Hexane, CH3(CH2)4CH3, reacts with Cl2(g) in the presence of ultraviolet light to produce different organic products, including those shown in Table 5.1.
Complete Table 5.1.
structure of product
systematic name of product
CH3(CH2)5Cl
CH3(CH2)3CHClCH3
CH3(CH2)3CHClCH2Cl
1,2-dichlorohexane
CH3(CH2)10CH3
dodecane
CH3(CH2)3CH(CH3)CH(CH3)(CH2)3CH3
5,6-dimethyldecane
5(b)(i)Organic Reaction Types MechanismsEasy1 mark
The mechanism for the reaction of hexane with Cl2(g) involves three stages: stage 1 initiation, stage 2 propagation, stage 3 termination. In stage 1 and 2, free radicals are produced. Describe what is meant by free radical.
Answer
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5(b)(ii)Organic Reaction Types MechanismsEasy1 mark
Name the type of bond breaking that occurs to produce the free radical •Cl from Cl2.
5(b)(iii)AlkanesMedium2 marks
Suggest a reaction sequence of two propagation reactions that result in CH3(CH2)4CH3 forming CH3(CH2)3CHClCH3.
Suggest a reaction sequence of one propagation reaction followed by a termination reaction that results in CH3(CH2)4CH3 forming CH3(CH2)10CH3.
Propagation reaction: CH3(CH2)4CH3→ ...
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Termination reaction: ... → CH3(CH2)10CH3
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5(c)AlkanesEasy1 mark
The proportion of each product varies depending on the type of free radical intermediate that is produced.
Table 5.2
primary free radical
secondary free radical
tertiary free radical
∙C(CH3)H2
∙C(CH3)2H
∙C(CH3)3
(The table shows increasing stability of the radical from primary, through secondary, to tertiary.) Use Table 5.2 to suggest which factor determines the increased stability of free radicals from primary to secondary to tertiary.