bonds bein…
36 terms
OChem Exam 3
Cleave Alkene (Ozonolysis)
Primary Alcohol -> Aldehyde
Mild Permanganate Oxidation of Alkynes…
Cleave Alkyne
1. O3 ... 2. (CH3)2S
Swern Oxidation
KMnO4 H2O pH=7
1. KMnO4 KOH, heat ... 2. H3O+
Cleave Alkene (Ozonolysis)
1. O3 ... 2. (CH3)2S
Primary Alcohol -> Aldehyde
Swern Oxidation
21 terms
ochem 3
-NH2
-NHR
-NR2
-OR
sb/sn
sb/sn
sb/sn
sb/sn
-NH2
sb/sn
-NHR
sb/sn
12 terms
OChem #3
Hydroboration-oxidation
X2 Addition to Alkene
Hydrogenation
Oxymercuration-Demercuration
syn
anti
syn
syn + anti
Hydroboration-oxidation
syn
X2 Addition to Alkene
anti
41 terms
Ochem 3
Heteroatoms
Functional Group
Hydrocarbons
Aliphatic Hydrocarbons
Atoms other than carbon or hydrogen
Structural features that determine a molecule's geometry, phy…
Compounds made up of only the elements carbon and hydrogen.
Alkanes, Alkenes, and Alkynes
Heteroatoms
Atoms other than carbon or hydrogen
Functional Group
Structural features that determine a molecule's geometry, phy…
OChem #3
NaOH
EtOH
CH3OH
NaCN
E2/SN2
E1/SN1
SN1/E1
SN2
NaOH
E2/SN2
EtOH
E1/SN1
ochem 3
hemi-acetal
NaBH4
lithium dialkylcuprate
Tollen's Reaction
geminal alkoxy-alcohol
demurcuration
forms ketone from acid halide
uses silver nitrate in aqueous ammonia
hemi-acetal
geminal alkoxy-alcohol
NaBH4
demurcuration
Ochem 3
Alkene
Reactive bond of Alkene
Bulky bases give
Hoffman product
Double bonds
The 1pi bond
Hoffman product
Less substituted due to attack on less crowded H
Alkene
Double bonds
Reactive bond of Alkene
The 1pi bond
OCHEM 3
Strong Activators
Moderate Activators
Weak Activators
Weak Deactivators
NH2... NHR... OH... OR
NH(C=O)R... O(C=O)R
R... Ar
F... Cl... Br... I
Strong Activators
NH2... NHR... OH... OR
Moderate Activators
NH(C=O)R... O(C=O)R
118 terms
OChem 3
What is an amine?
How do amines usually participate in r…
Properties of amines
Which makes stronger hydrogen bonds: a…
any organic compound that contains a basic nitrogen atom
-amines can act as either bases or nucleophiles... -primary or s…
-melting point and boiling point increase with molecular weig…
Alcohols bc oxygen is more electronegative, and thus, it crea…
What is an amine?
any organic compound that contains a basic nitrogen atom
How do amines usually participate in r…
-amines can act as either bases or nucleophiles... -primary or s…
17 terms
ochem3
"non-bases"
Moderate bases
Strong Bases
SN1
H2O, ROH, RCO2H R2S, RSH, R3P, Cl, Br, I
NH3, RCO2-, -CN, RS- N3-
-OH, -OR, -C =-C-R
first 3 non bases
"non-bases"
H2O, ROH, RCO2H R2S, RSH, R3P, Cl, Br, I
Moderate bases
NH3, RCO2-, -CN, RS- N3-
OCHEM #3
ylide
intermediate radicals must be ___ for…
define oxidation [O]
MnO2 selectively oxidizes
molecule with both + and - charge on adjacent atoms
symmetrical
lose H bond, gain C-O bond
allylic/benzylic OH's
ylide
molecule with both + and - charge on adjacent atoms
intermediate radicals must be ___ for…
symmetrical
20 terms
Ch. 3 ochem
constitutional isomers
primary carbon
secondary carbon
tertiary carbon
compounds that have the same molecular formula but the atoms…
carbon bonded to only one other carbon
carbon bonded to 2 other carbons
carbon bonded to 3 other carbons
constitutional isomers
compounds that have the same molecular formula but the atoms…
primary carbon
carbon bonded to only one other carbon
10 terms
ochem 3
hydohalogenation
acid-catalyzed hydration
halogenation
halohydrin formation
syn and anti
syn and anti
anti
anti
hydohalogenation
syn and anti
acid-catalyzed hydration
syn and anti
27 terms
ochem3
H2SO4, H2O/HgSO4
9BBN/H2O2, NaOH
CO2 and acid
2 acids
ketone reagents
aldehyde reagents
terminal alkane treated with O3/H2O
internal alkane treated with O3/H2O
H2SO4, H2O/HgSO4
ketone reagents
9BBN/H2O2, NaOH
aldehyde reagents
ochem 3
Absolute configuration
Achiral
Achirotopic
Anomers
A designation of the position or order of arrangement of the…
Not chiral. A necessary and sufficient criterion for achirali…
The opposite of chirotopic. See"chirotopic" below.
Diastereomers of glycosides or related cyclic forms of sugars…
Absolute configuration
A designation of the position or order of arrangement of the…
Achiral
Not chiral. A necessary and sufficient criterion for achirali…
33 terms
ochem3
ADME
Affinity
Analog
Combinatorial Synthesis
Absorbtion, Distribution, Metabolism, Excretion
Tendency of a molecule to associate with another
An analog is a drug whose structure is related to that of ano…
Synthesis starting with building blocks
ADME
Absorbtion, Distribution, Metabolism, Excretion
Affinity
Tendency of a molecule to associate with another
5 terms
OChem Ch.3
Name quantum numbers and meaning
Molecular orbitals
Bonds
Hybridization
n - energy level... l - subshell (s,p,d,f)... ml - orbital... ms - spin
Anti and bonding
Single - rotation... Double - no rotation... Triple - no rotation
Sp3, sp2, sp
Name quantum numbers and meaning
n - energy level... l - subshell (s,p,d,f)... ml - orbital... ms - spin
Molecular orbitals
Anti and bonding
OChem Quiz 3
1 C
2 C
3 C
4 C
meth
eth
pro
but
1 C
meth
2 C
eth
Ochem3
True or False? A simple distillation,…
True or False? A simple distillation,…
True or False? A simple distillation,…
True or False? A simple distillation,…
False
True
False
False
True or False? A simple distillation,…
False
True or False? A simple distillation,…
True
27 terms
Ochem exam 3
nucleophile
electrophile
(Functional groups)
aldehyde
(- charge)... an electron rich species that donates an electron…
(+ charge)... an "electron lover" or substance that accepts an e…
...
(RCHO)
nucleophile
(- charge)... an electron rich species that donates an electron…
electrophile
(+ charge)... an "electron lover" or substance that accepts an e…
ochem exam 3
HCl pKa
Sulphuric Acid H2SO4 pKa
Protonated alcohol/water pKa
Carboxylic acid pKa
-7
-5
-2
~4-5
HCl pKa
-7
Sulphuric Acid H2SO4 pKa
-5
55 terms
OCHEM EXAM 3
Cytosine
Pyrimidine
Thymine
nucleotides
What amino acid is this?
What class is cytosine classified as?
What amino acid is this?
What are the building blocks of RNA and DNA?
Cytosine
What amino acid is this?
Pyrimidine
What class is cytosine classified as?
58 terms
OChem Test 3
good, good
good, good
good
good
Br- is a ___ nucleophile and a ___ leaving group
I- is a ___ nucleophile and a ___ leaving group
CH3S- is a ___ nucleophile
RS- is a ___ nucleophile
good, good
Br- is a ___ nucleophile and a ___ leaving group
good, good
I- is a ___ nucleophile and a ___ leaving group
14 terms
Ochem Lab- EXP 3
caffeine structure
what techniques will be used?
what is difficult about this process?
what ar the major components of tea le…
solid-liquid, and lie-liq extractions and sublimation (purifi…
complicated by the fact that the natural source (plant, anima…
cellulose, proteins, pigments, and tannins
caffeine structure
what techniques will be used?
solid-liquid, and lie-liq extractions and sublimation (purifi…
Ochem 3
Reacciones de éteres
Éteres con sustituyentesprimarios y se…
Éteres con sustituyentes terciarios
Éteres con exceso del ácido
Los éteres se protonan y son atacados por un nucleófilo
Reaccionan con HBr o HI y por SN2. El oxigeno se protona y el…
Se protona el oxígeno y se forma el carbocatión. El nucleófil…
Forman dos halo alcanos y agua
Reacciones de éteres
Los éteres se protonan y son atacados por un nucleófilo
Éteres con sustituyentesprimarios y se…
Reaccionan con HBr o HI y por SN2. El oxigeno se protona y el…
16 terms
OCHEM Chapter 3- Bonding
Quantum numbers
Bonding orbitals
Antibonding orbitals
Single bonds
describe the size, shape, orientation, and number of atomic o…
created by head-to-head or tail-to-tail overlap of atomic orb…
created by head-to-head or tail-to-tail overlap of atomic orb…
-are sigma bonds... -contain two electrons
Quantum numbers
describe the size, shape, orientation, and number of atomic o…
Bonding orbitals
created by head-to-head or tail-to-tail overlap of atomic orb…
Ochem Ch. 3
Brønsted-Lowry acid and bases
Brønsted-Lowry acid
Brønsted-Lowry base
Conjugate base
based on the transfers of a proton (H+)
proton donor
proton acceptor
negative charge
Brønsted-Lowry acid and bases
based on the transfers of a proton (H+)
Brønsted-Lowry acid
proton donor
31 terms
OChem Ch 10.3
alkyl halide
PX3
H+, alkyl halide
alcohol
from alcohol to alkyl halide-no shift
from alcohol to alkyl halide-with shift
alkyl halide
PX3
from alcohol to alkyl halide-no shift
Chapter 1 &3 ochem
A pie bond makes a molecule a what?
A nucleophil is what? Has a what charge?
Electrophil is what?
Alkane(hydrocarbon)
Base and nucleophil
negative.. Seeking nucleus of other atoms; BASE
a positive charge
r-h example ch3 -ch3 linear
A pie bond makes a molecule a what?
Base and nucleophil
A nucleophil is what? Has a what charge?
negative.. Seeking nucleus of other atoms; BASE
16 terms
Ochem Ch 3
alkane... R-H. R could be a methyl, ethyl…
alkene... functional group=double bond (C…
alkyne... functional group=triple bond (C…
aromatic ring... functional group=phenyl
What is this structure?
What is this structure?
What is this structure?
what is this structure?
alkane... R-H. R could be a methyl, ethyl…
What is this structure?
alkene... functional group=double bond (C…
What is this structure?
55 terms
Ochem Ch 3
alkanes
hydrocarbons
straight-chain alkanes
constitutional isomers
composed of only carbon atoms and hydrogen atoms and contain…
compounds that contain only carbon and hydrogen; alkanes are…
alkanes in which the carbons form a continuous chain with no…
compounds such as butane and isobutane that have the same mol…
alkanes
composed of only carbon atoms and hydrogen atoms and contain…
hydrocarbons
compounds that contain only carbon and hydrogen; alkanes are…
63 terms
Chads OChem 3, 4
alkene is the
where does the hydrogen go in {alkene…
explain markovnikov
nucleophile goes to the more
nucleophile in an alkene reaction
to the less substituted side to form the more substituted sta…
alkene attack the less substituited side in order to get more…
substituted side where the electrophile is
alkene is the
nucleophile in an alkene reaction
where does the hydrogen go in {alkene…
to the less substituted side to form the more substituted sta…
Ochem Test 3
chiral center
enantimor
racemic mixture
enantipure
tetrahedral carbon with 4 different substiuents
non-superimposed mirror image of a chiral center, the only di…
50:50 mixture of an enantimor
100% mixture of one enantimor
chiral center
tetrahedral carbon with 4 different substiuents
enantimor
non-superimposed mirror image of a chiral center, the only di…
Ochem Final-chapt. 3
Gauche conformer
Anti conformer
Alkyl halide
Ketone
Methyls close to eachother
Methyls on opposite eachother
Gauche conformer
Methyls close to eachother
Anti conformer
Methyls on opposite eachother
54 terms
Ochem exam 3
Increase electronegativity
Increase size of molecule
Bigger atom/ more polarizeable
Protic solvent
Decrease nucleophilicity
Decrease nucleophilicity
Increase nucleophilicity
Decrease nucleophilicity
Increase electronegativity
Decrease nucleophilicity
Increase size of molecule
Decrease nucleophilicity
Ochem 3-4
Nucleophilicity
Electrophilicity
Leaving group tendency
Sn1 mechanism
the more negative, the better the nucleophile... -deprotonate to…
the more positive, the better the electrophile... -protonate to…
the weaker the base, the better the leaving group
-carbocation intermediate, 2 step... - 3° > 2° > 1° > CH₃... -polar…
Nucleophilicity
the more negative, the better the nucleophile... -deprotonate to…
Electrophilicity
the more positive, the better the electrophile... -protonate to…
39 terms
Ochem exam 3
-Cyclic... -conjugated (resonance)... -Flat…
Molecules that bond with a Hydrogen co…
O-H molecules
The more electronegative = The more so…
Aromatic compounds are:
What molecules can H-bond with water ?
What molecules can H-bond with water and itself?
How do you determine which molecule is most soluble in water?
-Cyclic... -conjugated (resonance)... -Flat…
Aromatic compounds are:
Molecules that bond with a Hydrogen co…
What molecules can H-bond with water ?
41 terms
OChem Ch. 2 & 3
Stability of Conjugate Bases
Element Effects
Inductive Effects
Resonance Effects
I. Element Effects... II. Inductive Effects... III. Resonance Effec…
Acidity of HA increases as the electronegativity of A- increa…
Acidity of HA increases when we put electronegative atoms nea…
Delocalization of charage through resonance
Stability of Conjugate Bases
I. Element Effects... II. Inductive Effects... III. Resonance Effec…
Element Effects
Acidity of HA increases as the electronegativity of A- increa…
ochem exam 3
synthesis of alcohols from haloalkanes…
synthesis of alcohols by reductions of…
oxidation of primary alcohol to carbox…
oxidation of primary alcohol to aldehyde
use OH-, H2O for SN2 (after chlorination)... use H2O for SN1 (af…
LiAlH4 = strong H- equivalent (powerful reducing agent)... NaBH4…
Na2Cr2O7 (w/ H2SO4, H2O)... ex) CH3CH2OH → CH3COOH
PCC (w/ CH2Cl2)... - H2 from formula?... ex) CH2CH2OH → CH2COH
synthesis of alcohols from haloalkanes…
use OH-, H2O for SN2 (after chlorination)... use H2O for SN1 (af…
synthesis of alcohols by reductions of…
LiAlH4 = strong H- equivalent (powerful reducing agent)... NaBH4…
ochem test 3
LiAlH4 and NaBH4
Wolff-kishner (NH2NH2,NaOH)
H30 and Heat to a Ctriple bond to N
KmNo4
reduction turns o= to oh- and h-
Reduction from o= to two hydrogens
Carboxylic acid
create a carboxylic acid
LiAlH4 and NaBH4
reduction turns o= to oh- and h-
Wolff-kishner (NH2NH2,NaOH)
Reduction from o= to two hydrogens
OChem lecture 3
What is an orbital?
AB2
AB3
AB4
Probability of finding an electron
SP, 180, linear, free rotation
SP2, 120, trigonal planar
SP3, 109, tetrahedral
What is an orbital?
Probability of finding an electron
AB2
SP, 180, linear, free rotation
29 terms
Ochem Exam 3
3 prime alkyl halides with strong base
3 prime alkyl halides with weak base/n…
1 prime alkyl halide with strong nucle…
1 prime alkyl halide with strong steri…
E2 mechanism
mix of SN1 and E1
SN2 mechanism
E2 mechanism
3 prime alkyl halides with strong base
E2 mechanism
3 prime alkyl halides with weak base/n…
mix of SN1 and E1
13 terms
OCHEM Chapter 3
principal quantum number
azimuthal quantum number
magnetic quantum number
spin quantum number
First quantum number, designated as the letter "n." It takes…
Second quantum number, designated by the letter "l." This "an…
The third quantum number, designated by m_l, it describes a p…
The quantum number that has only two possible values, +1/2 an…
principal quantum number
First quantum number, designated as the letter "n." It takes…
azimuthal quantum number
Second quantum number, designated by the letter "l." This "an…
OCHEM test 3
H2SO4, H2O, HEAT
PBr3
HX ... (HI, HCl, HBr, HF)
SOCl2
E1 like
2/3 alcohol=Sn1 like... CH3/1 alcohol=Sn2 like... Sub one Br
Sn1 like... Sub one X
Sn2 like... Sub one Cl
H2SO4, H2O, HEAT
E1 like
PBr3
2/3 alcohol=Sn1 like... CH3/1 alcohol=Sn2 like... Sub one Br
46 terms
Ochem Ch 3
functional group
pi bond
nucleophile
ethane
atom or group of atoms with characteristic chemical and physi…
common in c-c and c-o double bonds; easily broken in chem rea…
a chemical species that donates an electron pair to an electr…
CH3CH3; only sigma bonds, no functional group; no polar bonds…
functional group
atom or group of atoms with characteristic chemical and physi…
pi bond
common in c-c and c-o double bonds; easily broken in chem rea…
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