Org Synthesis Quiz
-
Upload
lianchen251110 -
Category
Documents
-
view
93 -
download
0
Transcript of Org Synthesis Quiz
![Page 1: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/1.jpg)
A Level ChemistrySynthetic Routes
AS Chemistry: Slides 2-21A2 Chemistry: Slides 22-70
![Page 2: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/2.jpg)
You can convert an alkene to an alcohol by:
A.Adding concentrated H2SO4.
B.Adding dilute H2SO4 then add H2O.
C.Adding concentrated H2SO4 then add H2O and warm.D.Adding concentrated H2SO4 and warm.
![Page 3: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/3.jpg)
The mechanism of reaction between an alkene and concentrated H2SO4 to make an alcohol is:
A.Electrophilic substitution.B.Electrophilic addition followed by hydrolysisC.Hydrolysis.D.Nucleophilc addition followed by hydrolysis
![Page 4: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/4.jpg)
The major product formed when CH3CH=CH2 reacts with concentrated sulphuric acid followed by addition of water is:
A.CH3CH2CH2OH.
B.CH3CH(OH)CH3.
C.CH3CH(OH)CH2(OH)
![Page 5: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/5.jpg)
The reagent and mechanism to convert an alkene to haloalkane are:
A.X2 (X= halogen) in an electrophilic substitution
B.X2 in a nucleophilic addition.
C.HX in a nucleophilic additionD.HX in an electrophilic addition
![Page 6: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/6.jpg)
CH3
H
CH3
H
CC
OSO3H
H+
-
OSO3H
carbocation
2-butylhydrogensulphate
CH3
H H
CC
H
CH3
CH3
H H
CC
H OSO3H
CH3
How many mistakes are shown below?
A. One error. B= two errors C = three errors
![Page 7: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/7.jpg)
The reagents and conditions to convert a haloalkane (RX) to a nitrile RC≡N are:
A.HCN in a fume cupboardB.KCN in ethanol in fume cupboard.C.KCN in ethanol, heat in a fume cupboard.D.HCN and heat in a fume cupboard
![Page 8: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/8.jpg)
The name of CH3CN is:
A.methanitrileB.ethanitrileC.ethanenitrileD.methanenitrile
![Page 9: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/9.jpg)
To convert CH3CH2CN to CH3CH2COOH you need:
A.HCl and water (acid hydrolysis)
B.HCl and NH3
C. NaOH and water (alkaline hydrolysis)
![Page 10: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/10.jpg)
The reaction between a haloalkane and hot ethanolic KCN to produce a nitrile:
A.KCN is the nuclephileB.:CN- is the electrophileC.:CN- is the nucleophileD.KCN is involved in a neutralisation reaction
![Page 11: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/11.jpg)
The reagent, conditions and mechanism to convert a haloalkne into an alchol (e.g.CH3CH2Cl into CH3CH2OH) are:
A.Ethanolic NaOH in nuclephilic substitution.B.Ethanolic NaOH in nucleophilic elimination.C. NaOH aqueous, warm in nucleophilic addition.D.NaOH aqueous in nucleophilic substitution.
![Page 12: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/12.jpg)
The reagent, conditions and mechanism to convert a haloalkane into an alkene (e.g. CH3CH2Cl into CH2=CH2) are:
A.Ethanolic NaOH in an addition- elimination.B.NaOH aqueous in an addition- elimination.C.Ethanolic NaOH in an elimination, OH- as the
base.D.NaOH aqueous in an elimination with the OH- as
the base.
![Page 13: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/13.jpg)
The make a 10 amine from a haloalkane (e.g CH3CH2NH2 from CH3CH2Cl ) you need:
A.Excess haloalkane in a nucleophilc substitutionB.Excess NH3 in a nucleophilic substitution.
C.Excess NH3 in an electrophilc substitution.
![Page 14: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/14.jpg)
The name of CH3(CH3CH2)NH is
A.Methylethyl amine.B.AminopropaneC.Ethylmethyl amine.D.Propanamide
![Page 15: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/15.jpg)
How many mistakes are shown?
A= 4 error, B= 5 errors, C= more than 5 errors
aminoethane
CH3
H
BrC
H
Br-
H
CH3
H
NH2C
H
CH3
H
NH2C
H
NH3
H NH3+Br -
reaction equation
NH3
![Page 16: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/16.jpg)
a) Draw the mechanism for the reaction between bromoethane and the cyanide ion. Name the organic product formed.
b) Check your answer against the next slide.
![Page 17: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/17.jpg)
+ -CH3
H
BrC
H
CN -
CH3
H
CNC
H Br-
cyanide ion with bromoethane
Nucleophilic substitution mechanism
propanenitrile
reaction equation
![Page 18: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/18.jpg)
a) Draw the mechanism to show the reaction between 2-bromopropane and NaOH (in ethanol).
b) Compare your answer against the next slide.
![Page 19: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/19.jpg)
Elimination of HBr from 2-bromopropane
CH3
H H
H
CC
OH -
CH3
H H
HCC
Br H
propene
H OHBr -
CH3CHBrCH3 + OH- CH3CH=CH2 + H2O + Br-
(in ethanol)
acting as a base
Elimination of HX from haloalkanes
![Page 20: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/20.jpg)
The reagents and conditions to convert CH3CH2CH2OH to CH3CH2CHO are:
A.Acidified potassium dichromate K2Cr2O7 , heat and reflux.
B.Add Tollen’s reagent until you get a silver mirror.
C.Acidified K2Cr2O7 heat and distil.
D.Add aqueous NaBH4
![Page 21: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/21.jpg)
Alcohols can be converted into alkenes by:
A.An elimination reaction using concentrated H2SO4 as a catalyst (dehydration).
B.An elimination reaction using concentrated H2SO4 as a catalyst (hydrolysis).
C.An addition reaction using H2O and concentrated H2SO4 as a catalyst.
![Page 22: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/22.jpg)
CH3
C= O to CH3CH2OH using:
H
A.NaBH4 (aq) as the oxidising agent
B.NaBH4 (aq) as the reducing agent.
![Page 23: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/23.jpg)
The mechanism of reactions exhibited by aldehydes and ketones is:
A.Electrophilic addition.B.Electrophilic substituion.C.Nucleophilc substituion.D.Nucleophilic addition.
![Page 24: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/24.jpg)
The reagent and conditions to convert RCHO to RCH2OH or a R1R2CO to R1CH(OH)R2
A.NaBH4 (aq) with NaBH4 as the nucleophile.
B.NaBH4 (aq) with BH4 as the nucleophile.
C.NaBH4 (aq) with :H- hydride ion as the nucleophile
![Page 25: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/25.jpg)
(a) Draw the mechanism for the reaction between propanone and sodium tetrahydridoborate NaBH4.
(b) Check you answer against the following slide.(c) What type of mechanism is it?
![Page 26: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/26.jpg)
+
-
reduction of propanone
H+
NaBH4 is a source of hydride ions
CH3
CH3
C
O
CH3
CH3
C
O
H
H
propan-2-ol
H
CH3
CH3
C
O
H
H
from the solvent
![Page 27: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/27.jpg)
The name of CH3CH(OH) CN is:
A.2-hydroxyethanitrile.B.2-hydroxypropanitrile.C.Butan-2-ol.D.2-hydroxypropanenitrile.
![Page 28: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/28.jpg)
The name of CH3CH(OH) CH2 COOH
A.2-hydroxybutanoic acid.B.3-hydroxybutaneoic acid.C.3-hydroxybutanoic acid.D.2-hydroxycarboxylic acid.
![Page 29: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/29.jpg)
The reagent and conditions to convert RCHO to2-hydroxynitrile RCH(OH)CN then to a 2-
hydroxycarboxylic acid are:
A.KCN (aq) and H2SO4 in a fume cupboard, followed by acid hydrolysis.
B.HCN in a fume cupboard, followed by acid hydrolysis.
C.HCN and H2SO4 in a fume cupboard, followed by acid hydrolysis
![Page 30: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/30.jpg)
(a) Draw the mechanism of the reaction between propanone and the cyanide ion as the nucleophile. Name the organic product.
(b) Check your answer against the next slide.
![Page 31: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/31.jpg)
Nucleophilic Addition Mechanismhydrogen cyanide with propanone
H+
NaCN (aq) is a source of cyanide ions
CH3COCH3 + HCN CH3C(OH)(CN)CH3
CH3
CH3
C
O
CH3
CH3
C
O
CN
H
H+
2-hydroxy-2-methylpropanenitrile
from H2SO4 (aq)
+
-
CN
C N
CH3
CH3
C
O
CN
![Page 32: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/32.jpg)
• Explain why, in a laboratory synthesis, the reaction between ethanal and :CN- gives rise to a racemic mixture.
![Page 33: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/33.jpg)
Recap: How can you can carry out the following conversion?
Alkene Alcohol ketonee.g. Propene propan-2-ol propanone
![Page 34: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/34.jpg)
Haloalkane Nitrile 10 Amine
CH3CH2Cl CH3CH2CN CH3CH2CH2NH2
Step 1: Reflux haloalkne with ethanolic solution of KCN
Step 2: Reduction using H2/Nickel catalyst
![Page 35: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/35.jpg)
How would you carry out the following conversions?
10 Alcohol Aldedyde Carboxylic Acid
Ester
![Page 36: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/36.jpg)
The compound CH3CH(CH3)CH2COOH is:
A.2-methylbutanoic acid.B.3-methyl butanoic acidC.Pentanoic acid
![Page 37: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/37.jpg)
The compound O CH3 C
OCH2CH2CH(CH3)2
A.Methyl pentanoateB.2-methylbutyl ethanoateC.3-methylbutyl ethanoateD.3-methylbutyl methanoate
![Page 38: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/38.jpg)
The reagents to make HCOOCH2CH3 are:
A. CH3CH2COOH and CH3OH
B. HCOOH and CH3CH2OH
C. HCOONa and CH3CH2OH
![Page 39: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/39.jpg)
The products of the alkaline hydrolysis of esters:RCOOR’ + NaOH →
A.RCOOH + R’ONaB. RCOO-Na+ + R’OHC.RCOH + R’OONa
![Page 40: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/40.jpg)
The name of HCOO-Na+ is:
A.Methanoic sodiumB.Sodium methanoateC.Sodium methanoic acid
![Page 41: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/41.jpg)
The following is the preferred method to regenerate the carboxylic acid as it:
RCOOR’ + NaOH RCOO-Na+ + R’OH HCl RCOOH + NaCl A.Uses non-toxic raw materials.B.Gives higher yieldC.It’s a faster reaction
![Page 42: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/42.jpg)
Name the compound CH3CH2COCl
propanoyl chloride
![Page 43: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/43.jpg)
Complete the following general equations and state the type of mechansim.
RCOCl + H2O →
RCOCl + R’OH →RCOCl + NH3 →
RCOCl + RNH2 →
Nucleophilic addition-elimination
![Page 44: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/44.jpg)
The name of CH3CH2CONH2 is:
A.Propyl amineB.PropaneamideC.N-ethylethanamideD.Propanamide
![Page 45: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/45.jpg)
State the reagents and conditions for makingCH3COOCH3 starting with an acyl chloride.
CH3COCl ethanoyl chloride and CH3OH methanol. Anhydrous conditions.
![Page 46: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/46.jpg)
Give the formula, conditions used and name of the organic product for:CH3COCl + CH3CH2CH2NH2 →
CH3CONHCH2CH2CH3
N-PropylethanamideAnhydrous conditions
![Page 47: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/47.jpg)
Complete the following reaction. State the conditions, and name of the organic product formed.CH3CH2COCl + NH3 →
→ CH3CH2CONH2 + NH4Cl
PropanamideUse excess NH3
NH3 first behaves as a nucleophile , then as a base (proton acceptor).
![Page 48: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/48.jpg)
A) Write the mechanism for the reaction between ethanoyl chloride and propanol. Name the organic product formed.
B) Compare your answer against the next slide.
![Page 49: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/49.jpg)
+
-
Nucleophilic Addition Elimination Mechanism
CH3
Cl
C
O
OCH2CH2CH3
H
CH3
Cl
C
O
OCH2CH2CH3
H
+
CH3C
O
OCH2CH2CH3
H
+
CH3C
O
OCH2CH2CH3 Cl
nucleophilic addition
elimination
reaction equation
H-Cl
![Page 50: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/50.jpg)
Name the compound (CH3CH2CO)2O
Propanoic anydride
![Page 51: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/51.jpg)
Write an equation to show how ethanoic anhydride is formed.
![Page 52: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/52.jpg)
Complete the following equation and name the products formed.
(CH3CH2CO)2O + CH3OH →
→ CH3CH2COOCH3 + CH3CH2OH
methylpropanoate and ethanol
![Page 53: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/53.jpg)
a) State the three methods for making esters.b)Compare the methods mentioned in (a)
![Page 54: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/54.jpg)
Draw the mechanism for the reaction between an acid chloride RCOCl and excess NH3.
State the role of NH3
Compare your answer against the next slide.
![Page 55: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/55.jpg)
+
-
Nucleophilic Addition Elimination Mechanism
R
Cl
C
O
NH2
H
R
Cl
C
O
NH2
H
+
R C
O
NH2
H
+
Cl NH3
R C
O
NHCH2CH2CH3
H
+ NH3
Cl
nucleophilic addition
elimination
reaction equation
![Page 56: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/56.jpg)
Name the compound: CH2CH3
CH3 N
H
Ethylmethylamine
![Page 57: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/57.jpg)
Name the compound CH3CHCH3
NH2
2-aminopropane
![Page 58: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/58.jpg)
Name the compound CH3
CH3CHCH2NH2
1-amino,2-methylpropane
![Page 59: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/59.jpg)
Recall the two methods for making amines:a)RX + NH3 (excess) →
b)Reduction of nitriles RCN
Why must NH3 be in excess?What is the reducing agent in (b)?
![Page 60: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/60.jpg)
Write equations for the reaction between excess CH3CH2Br and NH3.
Name all the organic products formed.
![Page 61: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/61.jpg)
Identify the organic product and state its uses:(CH3CH2)4N+Br-.
Quaternary ammonium saltUsed as cationic surfactant in fabric conditioners
and shampoos to reduce static.
![Page 62: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/62.jpg)
State the reagents and conditions for the following reaction. Name the organic product.
C6H6 → C6H5NO2
Concentrate HNO3 and concentrated H2SO4
Temperature: 500C
![Page 63: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/63.jpg)
Benzene C6H6 undegoes:
A. Electrophilic addition.B. Nucleophilic addition.C. Electrophilic substitution.D. Nucleophilic addition-elimination
![Page 64: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/64.jpg)
a) Name the electrophile in the nitration of benzene.
b) Write relevant equations to show how this electophile is formed.
NO2+ nitronium ion.
H2SO4 + HNO3 ↔ HSO4- + H2NO3
+ then,
H2NO3+ → H2O + NO2
+
![Page 65: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/65.jpg)
Draw the mechanism for the nitration of benzeneCompare you answer against the next slide.
![Page 66: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/66.jpg)
Electrophilic substitution mechanism (nitration)
2. Electrophilic attack on benzene
NO2
NO2
+
3. Forming the product
+
NO2
H
reaction equation
and re-forming the catalyst
![Page 67: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/67.jpg)
Name the reagnets and condtiosn fro the reaction C6H6 → C6H5COCH3
CH3COCl Ethanoyl chloride
AlCl3 aluminium chloride catalyst
Anhydrous conditionsTemperature: 0-250C
![Page 68: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/68.jpg)
a) Write an overall equation to show the reaction between C6H6 and CH3COCl
b)Show how the electrophile is formed.b)State the role of AlCl3 in the acylation of
benzene.
![Page 69: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/69.jpg)
CH3C Cl
O
Acylation example
Three steps in electrophilic substitution mechanism
1. Formation of the electrophile (an acylium ion).
2. AlCl3 behaves as a Lewis acid
AlCl3 [AlCl4] -
With ethanoyl chloride overall reaction equation
C6H6 + CH3COCl C6H5COCH3 + HCl
+CH3C
O
![Page 70: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/70.jpg)
Draw a mechanism for the reaction between benzene and CH3COCl.What type of mechanism is it?
Compare your answer against the next slide.
![Page 71: Org Synthesis Quiz](https://reader033.fdocuments.in/reader033/viewer/2022061618/55cf9a28550346d033a0aa4e/html5/thumbnails/71.jpg)
+H
CH3C
O
Acylation electrophilic substitution mechanism 2
2. Electrophilic attack on benzene
phenylethanone
-Cl AlCl3
AlCl3 + H Cl
3. Forming the product
and re-forming the catalyst
+CH3C
O
CH3C
O
+ H+