alkanes a) 2,2,4-trimethylpentane b) 3,4-diethylheptane c) 3-methylheptane d) 4 … ·...

ALKANES

1. Draw structural formula for:

a) 2,2,4-trimethylpentane b) 3,4-diethylheptane

c) 3-methylheptane d) 4-ethyl-3-methylheptane

e) 3-chloro-2-methylhexane f) 2-chloro-2-methylpentane

g) 4-bromo-5-iodo-2,2,3-trimethylhexane h) 5,6-dichloro-3-ethyl-2,3-dimethyloctane

2. Draw and name 3 isomers of C5H12.

3. Which compound has the higher melting point: propane or pentane? Explain.

4. Name the following:

a)

b)

c)

d)

e)

f)

g)

h)

CH3 C CH CH CH CH3

CH3

CH3

CH3 Br

I

CH3 CH CH2 C CH3

CH3

CH3

CH3

CH3 CH2 CH

CH2CH3

CH CH2 CH2 CH3

CH2 CH3

CH3 CH2 CH2 CH2 CH CH3

CH2CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH3

CH3 CH2 CH3

CH3 CH CH CH2 CH2 CH3

CH3

Cl

CH3 C CH2 CH2 CH3

CH3

Cl

CH3 CH C CH2 CH CH CH2 CH3

CH3 CH3

CH2CH3 Cl

Cl

ALKENES

1. Draw structural formula for the following:

a) 2-methylpropene b) trans-2,3-dibromobut-2-ene

c) cis-hex-3-ene d) 2-ethylpent-1-ene

e) cis-4-chloro-5-methylhex-2-ene f) 4,4-dimethylhex-1-ene

g) trans-3-bromo-2-iodo-4,5,5-trimethylhex-2-ene h) trans-3,4-dichloro-6-ethyl-6,7-dimethyloct-3-

ene

2. a) Draw and name the geometric isomers of C2H2Cl2.

b) Which of the two compounds above has the higher melting point? Explain.


a)

b)

c)

d)

e)

f)

g)

h)

CH3 C

CH3

CH2

C C

CH3

CH3

Br

Br

CH3 CH2 C C

H H

CH2 CH3

CH3 CH2 C CH2 CH2 CH3

CH2

CH3 CH CH C C CH3

CH3

Cl

H H

CH3 C CH2 CH CH2

CH2 CH3

CH3

CH3 C CH C C CH3

CH3CH3

CH3

Br

I

CH3 CH C CH2 C C CH2 CH3

CH3

CH2CH3 Cl

ClCH3

ALKYNES

1. Draw structural formula for the following:

a) 4,5-dimethylhept-2-yne b) 3,3-dimethylbut-1-yne

c) 4-methylpent-2-yne d) 4-ethylhex-2-yne

e) 4-chloro-5-methylhex-2-yne f) 5,5-dimethylhept-1-yne

g) 1-iodo-3,4,4-trimethylpent-1-yne h) 6-ethyl-6,7-dimethyloct-3-yne

2. a) Draw and name the isomers of C4H5Cl.

b) Which of the isomer compounds above has the higher melting point? Explain.


a)

b)

c)

d)

e)

f)

g)

h)

CH3 C C CH CH CH3

CH2 CH3CH3

CH C C CH3

CH3

CH3

CH3 C C CH CH3

CH3

CH3 CH2 CH C C CH3

CH2 CH3

CH3 CH CH C C CH3

Cl

CH3

CH3 C CH2 CH2 C CH

CH2 CH3

CH3

CH3 C CH C C

CH3

CH3 CH3

I

CH3 CH C CH2 C C CH2 CH3

CH3 CH3

CH2CH3

Nomenclature for Alcohols Draw the following molecules: a). 2-chlorobutan-2-ol b) 2-methylheptan-2-ol

c) octane-1,4-diol d) cyclopentanol

e)2,3,4-trichloro-6-methylundecan-1-ol

Name the following structures (left to right, top to bottom):

OH

CH2

CH

CH

Cl

Cl

CH

CH

CH3

CH2

CH2

CH2

CH2

CH2

CH3

Cl

HO

CH2

CH2

CH2

CH

CH2

CH2

CH2

CH3

OH

CH3

CH2 CCH3

Cl

OH

C C C C C C C

C

OH

C

CC

C

C

OH

Nomenclature for Ethers Draw the following molecules: a) 1-chloroethoxypropane b) 2-methyl-1-propoxyoctane

c) propoxypropane d) 2-methoxypropane

e) 7-methyoxyoctan-2 -ol

Name the following structures (from left to right, top to bottom):

CH3

CH2

CH2

O

CH2

CH2

CH3

CH3

CH

CH2

O

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH3

CH3

CH3

CH

CH2

CH2

CH2

CH2

CH

CH3

OH

O

CH3

C C O C C C

Cl

C C

C

O C

Nomenclature for Aldehydes Draw the following molecules: a) 3,3-dimethylbutanal b) 4-bromo-3-chloro-5-ethylheptanal

c) 2-bromo-3-ethylhexanal d) 4-chloropentanal

e) 2,2,4-trichlorooctanal


C C C

CC

Cl

O

CH

C

CH2

CH

CH2

CH2

CH2

CH3

Cl

Cl Cl

O

CH2

CH

CH

CH

CH

CH

CH2

CH3

Cl

Br CH3

O

CH3

CH3

C

CH2CH

O

CH3CH3

C C C C C C

OBr

C

C

Nomenclature for Ketones Draw the following molecules: a) 3-chloro-4-phenylpentan-2-one b) 3-bromohexan-2-one

c) 3-ethyl-2,5,7-trimethyloctan-4-one d) 2,2-dimethyldecan-4-one

e) 1,3,5-trichlorohexane-2,4-dione


CC

CC

CC

O

OCl

Cl

Cl

CH3

C

CH2C

CH2CH2

CH2CH2

CH2CH3

O

CH3

CH3

CH3

CH

CH2 CH

C CH

CH CH3

CH3

CH3

O

CH2CH3

CH3

CH

CH

CH3

CCH3

O

Cl

C C C C C C

O

Br

Nomenclature for Carboxylic Acids Draw the following molecules: a) 3-fluoropentanoic acid b) 2,2-dimethylbutanoic acid

c) 2,3,3,5-tetrachlorooctanoic acid d) 4,4-dimethylhex-2-enoic acid

e) propandioic acid


OH C C C C C C C C

O

Cl

Cl

Cl Cl

C C C C C OH

F

O

OH C C C OH

OO

C C C C OH

C

C

O

C C C C C C OH

OC

C

Nomenclature for Esters Draw the following molecules: a) butyl ethanoate b) 2-butyl propanoate

c) 3-pentyl butan 2-oate d) 3-methylbutyl propanoate

e) dichloromethyl ethanoate


C C C C O C C

O

C C O C

O Cl

Cl

C C C O C C C C

O

C C C O C C

C

C

O

C C C

C

C

O C

O

C C C

C

Nomenclature for Amines Draw the following molecules: a) N-ethylaminopropane b) 2-aminohex-1-ene

c) 4-chloro-2-aminoheptane d) N-ethyl-N-methyl-2-aminobutane

e) N-methylaminomethane


C C C C C C

N

C C N C C C

C N C

C C C C C C C

Cl

N

C C C C

N

C C

C

Nomenclature for Amides Draw the following molecules: a) N-propyl propanamide b) N-bromo-N-methyl hexanamide

c) N,N-dimethyl pentanamide d) 3,N-dimethyl-N-propyl butanamide

e) 2-ethyl-N-methyl butanamide


C C C C C C N C

O

Br

C C C N C C C

O

C C C C C N C

O

C

C C C C N C

O

C

C

C C C C N C C C

O

CC

CH3 CH

Br

CH2 C

O

OH

Name the following compounds:

1. O

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.

14.

15.

16.

17.

CH3 C CH3

CH3

OH

CH3 C CH2 CH3

O

CH3 CH CH2 OH

Cl

CH3 C C CH2 CH

O

CH3 C CH2 CH3

CH3

NH CH3

CH3 C C CH3

Cl Br

CH3 CH CH2 CH CH2 CH3

CH3 CH2 CH2 CH2

CH2CH3

CH3 CH2 C O CH3

O

O

O

CH3 CH2 C N CH2

O

CH3

Cl

CH3 CH2 CH2 CH CH3

O CH2 CH3

CH3 C

O

O CH

CH3

CH2 CH3

O

OH

CH3 CH C C CH2 CH

O

OHCH3

Cl

Draw the following compounds:

1. 1-propoxypentane

2. 3-bromobutan-1-ol

3. butan-2-one

4. 2-chloropropan-1-ol

5. pent-3-enal

6. N-methyl-2-amino-2-methylbutane

7. 2-ethylpentanal

8. 4-ethyl-2-methylnonane

9. 2-methylpropan-2-ol

10. methyl propanoate

11. 3-ethylhexan-2-one

12. cis-2-bromo-3-chlorobut-2-ene

13. N-chloro-N-ethyl propanamide

14. 2-ethoxypentane

15. 2-butyl ethanoate

16. 3-methylhexanoic acid

17. trans-3-chloro-4-hydroxy-5-methylhex-3-enal

Comparing Organic Compounds

Draw the following 5 molecules and place them in order of highest boiling point to lowest

boiling point. Research their boiling points and confirm your answers. Explain your

reasoning fully: a) pentan-1-ol b) 2-methylbutan-2-ol

c) ethoxypropane d) pentan-2-one

e) pentanal

Draw the following 7 molecules and place them in order of highest boiling point to lowest

boiling point. Explain your reasoning: a) hexan-3-ol b) methoxy-2-methylbutane

c) hexanoic acid d) hexan-3-one

e) propyl propanoate f) 2-methylpentane

g) 3-aminohexane

Organic Reactions Worksheet

Note – Use HCl, H2O, (O) such as KMnO4, NH3, and Cl2 when necessary

1. Using an alkene, produce butan-2-one

2. Using two alcohols, produce methyl butanoate

3. Using an alkane and an carboxylic acid, produce N-ethyl butanamide

4. Using an alkane and an alkene, produce methoxyethane

5. Using an alcohol and an alkyl halide, produce ethyl propanoate

6. Using an alcohol, produce an aminoethane

7. Using an alkene, produce pentan-2-one

ALIPHATIC HYDROCARBON ASSIGNMENT

1. (a) Look up the boiling points for the alkanes, methane through decane.

(b) Explain the trend in their boiling points.

2. (a) Lookup the boiling points for 2-methyl pentane and 2,2-dimethyl butane.

(b) Draw their structural formulae.

(c) Name their straight chain alkane isomer.

(d) Explain the trend in boiling points within this series of isomers.

3. Explain why reactions involving alkanes are often quite slow in spite of being

significantly exothermic.

4. Construct models, give structural formulae and condensed formulae and IUPAC names

for as many isomers of C6H12 as possible. Use straight chain branches only.

6. Give structural and projection formulae for the geometric isomers of 3-hexene.

7. Using structural formulae, illustrate the following reactions

(a) propane + chlorine

(b) but-1-yne + oxygen

(c) but-1-ene + hydrochloric acid

SOME FUNCTIONAL GROUPS AND THEIR REACTIVITY

1. List the functional groups for the following classes of compounds; alcohols, ethers

aldahydes, ketones, carboxylic acids, esters, amines and amides.

2. For each of the following sets of compounds and their boiling points

(i) Name the compounds.

(a) CH4 (-164 °C) HCHO (-21 °C) CH3OH (65 °C) HCO2H (101 °C)

(b) CH3OH (65 °C) C2H5OH (79 °C) C3H7OH (98 °C)

(c) C2H6 (-89 °C) CH3OCH3 (-25 °C) C2H5OC2H5 (35 °C)

(d) C3H8 (-42 °C) CH3COCH3 (56 °C) C2H5COC2H5 (102 °C)

(e) CH3CO2H (118 °C) C2H5CO2H (141 °C) C3H7CO2H (164 °C)

(f) CH3CO2CH3 (57 °C) C2H5CO2C2H5 (99 °C)

(ii) Explain the trend in boiling point.

3. Give the structural diagrams, condensed formulae and the names for the primary,

secondary and tertiary isomers of C6H13OH.

4. Using an alcohol with a two carbon main chain, illustrate end explain the differences in

oxidation of primary, secondary and tertiary alcohols. In each case, name the product of

the reaction and use oxidation numbers to confirm that oxidation has occurred.

5. Illustrate using structural formulae and balanced equations, each of the following. Name

all products and types of reaction.

(a) methanoic acid + water

(b) 2-methylbutanoic acid + sodium carbonate

(c) ethanoic acid + propanol

(d) propylethanoate + sulfuric acid

alkanes a) 2,2,4-trimethylpentane b) 3,4-diethylheptane c) 3-methylheptane d) 4 … ·...

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