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4. Alkanes and Cycloalkanes

IUPAC Naming

4. Alkanes and Cycloalkanes

IUPAC Naming

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The different parts of an IUPAC name

The different parts of an IUPAC name

Johnny Betancourt

Learning Alkane Prefixes up to 12 Carbons in Length

Learning Alkane Prefixes up to 12 Carbons in Length

Johnny Betancourt

Naming the root chain

Naming the root chain

Johnny Betancourt

How to determine the direction of the root chain

How to determine the direction of the root chain

Johnny Betancourt

Name the longest carbon chain

Name the longest carbon chain

Johnny Betancourt

Name the longest carbon chain

Name the longest carbon chain

Johnny Betancourt

How to identify and locate branches (substituents)

How to identify and locate branches (substituents)

Johnny Betancourt

Name the longest carbon chain and substituents

Name the longest carbon chain and substituents

Johnny Betancourt

Proper name ordering and punctuation

Proper name ordering and punctuation

Johnny Betancourt

Provide the IUPAC name for the following alkane

Provide the IUPAC name for the following alkane

Johnny Betancourt

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Practice this topic

Multiple Choice

What is the IUPAC name of the following molecule?

Textbook Question

Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description. a. an isopropylheptane b. a diethyldecane

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Textbook Question

Draw the structure that corresponds with each name. k. cyclobutylcyclohexane l. cis-1-bromo-3-chlorocyclohexane

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Textbook Question

Draw the structure that corresponds with each name. e. 2,2,4,4-tetramethylhexane f. trans-1,3-diethylcyclopentane

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Textbook Question

1. Without looking at the structures, give molecular formulas for the compounds in Problem-3-8 (a) and (b). (a) 4-(1,1-dimethylethyl)octane (b) 5-(1,2,2-trimethylpropyl)nonane 2. Use the names of the groups to determine the number of carbon atoms; then use the (2n+2) rule.

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Textbook Question

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly. a. 2-ethylpentane b. 3-isopropylhexane

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Textbook Question

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly. a. 3-ethyl-4-methylpentane b. 2-ethyl-3-methylpentane c. 3-dimethylhexane

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Textbook Question

Give structures and names for a. the five isomers of C6H14

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Textbook Question

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order. a. CH3CH(CH2CH3)CH2CH3

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Textbook Question

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly. a. 2-ethylpentane b. 3-isopropylhexane

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Textbook Question

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly. a. 3-ethyl-4-methylpentane b. 2-ethyl-3-methylpentane c. 3-dimethylhexane

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Textbook Question

Draw the structure and give the molecular formula for each of the following compounds. a. 1-ethyl-3-methylcycloheptane b. isobutylcyclohexane

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Textbook Question

Draw the structures of the following compounds. a. 4-(1,1-dimethylethyl)octane

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Textbook Question

Write structures for the following compounds. a. 3-ethyl-4-methylhexane b. 3-ethyl-5-isobutyl-3-methylnonane c. 4-tert-butyl-2-methylheptane d. 5-isopropyl-3,3,4-trimethyloctane

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Textbook Question

Which of the following structures represent the same compound? Which ones represent different compounds? a. <

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Textbook Question

Provide IUPAC names for the following compounds. a. (CH3)2CHCH2CH3 b. CH3—C(CH3)2—CH3 c.

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Textbook Question

Give the IUPAC names of the following alkanes. a. CH3C(CH3)2CH(CH2CH3)CH2CH2CH(CH3)2 b.

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Textbook Question

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order. c. d.

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Textbook Question

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly. e. 2-cyclohexylbutane f. 2,3-diethylcyclopentane

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Textbook Question

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly. c. 5-chloro-4-methylhexane d. 2-dimethylbutane

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Textbook Question

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly. d. 4-isobutylheptane e. 2-bromo-3-ethylbutane f. 2,3-diethyl-5-isopropylheptane

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Textbook Question

Draw the structure and give the molecular formula for each of the following compounds. e. 3-ethyl-2,4-dimethylhexane f. 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane

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Textbook Question

Draw the structure and give the molecular formula for each of the following compounds. c. cyclopropylcyclopentane d. 3-ethyl-1,1-dimethylcyclohexane

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Textbook Question

Draw the structures of the following compounds. c. 3,3-diethyl-4-(2,2-dimethylpropyl)octane

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Textbook Question

Draw the structures of the following compounds. b. 5-(1,2,2-trimethylpropyl)nonane

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Textbook Question

Provide IUPAC names for the following compounds. d. e. f.

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Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed. h. 5-ethyl-2-methylhexane

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Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed. g. 3,3-dichlorooctane

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Textbook Question

Draw skeletal structures for the following: b. 1,3-dimethylcyclohexane

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Textbook Question

Draw skeletal structures for the following: a. 5-ethyl-2-methyloctane

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Textbook Question

Draw skeletal structures for the following: d. propylcyclopentane

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Textbook Question

Draw skeletal structures for the following: c. 2,3,3,4-tetramethylheptane

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Textbook Question

Draw a condensed structure and a skeletal structure for each of the following: l. 5-isopropyldecane

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Textbook Question

Draw a condensed structure and a skeletal structure for each of the following: k. 3,4-dimethyloctane

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Textbook Question

What is each compound's systematic name? h.

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Textbook Question

What is each compound's systematic name? g. CH3CH2C(CH2CH3)2CH2CH2CH3

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Textbook Question

Draw skeletal structures for the following: f. 2,6-dimethyl-4-(2-methylpropyl)decane

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Textbook Question

Draw skeletal structures for the following: e. 2-methyl-4-(1-methylethyl)octane

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Textbook Question

Give the systematic names for all alkanes with molecular formula C7H16 that do not have any secondary hydrogens.

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Textbook Question

What is each compound's systematic name? g.

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Textbook Question

Draw the structure for each of the following: (e) 2,5-dimethyl-4-(2-methylpropyl)octane

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Textbook Question

Draw the structure for each of the following: (d) 2,4,5-trimethyl-4-(1-methylethyl)heptane

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Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed. l. 2-methyl-N,N-dimethyl-4-hexanamine

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Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed. k. 2-methyl-2-isopropylheptane

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Textbook Question

Draw a condensed structure and a skeletal structure for each of the following: g. 4-(1,1-dimethylethyl)heptane

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Textbook Question

What is each compound's systematic name? e.

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Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.] (e) 2,6-diethyl-1-methylcycloheptane

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Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.] (c) 6-ethyl-3-methyloctane

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Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.] (d) 4-butyldecane

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Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.] (b) 1,5-dimethylcyclohexane

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Textbook Question

Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.] (k) rule 6

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Textbook Question

Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.] (n) rule 7

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Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.] (a) 4-methylhexane

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Textbook Question

What is each compound's systematic name? c.

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Textbook Question

What is each compound's systematic name? d.

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Textbook Question

Draw the structure for each of the following: (b) 2,2-dimethyl-4-isopropyloctane

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Textbook Question

Draw the structure for each of the following: (c) 4,4-diethyldecane

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Textbook Question

What is each compound's systematic name? e.

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Textbook Question

What is each compound's systematic name? b.

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Textbook Question

Draw the structure for each of the following: (a) 2,2-dimethyl-4-isopropyloctane

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Textbook Question

Draw the structure that corresponds with each name. a. 3-ethyloctane b. 4-isopropyldecane

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Textbook Question

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°). a. butane b. isobutane

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Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°). a. CH3CH2CH(CH3)2 b. (CH3)3CCH2CH3

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Textbook Question

a. How many alkenes could you treat with H2, Pd/C to prepare methylcyclopentane? b. Which of the alkenes is the most stable? c. Which of the alkenes has the smallest heat of hydrogenation?

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Textbook Question

What alkene would you start with if you wanted to synthesize b. ethylcyclopentane?

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Textbook Question

What reagents would you use for the following syntheses? b. (E)-3-hexene from 3-hexyne

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Textbook Question

What reagents would you use for the following syntheses? a. (Z)-3-hexene from 3-hexyne

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Textbook Question

Describe the alkyne you should start with and the reagents you should use if you want to synthesize b. cis-2-butene.

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Textbook Question

Describe the alkyne you should start with and the reagents you should use if you want to synthesize a. pentane.

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Textbook Question

What is the product of each of the following reactions? b.

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Textbook Question

What new products are obtained from metathesis of the following alkyne?

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Textbook Question

What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.) a.

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Textbook Question

What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis? a.

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Textbook Question

What compound undergoes metathesis to form each of the following compounds? a.

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Textbook Question

What products are obtained from metathesis of each of the following alkenes? a. CH3CH2CH=CH2

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Textbook Question

What products are obtained from metathesis of each of the following alkenes? b.

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Textbook Question

Draw the product of ring-closing metathesis for each of the following compounds: a.

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Textbook Question

Draw the structure for each of the following: (f) 4-(1,1-dimethylethyl)octane

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Textbook Question

b. Give each isomer its systematic name.

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Textbook Question

f. Which isomers contain a tert-butyl group?

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Textbook Question

d. Which isomers contain an isopropyl group?

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Textbook Question

Draw the structure and give the systematic name for a compound with molecular formula C5H12 that has (c) one tertiary hydrogen

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Textbook Question

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review. (a)

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Textbook Question

Predict the product of the following reactions. (b)

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Textbook Question

Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.]

(j) rule 5

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(LOOKING AHEAD) In Section 3.3.3, we explain that a 1° carbon is attached to one carbon, a 2° to two, a 3° to three, and a 4° to four. Label each of the carbons in 4-ethyl-1,1-dimethylcycloheptane as 1° , 2°, 3°, or 4°.

<IMAGE>

4 - ethyl - 1, 1 - dimethylcycloheptane

Textbook Question

Draw the structures of octane and isooctane.

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Textbook Question

Give each substituent on the ten-carbon chain a common name and a parenthetical name

c. <IMAGE>

d. <IMAGE>

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Textbook Question

What is each compound’s systematic name?

i. <IMAGE>

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Textbook Question

What is each compound’s systematic name?

e. <IMAGE>

f. <IMAGE>

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Textbook Question

c. How many isomers have common names?

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