• Shuffle
    Toggle On
    Toggle Off
  • Alphabetize
    Toggle On
    Toggle Off
  • Front First
    Toggle On
    Toggle Off
  • Both Sides
    Toggle On
    Toggle Off
  • Read
    Toggle On
    Toggle Off

Card Range To Study



Play button


Play button




Click to flip

Use LEFT and RIGHT arrow keys to navigate between flashcards;

Use UP and DOWN arrow keys to flip the card;

H to show hint;

A reads text to speech;

106 Cards in this Set

  • Front
  • Back
Stereoisomers that are non superimposable mirror images
Stereoisomers that are NOT mirror images of each other
How many different groups are needed for a central Carbon atom to be considered Chiral?
How is a Chiral and Achiral central carbon different?
A Chiral has 4 different moleclules attached to the central C while the Achiral central C has a plain of semitry
How many chiral carbons are needed on a molecule to make the molecule chiral?
Just one
Define Optical Activity
It is that organic molecules rotate plane polarized light.
Enantiomers have atleast 2 forms.
1 rotates light (-) _____ ______
2 rotates light (+)_____ ______
(-) left - Levorotatory
(+) right - Dextrotatory
Do Achiral molecules rotate light?
Do Chiral molecules rotate light?
Who discovered Enantiomers?
Louis Pasteur
In IUPAC naming,
R =?
S =?
Counter clockwise
In IUPAC naming you take the lowest priority attached atom to the central C and point it?
Away from you
If you have a molecule with one chiral center it will have?
enantiomers (mirror images)
If you have a molecule with more than one chiral center you will have?
A possiblity of diastereomers (non mirror images)
The Threonine isomer that is naturally occuring and is an amino acid for our bodies is the ____isomer
Three things needed to be chiral?
Central C atome with 4 different attached molecules
No plane of Semitry
2R,3R -->2R,3S =
2S,3S --> 2R,3S =
2R,3R --> 2S,3S =
2R,3S --> 2S,3R =
You can tell if the molecule has a MESO form if it has _____?
A plane of symetry.
If the molecule is MESO does it have Optical activity?
If the molecule is MESO is it chiral?
No, its the same molecule?
What is a Racemic Mixture?
A mixture of 50:50 R,S enantiomers
How do you prepare a Alkyl Halide?
you make them from alcohols
When making Alkyl Halides, which has best reactivity: tertiary, secondary, primary, or methyl.
tertiary, Because SN1 rxn happens under neutral or acidic conditions and favors tertiary (Fast for SN1)
Primary and secondary alcohols work best with what molecules?
PBr3 and SOCl2
When making Alkyl Halides from tertiary alcohols, what should you use?
What is a Grignard Reaction?
They are a carbon metal bond.
R-Mg-X = a magnesium halide
What do they mean when they say an organometallic compound?
It means the metal is in the middle.
In Gringnard Reactions, what halide can NOT be used?
In Gringnard Reactions, what halides can be used?
Cl, Br, and I
In nucleophilic Substitutions Reactions, Alkyl Halides are generally electrophiles or nucleophiles?
If the Alkyl Halides are electrophilic, they either do 1 of 2 things, what are they?
1. substitution of X
2. elimination of HX (which equals an alkene so done't forget the double bond)
In substitution, the X is _______ by the OH-?
Replaced, X is the leaving group and leaves a + charge that the OH- take.
In elimination, the X is ________ by the OH-?
eliminated, the X leaves and the OH- takes an H, makes H2O and the alkene is formed.
Nucleophilis Substitution Rxn occurs by 2 pathway:
1. SN1
2. SN2
In SN reactions a nucleophile (Nu:-) reacts w/ a __________ and substitutes for a leaving group.
substrate (R-X), the X is replaces into (R-Nu)
In SN rxns, when Nu: is (-) the product is?
In SN rxns, when Nu: has no charge the product is?
When MAKING an alkyl halide:
1. Tertiary alcohols use what chemical for transformation?
2. Secondary & Primary use what chemical for transformation?
1. H-X
2. SOCl2 or PBr3
The SN2 reaction takes place in how many steps?
One step w/o an intermediate
In an SN2 reaction the NU: attacks where?
the back 180 from the X or LG
SN2 reactions the rate is determined by?
The concentration of the substrate (alkyl haildie) and the nucleophile
In an SN2 rxn, when the NU: attacks from the back it changes the molecules?
From an S to an R or vice versa
Common LG for an SN2 rxn are?
I-, Br-, Cl-
SN1 Reactions take place in what type of C substrate?
SN1 Reactions work in what type of environment?
Neutral or acidic
in an SN1 reaction is there an intermediate?
How many steps in an SN1 reaction
2 steps
In an SN1 reaction how does the leaving group leave?
In an SN2 reaction how does the leaving group leave?
as the Nu attacks the substrate, the LG group gets pushed off. This happens all at the same time that is why there is no intermediate.
The rate of an SN1 reaction depends on the?
Concentration of the substrate only
in an SN1 reaction, the Nu: can attack from where? and what does this make?
either side, because the LG is gone.
a racemic mixture 50:50
What are the LG groups in an SN1 reaction?
Same as SN2, Cl-, I-, Br-
Elimination reactions almost always give mixtures of _______ products.
Alexander Zaitsev's Rule?
The more highly substituated will be more prevelent in solution.
E1, the C-X bond?
How many steps?
Spontaniously breaks like in the SN1 (C is partially +)
2 steps (there is an intermediate)
E2, the C-X bond is?
How many steps?
based induced for bond cleavage like the SN2 (C is partially -)
1 step (no intermediate)
E1cB, the C-X bond is?
How many steps?
Base abstraction of the proton occurs 1st.
2 steps (there is an intermediate)
Don't forget, all E reactions give rise to ______?
double bonds.
Primary alkyl halide substitution use?
Primary alkyl halide eilmination (w/ OH) use?
If 2 carbons away from the carbonyl group use?
Secondary alkyl halide substitution use?
Terteriary alkyl halide:
Basic use?
Neutral use?
Acidic use?
Basic 2 away use?
SN1 (substitution) E1 (elimination)
Synthesis of an alcohol from a carbonyl cmpd is done by oxidation or reduction?
Synthesis of Alcohols:
Reduction of Aldehydes (R-C=O) gives __________ and uses ______ to do it.
Primary alcohols
Synthesis of Alcohols:
Reduction of Ketones (R-C-R, C=O) gives__________ and uses ______ to do it.
Secondary alcohols.
Synthesis of Alcohols:
Reduction of Carboxylic Acid (R-C-OH, C is =O) gives __________ and uses ______ to do it.
primary alcohols
Synthesis of Alcohols:
Reduction of Esters (R-C-OR, C=O) gives __________ and uses ______ to do it.
primary alcohols
Synthesis of Alcohols:
Formaldehyde (H2C=O) w/ a Gringnard (RMgX) gives what type of alcohol?
Synthesis of Alcohols:
Aldehydes (RC=O) w/ a Gringnard (RMgX) gives what type of alcohol?
Synthesis of Alcohols:
Ketones (RC=O,C) w/ a Gringnard (RMgX) gives what type of alcohol?
Synthesis of Alcohols:
In reduction of a carboxylic acid or ester, you add what?
LiAlH4 - 2 H's, one in the OH (comes from [H] and one because we got rid of the double bond from H3O+.
Synthesis of Alcohols:
in the gringnard reagent what part is the LG?
MgX, the R stays and attaches to the new molecule.
Reactions of Alcohols:
The dehydration of Alcohols is the?
elimination of H2O to give an alkene.
Reactions of Alcohols:
In Dehydration of OH, the H adds to what in the first step?
it adds to the OH making H2O
Reactions of Alcohols:
In Dehydration of OH, the second step H2O?
is the LG and removes it's self leaving a positive charge behind
Reactions of Alcohols:
In Dehydration of OH, the third step the the H2O?
Takes an H from the molecule.
Reactions of Alcohols:
In Dehydration of OH, the forth step, the H is now missing and what forms?
a double bond.
Reactions of Alcohols:
Oxidation of alcohols are the turning of what to what?
Alcohols to carbonyl compds.
Reactions of Alcohols:
Oxidation: Primary alcohols turn into?
Carboxylic acid
Reactions of Alcohols:
Oxidation: Secondary alcohols turn into?
Reactions of Alcohols:
Oxidation: Tertiary alcohols turn into?
No Rxn
Reactions of Alcohols:
What are the 3 Oxidation reagents?
Periodinane (expensive)
Reactions of Alcohols:
Conversion into Ethers steps
1. add Alkali metal or strong base NaH
2. add alkyl halide (Williamson ether synthesis)
Reactions of Alcohols:
Ethers: The best reactivity comes from what type of alkyl halides?
Primary, the more hindered the substrates the more E2 will occur.
Reactions of Alcohols:
Ethers: the CH3 that comes from the CH3-X is bonded to?
The O.
Reactions of Ethers:
can only under go one general reaction, what is it?
CLEAVED by a strong acid. HI or HBr.
you should have 2 molecules in the end.
Reactions of Ethers:
SN2 pathway to do list:
1. check for O to be attached to primary or secondary carbons. NOT Tert.
2. the X goes with the less hindered group
Reactions of Ethers:
SN1 pathway to do list:
1. Check for O to be attached to a tert carbon.
2. X goes with tert group
Cyclic Ethers: Epoxides (triangle with an O)
Epoxides into Alcohols: how easily can they be cleaved?
Very easily, they are unstable due to strain.
Cyclic Ethers: Epoxides
how are epoxides cleaved?
by an acid, base, grignard (RMgX), Nu:
Cyclic Ethers:Epoxides
Cleaved by HX what happens
OH in the opening and the X opposite side for trans stereochemistry
Cyclic Ethers:Epoxides
Cleaved by H3O+ what happens
OH in the opening and another OH in the trans position.
The Nature of Carbonyl Cmpds:
List the 2 groups of carbonyl compounds based on the chemistry they undergo:
1. Aldahydes and Ketones
2. Carboxylic Acids and derivites
The Nature of Carbonyl Cmpds:
Why are carboxylic acids better leaving groups than Aldehydes and ketones?
They are able to stabilize a negative charge.
Oxidation of Aldehydes:
What is the most common agent to convert aldehydes into carboxylic acids?
What do you get?
Aldehyde (NaBH4)-->
What do you get?
Ketone (NaBH4)-->
C-OH-C all single bonds, C bonded to an O which is bonded to the H and the C making an alcohol
What do you get?
Aldehyde (RMgX/H3O+)-->
an secondary alcohol
Nucleophilic Addition Reactions:
The alkoxide ion is protonated by?
Nucleophilic Addition Reactions:
What is the alkoxide ion
it is the intermediate under Basic conditions
Nucleophilic Add of Hydride and Grignard Reagents: Alcohol formation
Aldehydes with NaBH4 make a?
Ketones with NaBH4 makes a?
primary alcohol
secondary alcohol
Synthesis of Alcohols from Carbonyl cmpds:
Reduction of Aldehydes and Ketones:
NaBH4 and what solvent is used?
Nucleophilic Additon of Hydride & Grgnard Rxn: Alcohol Formation
Addition of Hydride (H-) Reagent: Reduction
NaBH4 and what solvent is used?
Ethanol H-O-R