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IUPAC Naming and Reaction Mechanisms

The document contains 15 multiple choice questions about organic chemistry nomenclature and reactions. Specifically, it tests identification of IUPAC names, functional groups, reaction mechanisms (SN1, SN2, E1, E2), types of reactions (hydrolysis, substitution, elimination, addition), organic products, polymers and their synthesis. It also contains questions about reaction pathways, stereoisomers, effects of reaction conditions on rate, and comparison of reactivities of different halogenoalkanes.

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0% found this document useful (0 votes)
106 views10 pages

IUPAC Naming and Reaction Mechanisms

The document contains 15 multiple choice questions about organic chemistry nomenclature and reactions. Specifically, it tests identification of IUPAC names, functional groups, reaction mechanisms (SN1, SN2, E1, E2), types of reactions (hydrolysis, substitution, elimination, addition), organic products, polymers and their synthesis. It also contains questions about reaction pathways, stereoisomers, effects of reaction conditions on rate, and comparison of reactivities of different halogenoalkanes.

Uploaded by

minji
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as RTF, PDF, TXT or read online on Scribd

1. What is the IUPAC name of CH3CH2CONH2?

A. Aminopropanal

B. Ethanamide

C. Propylamine

D. Propanamide
(Total 1 mark)

2. What is the IUPAC name for the following compound?

CH3(CH2)2COOCH3

A. Methyl butanoate

B. Butyl ethanoate

C. Butyl methanoate

D. Methyl propanoate
(Total 1 mark)

3. Identify the functional group present in HCOCH2CH3.

A. Ester

B. Ketone

C. Aldehyde

D. Alcohol
(Total 1 mark)

IB Questionbank Chemistry 1
4. What is the IUPAC name for HCOOCH2CH2CH3?

A. Butanoic acid

B. Butanal

C. Methyl propanoate

D. Propyl methanoate
(Total 1 mark)

5. What is the IUPAC name of the compound CH3CH2COOCH2CH3?

A. Ethyl ethanoate

B. Propyl ethanoate

C. Ethyl propanoate

D. Pentyl propanoate
(Total 1 mark)

6. What is the correct IUPAC name for the following compound?


CH 3CHCH 2CH 2CN

CH 3

A. 4-methylbutanenitrile

B. 4-methylpentanenitrile

C. 2-methylbutanenitrile

D. 2-methylpentanenitrile
(Total 1 mark)

IB Questionbank Chemistry 2
7. 2-chloro-3-methylbutane reacts with sodium hydroxide via an SN2 mechanism.
Explain the mechanism by using curly arrows to represent the movement of electron
pairs.

(Total 4 marks)

8. (a) Below are four structural isomers with molecular formula C4H9Br. State the
name of each of the isomers A, B, C and D.

(4)

IB Questionbank Chemistry 3
IB Questionbank Chemistry 4
(b) (i) Identify the isomer(s) which will react with aqueous sodium hydroxide
almost exclusively by an SN1 mechanism. State the meaning of the symbols
in the term SN1 mechanism.
(2)

(ii) Using the formula RBr to represent a bromoalkane, state an equation for the
rate determining step of this SN1 reaction.
(1)

(iii) Identify one isomer that will react with aqueous sodium hydroxide almost
exclusively by an SN2 mechanism. Draw the mechanism for this reaction
using curly arrows to represent the movement of electron pairs. Include the
structural formulas of the transition state and the organic product.
(4)

(c) State and explain how the rates of the reactions in parts (b) (i) and (b) (iii) are
affected when the concentration of the sodium hydroxide is doubled.
(2)

(d) State and explain how the rate of reaction of 1-bromobutane with sodium
hydroxide compares with that of 1-chlorobutane with sodium hydroxide.
(2)

(e) Identify the isomer of C4H9Br that can exist as stereoisomers. Outline how a
polarimeter will distinguish between the isomers, and how their physical and
chemical properties compare.
(5)

(f) (i) State the type of reaction that occurs when isomer B, CH3CHBrCH2CH3,
reacts with a hot alcoholic solution of sodium hydroxide.
(1)

(ii) Explain how the reaction in part (f) (i) occurs by drawing the mechanism,
using curly arrows to represent the movement of electron pairs and identify
the two possible organic products.
(4)
(Total 25 marks)

IB Questionbank Chemistry 5
9. The reaction between bromoethane, CH3CH2Br, and potassium cyanide is an example of
a nucleophilic substitution reaction.

(i) State whether this reaction is SN1 or SN2.


(1)

(ii) Explain the mechanism of the reaction using curly arrows to represent the
movement of electron pairs.
(4)

(iii) The organic product obtained in part (ii) can be reduced to form an amine.
State an equation for the reaction, naming the catalyst involved.
(2)
(Total 7 marks)

10. Bromoethane reacts with potassium hydroxide to undergo mainly a substitution


reaction or an elimination reaction depending on the reaction conditions used.

(i) State an equation and the reaction conditions used to control the products
formed in each case.
(4)

(ii) Explain the mechanism of the elimination reaction using curly arrows to
represent the movement of electron pairs.
(4)

(iii) Under certain conditions, the major product obtained in the elimination
reaction can undergo polymerization. Identify the type of polymerization this
major product undergoes.
(1)
(Total 9 marks)

11. (i) Describe the elimination of HBr from bromoethane. Your answer should
include the reagents, conditions and equation for the reaction.
(3)

IB Questionbank Chemistry 6
IB Questionbank Chemistry 7
(ii) Explain the mechanism for the elimination of HBr from bromoethane.
(5)
(Total 8 marks)

12. The compounds H2NCH2CH2NH2 and HOOCCH2COOH react to form a polymer. What
is the structure of the repeating unit of the polymer?

A. ( HNCH2CONHCH2CH2NHCO )

B. ( HNCH2CH2NHCOCH2CO )

C. ( OCCH2CONHCH2NHCO )

D. ( HNCH2CH2NHCOCH2NH )
(Total 1 mark)

13. Which process can produce a polyester?

A. Addition polymerization of a dicarboxylic acid

B. Condensation polymerization of a diol and a dicarboxylic acid

C. Addition polymerization of a diol and dicarboxylic acid

D. Condensation polymerization of a dicarboxylic acid


(Total 1 mark)

14. What is the organic product of the reaction between ethanol and ethanoic acid in the
presence of sulfuric acid?

A. CH3CHO

B. CH3COOCH3

C. CH3CH2COOCH3

D. CH3COOCH2CH3
(Total 1 mark)

IB Questionbank Chemistry 8
15. Halogenoalkanes undergo two major types of reaction leading to the formation of
different organic compounds.

(i) 1-bromopropane can be converted to 1-butylamine (butan-1-amine) in two


stages.
Draw the structural formulas of 1-bromopropane and 1-butylamine (butan-
1-amine).
(1)

(ii) Deduce a reaction pathway for the two-stage conversion of 1-bromopropane


to 1-butylamine (butan-1-amine). Your answer should include an equation for
each stage of the reaction and the reaction conditions for the second stage.
(4)
(Total 5 marks)

16. Which molecule has a chiral centre?

A. CH3CH=CHCHO

B. (CH3)2C=CHCH2OH

C. CH3OCH2CH3

D. CH3CHOHCH2CH3
(Total 1 mark)

17. How many chiral carbon atoms are present in a molecule of 2,3-dibromobutane?

A. 1

B. 2

C. 3

D. 4
(Total 1 mark)

IB Questionbank Chemistry 9
18. Which compound is optically active?

(Total 1 mark)

19. (i) Describe geometrical isomerism.


(1)

(ii) Draw the geometrical isomers of but-2-ene.


(2)

(iii) Draw the two enantiomers of butan-2-ol.


(2)
(Total 5 marks)

IB Questionbank Chemistry 10

Common questions

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The major product of the elimination reaction of bromoethane under appropriate conditions can undergo addition polymerization. This type of polymerization requires a monomer with a carbon-carbon double bond, which acts as the reactive site. The reaction conditions typically necessitate the presence of a catalyst and a certain temperature range to initiate the polymerization chain reaction .

The elimination reaction of bromoethane with potassium hydroxide is favored in the presence of a strong base, high temperature, and an alcoholic solvent. Under these conditions, an alkene (ethyl alkene) is formed as the hydrogen and bromine are eliminated, resulting in a double bond. In contrast, substitution reactions are favored under milder conditions and aqueous solvents .

But-2-ene exhibits geometrical isomerism, also known as cis-trans isomerism. This type of isomerism occurs due to restricted rotation around the double bond, resulting in two distinct forms: the cis isomer, where similar or higher priority groups are on the same side, and the trans isomer, where these groups are on opposite sides. These isomers can be visually represented by drawing the differences in spatial arrangements around the double bond .

In an SN2 mechanism for the reaction of 2-chloro-3-methylbutane with sodium hydroxide, the nucleophile, hydroxide ion (OH^-), approaches the substrate carbon from the backside, opposite to the leaving group (chloride ion, Cl^-). This results in a concerted, one-step reaction where the bond between carbon and chloride breaks, and a new bond is formed between the carbon and hydroxide ion. This leads to the inversion of configuration at the carbon center .

A polarimeter distinguishes between stereoisomers by measuring the angle of rotation of plane-polarized light they impart. Stereoisomers, specifically enantiomers, will rotate polarized light by equal amounts but in opposite directions. This property is due to the presence of chiral centers, which affect the path of polarized light, causing one stereoisomer to rotate light clockwise (dextrorotatory) and the other counterclockwise (levorotatory).

2,3-dibromobutane contains two chiral centers, located at the second and third carbon atoms of the butane chain. These chiral centers exist because each carbon atom is bonded to four different substituents. The presence of these centers enables the compound to exist in multiple stereoisomeric forms, including enantiomers, which can rotate plane-polarized light .

In an SN1 reaction, the rate is not affected by the concentration of sodium hydroxide because the rate-determining step involves only the dissociation of the leaving group to form a carbocation. Conversely, in an SN2 reaction, the reaction rate is directly proportional to the concentration of both the substrate and the nucleophile; thus, doubling the concentration of sodium hydroxide would double the reaction rate .

CH3CH2CONH2 is named propanamide according to IUPAC nomenclature. The structure contains a carbonyl group (C=O) bonded to a nitrogen atom (NH2), which identifies it as an amide. The longest carbon chain consists of three carbon atoms, leading to the prefix 'prop-' for propane. Hence, it is named propanamide .

The reaction between H2NCH2CH2NH2 (ethylenediamine) and HOOCCH2COOH (malonic acid) forms a polymer via condensation polymerization. The repeating unit of the resulting polymer is (HNCH2CH2NHCOCH2CO). The amine groups of ethylenediamine react with the carboxylic acid groups of malonic acid, releasing water and forming amide linkages .

The compound CH3CH2COOCH2CH3 is named ethyl propanoate in IUPAC nomenclature. The ester is derived from propanoic acid (with three carbon atoms, hence 'propanoate') and ethanol (containing ethyl as the alkoxy group). The name reflects the acid part first (propanoate) followed by the alcohol derivative (ethyl).

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