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Chem 10.3

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Chem 10.3

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> ib-chemistry > hl > questionbank > organic-chemistry-hl >

types-of-organic-reactions
types of organic reactions
Question 0 Non-Calculator
The nitration of benzene is an example of what type of reaction
mechanism?

A. Electrophilic addition

B. Electrophilic substitution

C. Nucleophilic addition

D. Nucleophilic substitution

Question 1 Non-Calculator
What is the structure of the carbocation intermediate in the
nitration of benzene?

A.

B.
C.

D.

Question 2 Non-Calculator
Which of the following is/are the most suitable reagent(s) for the
conversion of butanoic acid to butan-1-ol?

A. LiAlH4
B. H2 with a Ni catalyst
C. Sn and HCl
D. NaBH4

Question 3 Non-Calculator
The first step of a nucleophilic substitution reaction is shown.

Which of the following statements is true?


A. The reaction is a heterolytic fission and the curly arrow
indicates transfer of 1 electron

B. The reaction is a heterolytic fission and the curly arrow


indicates transfer of 2 electrons

C. The reaction is a homolytic fission and the curly arrow


indicates transfer of 1 electron

D. The reaction is a homolytic fission and the curly arrow


indicates transfer of 2 electrons

Question 4 Calculator Allowed


[Maximum mark: 8]

Nitration reactions often involve the formation of the nitronium


+
ion, NO2 . The structure of the nitronium ion is shown.

(a). State the reagents used to generate the nitronium ion. [1]
(b). The formation of the nitronium ion involves the
intermediate X . The Lewis structure of intermediate X is
shown.

Draw two curly arrows to show how the nitronium ion


forms from intermediate X. [1]
(c). The nitronium ion can react with toluene to produce
4-nitrotoluene.
Draw the mechanism of this nitration reaction. [4]
(d). The reduction of 4-nitrotoluene requires two reaction
steps. The product of the first step is compound Y .

Draw the structure of compound Y . [2]

Question 5 Calculator Allowed


[Maximum mark: 6]

Two methods for synthesising 3−hydroxybutanoic acid are shown.

(a). Name a reducing agent that could be used in reaction


1. [1]
(b). Reaction 2 occurs via an SN 2 mechanism. Sodium
hydroxide is used as the nucleophile.
(i). State how the rate of reaction changes if the
concentration of sodium hydroxide is doubled. [1]
(ii). Explain why sodium hydroxide reacts more
rapidly than water in this reaction. [2]
(iii). Reaction 2 can also be performed using a
bromoalkane as the starting material, as shown.
Using the bond energies in section 11 of the data booklet,
explain why the reaction rate is higher if a bromoalkane is
used. [2]

Question 6 Non-Calculator
Which of the following compounds undergoes SN 1 reactions at the
greatest rate?

A.

B.

C.

D.

Question 7 Non-Calculator
Some halogenoalkanes can undergo both SN 1 and SN 2 reactions
with sodium hydroxide.
Which of the following statements are true?

The SN 2 reaction is more strongly favoured in aprotic


I.
polar solvents
II. The SN 2 reaction is stereospecific
The SN 2 reaction rate is proportional to the nucleophile
III.
concentration

A. I and II only

B. I and III only

C. II and III only

D. I, II, and III

Question 8 Non-Calculator
An alkene reacts with the interhalogen compound BrCl.

Identify the major intermediate and product of this reaction.

Intermediate Major product

A.

B.

C.
Intermediate Major product

D.

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