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.
The mechanism of reaction between an alkene and concentrated H2SO4 to make an alcohol is: A. B. C. D. Electrophilic substitution. Electrophilic addition followed by hydrolysis Hydrolysis. Nucleophilc addition followed by hydrolysis
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)
A. B. C. D.
X2 (X= halogen) in an electrophilic substitution X2 in a nucleophilic addition. HX in a nucleophilic addition HX in an electrophilic addition
H
C H
carbocation
CH3
+ H
OSO3H
OSO3H
H CH3 2-butylhydrogensulphate C H
H C CH3
OSO3H
The reagents and conditions to convert a haloalkane (RX) to a nitrile RCN are: A. B. C. D. HCN in a fume cupboard KCN in ethanol in fume cupboard. KCN in ethanol, heat in a fume cupboard. HCN and heat in a fume cupboard
To convert CH3CH2CN to CH3CH2COOH you need: A. HCl and water (acid hydrolysis) B. HCl and NH3 C. NaOH and water (alkaline hydrolysis)
The reaction between a haloalkane and hot ethanolic KCN to produce a nitrile: A. B. C. D. KCN is the nuclephile :CN- is the electrophile :CN- is the nucleophile KCN is involved in a neutralisation reaction
The reagent, conditions and mechanism to convert a haloalkne into an alchol (e.g.CH3CH2Cl into CH3CH2OH) are: A. B. C. D. Ethanolic NaOH in nuclephilic substitution. Ethanolic NaOH in nucleophilic elimination. NaOH aqueous, warm in nucleophilic addition. NaOH aqueous in nucleophilic substitution.
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 OHas the base.
The make a 10 amine from a haloalkane (e.g CH3CH2NH2 from CH3CH2Cl ) you need: A. Excess haloalkane in a nucleophilc substitution B. Excess NH3 in a nucleophilic substitution. C. Excess NH3 in an electrophilc substitution.
H NH3
H
CH3
aminoethane
C H
NH2 H NH3+Br
reaction equation
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.
H + CH3 C H CN Br CH3
H C CN Br-
H
propanenitrile
reaction equation
a) Draw the mechanism to show the reaction between 2-bromopropane and NaOH (in ethanol). b) Compare your answer against the next slide.
H CH3 C Br
H C H H
H C C
H propene H
Br
CH3
OH
H OH
acting as a base
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.
CH3
C= O
H
to CH3CH2OH using:
A. NaBH4 (aq) as the oxidising agent B. NaBH4 (aq) as the reducing agent.
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
(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?
reduction of propanone NaBH4 is a source of hydride ions O C CH3 H CH3 C CH3 H CH3 H from the solvent O H+ O C CH3 propan-2-ol H H
CH3
A. B. C. D.
The reagent and conditions to convert RCHO to 2-hydroxynitrile RCH(OH)CN then to a 2hydroxycarboxylic 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
(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.
H+
CH3
2-hydroxy-2-methylpropanenitrile
Explain why, in a laboratory synthesis, the reaction between ethanal and :CN- gives rise to a racemic mixture.
Recap: How can you can carry out the following conversion? Alkene Alcohol ketone e.g. Propene propan-2-ol propanone
Haloalkane
Nitrile
10 Amine
CH3CH2Cl
CH3CH2CN
CH3CH2CH2NH2
Step 1: Reflux haloalkne with ethanolic solution of KCN Step 2: Reduction using H2/Nickel catalyst
How would you carry out the following conversions? 10 Alcohol Aldedyde Carboxylic Acid Ester
The compound CH3CH(CH3)CH2COOH is: A. 2-methylbutanoic acid. B. 3-methyl butanoic acid C. Pentanoic acid
The compound O CH3 C OCH2CH2CH(CH3)2 A. B. C. D. Methyl pentanoate 2-methylbutyl ethanoate 3-methylbutyl ethanoate 3-methylbutyl methanoate
The reagents to make HCOOCH2CH3 are: A. CH3CH2COOH and CH3OH B. HCOOH and CH3CH2OH C. HCOONa and CH3CH2OH
The products of the alkaline hydrolysis of esters: RCOOR + NaOH A. RCOOH + RONa B. RCOO-Na+ + ROH C. RCOH + ROONa
The name of HCOO-Na+ is: A. Methanoic sodium B. Sodium methanoate C. Sodium methanoic acid
The following is the preferred method to regenerate the carboxylic acid as it: RCOO-Na+ + ROH HCl RCOOH + NaCl A. Uses non-toxic raw materials. B. Gives higher yield C. Its a faster reaction RCOOR + NaOH
Complete the following general equations and state the type of mechansim. RCOCl + H2O RCOCl + ROH RCOCl + NH3 RCOCl + RNH2
Nucleophilic addition-elimination
State the reagents and conditions for making CH3COOCH3 starting with an acyl chloride. CH3COCl ethanoyl chloride and CH3OH methanol. Anhydrous conditions.
Give the formula, conditions used and name of the organic product for: CH3COCl + CH3CH2CH2NH2 CH3CONHCH2CH2CH3 N-Propylethanamide Anhydrous conditions
Complete the following reaction. State the conditions, and name of the organic product formed. CH3CH2COCl + NH3
CH3CH2CONH2 + NH4Cl Propanamide Use excess NH3 NH3 first behaves as a nucleophile , then as a base (proton acceptor).
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.
+
H
OCH2CH2CH3
Cl
elimination
+
H
OCH2CH2CH3 Cl
H-Cl
reaction equation
Complete the following equation and name the products formed. (CH3CH2CO)2O + CH3OH
CH3CH2COOCH3 + CH3CH2OH methylpropanoate and ethanol
a) State the three methods for making esters. b)Compare the methods mentioned in (a)
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.
+
H
NH2
Cl
elimination
+
H
NH2 Cl
NH3
reaction equation
CH3 CH3CHCH2NH2
1-amino,2-methylpropane
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)?
Write equations for the reaction between excess CH3CH2Br and NH3. Name all the organic products formed.
Identify the organic product and state its uses: (CH3CH2)4N+Br-. Quaternary ammonium salt Used as cationic surfactant in fabric conditioners and shampoos to reduce static.
State the reagents and conditions for the following reaction. Name the organic product. C6H6 C6H5NO2 Concentrate HNO3 and concentrated H2SO4 Temperature: 500C
Benzene C6H6 undegoes: A. B. C. D. Electrophilic addition. Nucleophilic addition. Electrophilic substitution. Nucleophilic addition-elimination
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+
Draw the mechanism for the nitration of benzene Compare you answer against the next slide.
NO2 +
NO2
H NO2
reaction equation
Name the reagnets and condtiosn fro the reaction C6H6 C6H5COCH3 CH3COCl Ethanoyl chloride AlCl3 aluminium chloride catalyst Anhydrous conditions Temperature: 0-250C
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.
Acylation example
With ethanoyl chloride overall reaction equation
C6H6 + CH3COCl
C6H5COCH3
+ HCl
Three steps in electrophilic substitution mechanism 1. Formation of the electrophile (an acylium ion). 2. AlCl3 behaves as a Lewis acid O CH3C Cl AlCl3 + CH3C
O [AlCl4] -
Draw a mechanism for the reaction between benzene and CH3COCl.What type of mechanism is it? Compare your answer against the next slide.
Cl
AlCl3
+ H+
AlCl3 +
Cl