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rich
In an EAS mechanism, electron (rich/poor) benzene rings are needed to attack the electrophile.
resonance
Which has a larger influence how electron rich a benzene ring is, resonance or inductive effect?
Resonance and Inductive Effect
What are the two factors that can influence how electron rich or electron poor a benzene ring is?
more
Resonance structures pushing electrons into the ring means that the benzene ring will be (more/less) electron rich
less
Resonance structures pulling electrons out of the ring means that the benzene ring will be (more/less) electron rich
increased
Electron density (richness) can be (increased/decreased) by adjacent electron rich atoms or bonds
decreased
Electron density (richness) can be (increased/decreased) by adjacent electronegative atoms or groups.
More
Is this benzene derivative more or less reactive for EAS reactions?
less
Is this benzene derivative more or less reactive for EAS reactions?
phenol, more
Name this benzene derivative and determine if it is more/less reactive for EAS.
more
Determine if this benzene derivative is more/less reactive for EAS.
Analine, more
Name this benzene derivative and determine if it is more/less reactive for EAS.
less
Determine if this benzene derivative is more/less reactive for EAS.
less
Determine if this benzene derivative is more/less reactive for EAS.
nitrobenzene, less
Name this benzene derivative and determine if it is more/less reactive for EAS.
less
Determine if this benzene derivative is more/less reactive for EAS.
less
Determine if this benzene derivative is more/less reactive for EAS.
negative
For an EAS mechanism, electron rich benzene derivatives end with a product with a (positive/negative) charge on the benzene ring.
positive
For an EAS mechanism, electron poor benzene derivatives end with a product with a (positive/negative) charge on the benzene ring.
are
Halogens (are/are not) very electronegative
less
A benzene with a halogen directly attached is (more/less) reactive for EAS
false
True/False: Halogens have resonance away, which is why they are less reactive for EAS.
true
True/False: Halogens have inductive away, which is why they are less reactive for EAS.
more
Alkyl groups offer (more/less) electron density
more
A benzene ring with an alkyl group directly attached is (more/less) reactive for EAS.
resonance towards, inductive towards, benzene, inductive away, resonance away
List the most to least reactive characteristics of molecules for EAS.
inductive away, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive away, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
NO2
What group, when attached to a benzene ring, are the WORST for EAS?
resonance away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive away, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
resonance away, meta
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive towards, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
1
(use 1, 2, 3, or 4)
inductive away, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive away, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
inductive away, ortho/para
Name the characteristics of this molecule that relate to its reactivity in EAS as well as what type of director it is.
1, having 2 halogens increases electronegativity and pulls electrons away
Which is more active for EAS? (1 or 2), and why?
1, Fluorine is more electronegative than Cl and has a stronger pull away of the electrons
Which is more active for EAS? (1 or 2), and why?
4
(use 1, 2, 3, 4, or 5)
4, 2, 5, 1, 3
Place the following from most to least active for EAS. (use 1, 2, 3, 4, and 5)
Major product 1 (most abundant): para-chlorobromobenzene
Major product 2: ortho-chlorobromobenzene
Describe the major product(s) of the reaction. If there are more than one, denote which one is the most abundant.
meta-nitrobromobenzene
Describe the major product(s) of the reaction. If there are more than one, denote which one is the most abundant.
meta-(functional group)bromobenzene
Describe the major product(s) of the reaction. If there are more than one, denote which one is the most abundant.
Major product 1 (most abundant): para-isobutylbromobenzene
Major product 2: ortho-isobutylbromobenzene
Describe the major product(s) of the reaction. If there are more than one, denote which one is the most abundant.
Major product 1 (most abundant): para-(functional group)bromobenzene
Major product 2: ortho-(functional group)bromobenzene
Describe the major product(s) of the reaction. If there are more than one, denote which one is the most abundant.
Step 1: Nitrobenzene
Step 2: meta-nitrochlorobenzene
Describe the major product(s) of each step of the reaction.
Step 1: Chlorobenzene
Step 2:
Major product 1: ortho-chloronitrobenzene
Major product 2: para-chloronitrobenzene
Describe the major product(s) of each step of the reaction.
true
True/False: When making benzene derivatives, the order of reactions determines what product is formed.
no
In EAS mechanisms with an ortho/para director, do we always expect an equal mixture of ortho and para products?
statistics and sterics
What two factors are important when determining the amount of ortho and para products produced in an EAS mechanism with an ortho/para director?
ortho (twice as many chances to go ortho vs para)
Statistically speaking, which product is formed more in an EAS reaction with an ortho/para director, the ortho or the para product?
Para (ortho could be very crowded if dealing with a highly branched substituent.)
Sterically speaking, which product is formed more in an EAS reaction with an ortho/para director, the ortho or the para product?
1-methoxyl,2-chloro,4-nitrobenzene
Predict the product(s) of the following reaction if X is OCH3 (methoxyl group) and Y is NO2.
1-methoxyl,2-chloro,4-nitrobenzene
Predict the product(s) of the following reaction if X is OCH3 (methoxyl group) and Y is CH3.
the most activated wins
If there are multiple groups on the benzene ring that direct the reaction to a different position (ortho/meta/para), which one wins?
Major Product (least sterically crowded): 1-(SO3H group),2-methyl,4-bromobenzene
Medium Product: 1-(SO3H group),2-bromo,3-methylbenzene
Minor Product (most sterically crowded): 1-bromo,2-(SO3H group),3-methylbenzene
What is the product(s) of the following reaction? If there are more than one, denote which one is the major product.
meta-nitrobenzoic acid
What is the major product(s) of the following reactions? If there are more than one, denote which one is the major product.
Major Product 1(most abundant): para-isopropylchlorobenzene
Major Product 2: ortho-isopropylchlorobenzene
What is major the product(s) of the following reaction? If there are more than one, denote which one is the most abundant.
1,4-dimethyl,2-(acetyl chloride group)benzene
What is major the product(s) of the following reaction? (Acetyl chloride is a ketone with one R group as CH3 and the other as Cl) If there are more than one, denote which one is the most abundant.
No reaction (Freidl-Crafts cannot occur due to the nitro group)
What is major the product(s) of the following reaction? If there are more than one, denote which one is the most abundant.
Major product 1 (more abundant): para-(SO3H group)phenol
Major product 2: ortho-(SO3H group)phenol
What is major the product(s) of the following reaction? If there are more than one, denote which one is the most abundant.
Major product 1 (more abundant): para-ethylbromobenzene
Major product 2: ortho-ethylbromobenzene
What is major the product(s) of the following reactions? If there are more than one, denote which one is the most abundant.
adding just a halogen (eg Cl2, FeCl3)
When reacting a nitrobenzene through EAS, which reaction pathway does not terminate the reaction?
1) Benzene + H2SO4 and SO3
2) + Cl2 and FeCl3
How can you synthesize m-chlorobenzenesulfonic acid from benzene?
1) Benzene + Acetyl chloride (Acetyl chloride is a ketone with one R group as CH3 and the other as Cl)
2) + Cl2 and FeCl3
3) + Heat and NH2NH2 and OH-
How can you synthezise m-chloroethylbenzene from benzene?
Aldehyde
Name the functional group shown
Ketone
Name the functional group shown.
C-H and C-C
In reactions with ketones and aldehydes, which bonds “stay as is” and don’t react away?
Aldehydes
Which are more reactive, aldehydes or ketones?
strong
C-C and C-H bonds are (strong/weak)
weakly
C-C and C-H bonds are (strongly/weakly) polarized
hard
C-C bonds and C-H bonds are (easy/hard) to break
difficult
Substitution of H or R groups on aldehydes and ketones is (easy/difficult)
true
True/False: When naming aldehydes, you do not need to but a number as a prefix to signify where the carbonyl group is at
False
True/False: When naming ketones, you do not need to but a number as a prefix to signify where the carbonyl group is at
-al
What suffix gets added to the end of aldehydes?
-one
What suffix gets added to the end of ketones?
carbonyl
When naming a ketone with an alcohol group, which gets priority in the numbering system, the carbonyl or alcohol?
True
True/False: When naming aldehydes, the carbonyl carbon is always the “1” carbon
Butanal
Name the following structure:
2-pentanone
Name the following structure:
4-hydroxybutanal
Name the following structure:
4-hydroxy-2-pentanone
Name the following structure:
Draw the following structure: 2,4-pentanedione
Draw the following structure: 4-hexenal
Draw the following structure: 4-bromo-3-heptanone
Draw the following structure: 3-methylcyclohexanone
Note 
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