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Draw all the isomers that have molecular formula C5H12Br. (Hint: There are eight.)

a. Give the systematic name for each of the isomers.

b. Give a common name for each isomer that has a common name.

c. How many of the isomers are primary alkyl halides?

d. How many of the isomers are secondary alkyl halides?

e. How many of the isomers are tertiary alkyl halides?

Short Answer

Expert verified

Here, four isomers are primary halides, three isomers are secondary alkyl halides and one isomer is a tertiary alkyl halide.

Step by step solution

01

Definition of isomers and primary, secondary, and tertiary alkyl halides.

Isomers are compounds that have the same number of atoms, i.e., the same empirical formula but differ in the way the atoms are organized.

A halogen is connected to a primary carbon in a primary alkyl halide.

A halogen is bonded to a secondary carbon in a secondary alkyl halide.

A halogen is connected to a tertiary carbon in a tertiary alkyl halide.

02

Rules for finding the systematic names and common names of halide.

For systematic names, Alkyl halides are classified as substituted alkanes in the IUPAC system. The halogen prefixes all end in "o." (that is, fluoro, chloro, bromo, and iodo). As a result, alkyl halides are often referred to as haloalkanes.

For common names, the name of the alkyl group is followed by the name of the halogen, with the "ine" ending of the halogen name (fluorine, chlorine, bromine, and iodine) substituted by "ide" in the common names (fluoride, chloride, bromide, and iodide).

03

The systematic name for each of the isomers.

04

The common name for each of the isomers that has a common name.

The rest do not have a common name.

05

The number of isomers that are primary alkyl halides.

There are four isomers that are primary alkyl halide.

06

The number of isomers that are secondary alkyl halides.

There are three isomers that are secondary alkyl halide as shown below.

07

The number of isomers that are tertiary alkyl halides.

There is one isomer that is tertiary alkyl halide as shown below.

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Most popular questions from this chapter

a. Draw a potential energy diagram for rotation about the C-C bond of 1,2-dichloroethane through 360degree, starting with the least stable conformer. The anti-conformer is 1.2 kcal/mol more stable than a gauche conformer. A gauche conformer has two energy barriers, 5.2 kcal/mol and 9.3 kcal/mol.

b. Draw the conformer that is present in greatest concentration.

c. How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?

d. How much more stable is the most stable staggered conformer than the least stable eclipsed conformer?

Draw the most stable conformer of the following molecule. (A solid wedge points out of the plane of the paper toward the viewer. A hatched wedge points back from the plane of the paper away from the viewer.)

Which has

a. the higher boiling point: 1-bromopentane or 1-bromohexane?

b. the higher boiling point: pentyl chloride or isopentyl chloride?

c. the greater solubility in water: 1-butanol or 1-pentanol?

d. the higher boiling point: 1-hexanol or 1-methoxypentane?

e. the higher melting point: hexane or isohexane?

f. the higher boiling point: 1-chloropentane or 1-pentanol?

g. the higher boiling point: 1-bromopentane or 1-chloropentane?

h. the higher boiling point: diethyl ether or butyl alcohol?

i. the greater density: heptane or octane?

j. the higher boiling point: isopentyl alcohol or isopentylamine?

k. the higher boiling point: hexylamine or dipropylamine?

Assign two names for each of the following alkyl halides and indicate whether each is primary, secondary, or tertiary:

Draw the structure for each of the following:

a. 2,2-dimethyl-4-isopropyloctane

b. 2,3-dimethylhexane

c. 4,4-diethyldecane

d. 2,4,5-trimethyl-4-(1-methylethyl) heptane

e. 2,5-dimethyl-4-(2-methylpropyl) octane

f. 4-(1,1-dimethylethyl) octane

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