Problem Set 2: Hydrocarbons and Functional groups ANSWER KEY

Chemistry 260 Organic Chemistry

1. Which of the following statements about ethane is true?

(1) the hybridization about carbon is sp²

(2) combustion of ethane is endothermic
(3) ethane is a polar molecule
(4) ethane is insoluble in water
(5) ethane is a liquid at STP

The answer is 4.

2. The general formula for an alkane is:

(1) CnH2n+4 (2) CnH2n+2 (3) CnH2n (4) CnH2n-2 (5) CnH2n-4

The answer is 2.

3. Name the following compound by the IUPAC system: C(CH2CH2CH3)4.

(1) tetrapropylmethane (2) 4,4-dipropylheptane

(3) 1,1-dipropylheptane

The answer is 2.
The structure of C(CH2CH2CH3)4 is:

CH2CH2CH3
CH3CH2CH2 C CH2CH2CH3
1 2 3 4
CH2CH2CH3
5 6 7
The IUPAC name: 4,4-dipropylheptane

4. Which of the following is not 3,3-diethylpentane?

(1) C(CH2CH3)4 (2) (3)

CH2CH3 C 2H 5

CH3CH2CCH2CH3 C
H 5C 2
C 2H 5
CH2CH3 H 5C 2

(4) CH3CH2C(CH2CH3)2CH2CH3 (5) none of these

The answer is 5.

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All of the structures in choices (1)-(4) represent 3,3-diethylpentane:
CH2CH3
1 2 3 4 5
CH3CH2CCH2CH3

CH2CH3

5. Give the structural formula of:

(a) 2,2,3,3-tetramethylpentane
(b) 2,3-dimethylbutane
(c) 3,4-dimethyl-4-ethylheptane

(a) CH3 CH3

CH3C CCH2CH3
CH3 CH3
(b) CH3
CH3CHCHCH3
CH3
(c) CH3 CH3
CH3CH2CH CCH2CH2CH3
CH2CH3

6. Give the IUPAC name of:

(a) (CH3)2CHCH2CH2CH3
(b) (C2H5)2C(CH3)CH2CH3
(c)
CH3CH2CHCH2CHCH2CH3
CH3 CH2CH2CH3

(a) 2-methylpentane (b) 3-ethyl-3-methylpentane

CH3
CH3 1 2 3 4 5
CH3CH2CCH2CH3
CH3CHCH2CH2CH3
1 2 3 4 5 CH2CH3

(c) 5-ethyl-3-methyloctane
1 2 3 4 5
CH3CH2CHCH2CHCH2CH3
CH3 CH2CH2CH3
6 7 8

2
(numbering from other end gives 4-ethyl-6-methyloctane. Numbers of alkyl
substituents are higher ⇒ not the best answer.)

7. Which of the following formulae represents the primary alcohol?

(1) RCH2OH (2) RCOOH (3) R2CHOH (4) RCO2R (5) R3COH

The answer is 1.

(1) primary alcohol

(2) carboxylic acid
(3) secondary alcohol
(4) ester
(5) tertiary alcohol

8. How many constitutional isomers are there with the formula C4H10O?

The answer is 7:

CH3CH2CH2CH2OH CH3
CH3CH2CHCH3 H3C C OH
OH CH3
CH3OCH2CH2CH3
CH3CHCH2OH CH3CHOCH3
CH3CH2OCH2CH3 CH3 CH3

9. Name the following compounds:

(a)
CH3CHCH2CH2OH
Cl
3-chloro-1-butanol (d)
Cl CH2CH2CH2CH CH2
5-chloro-1-pentene
(b)
CH3CH2CH(OH)CH3 (e)
2-butanol OH
CH3 C C 2H 5
CH3
2-methyl-2-butanol

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 (c) (f)
CH3

CH3CHCH2CH2CH2Cl H3C CH C C CH2

H
CH3 CH2 Br
CH3
3-bromo-3,4-dimethyl-1-hexene
1-chloro-4-methylpentane

10. Draw the structures of all possible constitutional isomers of:

(a) C4H9Cl (b) C3H6Cl2 (c) C3H8O

(a) First, go through all the possible functional groups and determine which
ones have molecules of formula C4H9Cl.

Chloroalkane?
An alkane has general formula CnH2n+2. Replace one H with Cl, get CnH2n+1Cl.
For C4, formula is C4H9Cl. Matches formula given in question ⇒ chloroalkane
is a possible structure. ü

Chloroalkene?
An alkene has general formula CnH2n. Replace one H with Cl, get CnH2n-1Cl.
For C4, formula is C4H7Cl. Does not match formula given in question ⇒
chloroalkene is not a possible structure. X

Chloroalkyne?
An alkyne has general formula CnH2n-2. Replace one H with Cl, get CnH2n-3Cl.
For C4, formula is C4H5Cl. Does not match formula given in question ⇒
chloroalkyne is not a possible structure. X

Chlorocycloalkane?
A cycloalkane has general formula CnH2n. Replace one H with Cl, get CnH2n-
1Cl. For C4, formula is C4H7Cl. Does not match formula given in question ⇒
chlorocycloalkane is not a possible structure. X

Chlorocycloalkene? X
Chlorocycloalkyne? X

The structures are then all the possible chloroalkanes we can draw of
formula C4H9Cl:

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 Cl
CH3CH2CH2CH2Cl CH3CH2CHCH3
1-chlorobutane 2-chlorobutane

CH3 CH3
CH3CHCH2Cl H3C C CH3
Cl
1-chloro-2-methylpropane 2-chloro-2-methylpropane

(b) First, go through all the possible functional groups and determine which
ones have molecules of formula C3H6Cl2.

Dichloroalkane?
An alkane has general formula CnH2n+2. Replace two H with Cl, get CnH2nCl2.
For C3, formula is C3H6Cl2. Matches formula given in question ⇒
dichloroalkane is a possible structure. ü

Dichloroalkene?
An alkene has general formula CnH2n. Replace two H with Cl, get CnH2n-2Cl2.
For C3, formula
is C3H4Cl2. Does not match formula given in question ⇒ dichloroalkene is
not a possible structure. X

Dichloroalkyne?
An alkyne has general formula CnH2n-2. Replace two H with Cl, get CnH2n-4Cl.
For C3, formula
is C3H2Cl2. Does not match formula given in question ⇒ dichloroalkyne is
not a possible structure. X

Dichlorocycloalkane?
A cycloalkane has general formula CnH2n. Replace two H with Cl, get CnH2n-
2Cl2. For C3, formula is C3H4Cl2. Does not match formula given in question ⇒
dichlorocycloalkane is not a possible structure. X

Dichlorocycloalkene? X
Dichlorocycloalkyne? X

The structures are then all the possible dichloroalkanes we can draw of
formula C3H6Cl2:

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 Cl
ClCH2CH2CH2Cl CH3CH2CHCl
1,3-dichloropropane 1,1-dichloropropane

Cl Cl
CH3CHCH2Cl H3C C CH3
Cl
1,2-dichloropropane 2,2-dichloropropane

(c) First, go through all the possible functional groups and determine which
ones have molecules of formula C3H8O.

Alcohol?
An alcohol with an alkane backbone has general formula CnH2n+2O. For C3,
formula is C3H8O. Matches formula given in question ⇒ alcohol with alkane
backbone is a possible structure. ü
Alcohol with an alkene backbone has general formula CnH2nO. X
Alcohol with an alkyne backbone has general formula CnH2n-2O. X
Alcohol with a cycloalkane backbone has general formula CnH2nO. X

Ether?
An ether with an alkane backbone has general formula CnH2n+2O. For C3,
formula is C3H8O. Matches formula given in question ⇒ ether with alkane
backbone is a possible structure. ü
Ether with an alkene backbone has general formula CnH2nO. X
Ether with an alkyne backbone has general formula CnH2n-2O. X
Ether with a cycloalkane backbone has general formula CnH2nO. X

Aldehyde?
An aldehyde with an alkane backbone has general formula CnH2nO. For C3,
formula is C3H6O. Does not match formula given in question ⇒ aldehyde
with alkane backbone is not a possible structure. X

Aldehyde with alkene backbone has general formula CnH2n-2O. X

Aldehyde with alkyne backbone has general formula CnH2n-4O. X
Adehyde with cycloalkane backbone has general formula CnH2n-2O. X

Carboxylic acid?
No, because two O atoms in carboxylic acid. X

Ester?
No, because two O atoms in ester. X

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 The structures are then all the possible alcohols and ethers with alkane
backbones (i.e. all saturated C-C bonds) of formula C3H8O:

OH
CH3CH2CH2OH CH3CHCH3
propanol 2-propanol

CH3CH2OCH3
ethyl methyl ether

11. Elemental combustion analysis of an alcohol gave the following results:

Carbon 68.13%, Hydrogen 13.72%. Possible structures for this alcohol are

(1) 3-methyl-2-butanol
(2) 2-methyl-3-pentanol
(3) 2-pentanol
(4) 2-methylcyclohexanol
(5) none of the above

The answers are 1 and 3.

Assume we have 100 g of the compound:

C 68.13% 68.13 g / 12.01 g mol-1 = 5.67 mol
H 13.72% 13.72 g / 1.008 g mol-1 = 13.6 mol
O 18.15% 18.15 g / 16.00 g mol-1 = 1.13 mol

Note: the amount of O is found by difference. An alcohol has the general

formula ROH where R = alkyl. Dividing by 1.13 mol and rounding to the
nearest whole number gives: C: 5; H: 12; O: 1

Therefore, C5H12O is the simplest formula. The possible structures are:

(1) 3-methyl-2-butanol (3) 2-pentanol

OH OH
CH3CHCHCH3 CH3CHCH2CH2CH3
CH3

Both fit the simplest formula.

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12. Josamycin is a macrolide antibiotic produced by the bacteria, Streptomyces
narbonensis. This compound has antimicrobial activity against a wide
spectrum of pathogens. Write the name of each of the circled functional
groups on the lines provided below.

Answers: 1 ester or carboxylic ester, 2 amine, 3 aldehyde, 4 ether, 5 alcohol

13. Write the name of each indicated functional group in the space provided.

Answers: (1) ester, (2) carboxylic acid, (3) amine, (4) amide.

14. Draw all constitutional isomers with the molecular formula C5H11Cl. Draw
each structure only once.