(c) doc b(c) doc bDoc Brown's Chemistry  Revising Advanced Level Organic Chemistry

Revision Notes PART 3 HALOGENOALKANES (haloalkanes, alkyl halides)

3.1 The molecular structure and naming-nomenclature of halogenoalkanes once known as 'haloalkanes' ('alkyl halides') - 3.1.2 More examples of HALOGENOALKANES (of four carbons i.e. C4 molecules)

This page describes the molecular structure and naming of C4 halogenoalkanes e.g. 1-bromobutane, 2-chloro-2-methylpropqane of four carbon atoms etc. Examples of displayed formula of halogenoalkane molecules (fluoro, chloro, bromo and iodo alkane derivatives), graphic formula, molecular formula, skeletal formula, structural formula. Some 'old' trivial and commercial names are quoted in () though their use should be avoided if possible.

See also 3.1.1 haloalkanesC1-C3 * 3.1.3 more haloalkanes >C4_and cyclohaloalkanes

1. The molecular formula (c) doc b, where X = halogen, allows 4 isomers, 2 based on butane and 2 based on 2-methylpropane.

(a) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 1-chlorobutane (butyl chloride)

(b) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 2-chlorobutane

(c) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 1-chloro-2-methylpropane

(d) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 2-chloro-2-methylpropane (tert- or t-butyl chloride)


2. (c) doc bproduces 9 isomers when the two halogen atoms are the same, 6 based on butane and 3 based on 2-methylpropane.

(a) (c) doc b, (c) doc b, (c) doc b, 1,1-dichlorobutane

(b) (c) doc b, (c) doc b, (c) doc b, 1,2-dichlorobutane

(c) (c) doc b, (c) doc b, (c) doc b, 1,3-dichlorobutane

(d) (c) doc b, (c) doc b, (c) doc b, 1,4-dichlorobutane

(e) (c) doc b, (c) doc b, (c) doc b, 2,2-dichlorobutane

(f) (c) doc b, (c) doc b, (c) doc b, 2,3-dichlorobutane

(g) (c) doc b, (c) doc b, (c) doc b, 1,1-dichloro-2-methylpropane

(h) (c) doc b, (c) doc b, (c) doc b, 1,2-dichloro-2-methylpropane

(i) (c) doc b, (c) doc b, (c) doc b, 1,3-dichloro-2-methylpropane

3. There are 8 isomers of the formula (c) doc bbased on butane

(a) 1-bromo-1-chlorobutane, (c) doc b, (c) doc b

(b) 1-bromo-2-chlorobutane, (c) doc b, (c) doc b

(c) 1-bromo-3-chlorobutane, (c) doc b, (c) doc b

(d) 1-bromo-4-chlorobutane, (c) doc b, (c) doc b

(e) 2-bromo-1-chlorobutane, (c) doc b, (c) doc b

(f) 2-bromo-2-chlorobutane, (c) doc b, (c) doc b

(g) 2-bromo-3-chlorobutane, (c) doc b, (c) doc b

(h) 3-bromo-1-chlorobutane, (c) doc b, (c) doc b


4. Other bromo-chloro alkanes based on propane or butane involving bromo, chloro and methyl substituent include

(a) 1,2-dibromo-1-chlorobutane, C4H7Br2Cl, (c) doc b, (c) doc b

(b) 1,2-dibromo-2-chlorobutane, (c) doc b, (c) doc b

(c) 1,2-dibromo-3-chlorobutane, (c) doc b, (c) doc b

(d) 1,2-dibromo-4-chlorobutane, (c) doc b, (c) doc b

(e) 1,3-dibromo-1-chlorobutane, (c) doc b, (c) doc b

(f) 1,3-dibromo-2-chlorobutane, (c) doc b, (c) doc b

(g) 1,3-dibromo-3-chlorobutane, (c) doc b, (c) doc b

(h) 1,3-dibromo-4-chlorobutane, (c) doc b, (c) doc b

(i) 1,4-dibromo-1-chlorobutane, (c) doc b, (c) doc b

(j) 1-bromo-1,2-dichlorobutane, C4H7BrCl2, (c) doc b, (c) doc b

(k) 1-bromo-1-chloro-2-methylpropane, C4H8BrCl, (c) doc b, (c) doc b

(l) 1-bromo-2-chloro-2-methylpropane, (c) doc b, (c) doc b

(m) 1-bromo-3-chloro-2-methylpropane, (c) doc b, (c) doc b

(n) 2-bromo-1-chloro-2-methylpropane, (c) doc b, (c) doc b

(o) 2-bromo-1,2-dichlorobutane, C4H7BrCl2, (c) doc b, (c) doc b

(p) 2-bromo-1,3-dichlorobutane, (c) doc b, (c) doc b

(q) 2-bromo-1,4-dichlorobutane, (c) doc b, (c) doc b

(r) 2-bromo-2,3-dichlorobutane, (c) doc b, (c) doc b

(s) 3-bromo-2,2-dichlorobutane, (c) doc b, (c) doc b

See also 3.1.1 haloalkanesC1-C3 * 3.1.3 more haloalkanes >C4_and cyclohaloalkanes

Revision notes for GCE Advanced Subsidiary Level AS Advanced Level A2 IB Revise AQA GCE Chemistry OCR GCE Chemistry Edexcel GCE Chemistry Salters Chemistry CIE Chemistry, WJEC GCE AS A2 Chemistry, CCEA/CEA GCE AS A2 Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and AP Honours/honors level courses) Formulae keywords: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism C4H9Cl CH3CH2CH2CH2Cl C4H8Cl2 C4H8BrCl C4H7Br2Cl C4H7BrCl2 C4H8BrCl

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