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CHM 096

TUTORIAL 5

Feb 2013

(Alcohols, Aldehydes, Haloalkanes, Carboxylic Acids)


1.

What is the molecular formula for the compound: 2,3-dimethyl-1-pentanol?


A.
B.
C.
D.

2.

3.

C5H10O
C7H15O
C5H9O
C7H16O

Give the IUPAC name for the following alkyl halides:


a)

CH3CHCH2CH3

Br

b)

CH3CHCH2CHCH3

CH2Br Br

c)

CH2CHCH2CH2

Br Br
Cl

Draw the structural and skeletal formulas for:


a)
b)
c)

2,2,3-trifluorohexane
2-chloro-3-methylhexane
3-ethyl-4-methyl-2-hexanol

4.

What is the name and structural formula for the alkyl halide produced from the reaction between
propene and hydrogen iodide? Write equation for the reaction.

5.

Write an equation for the conversion of ethane to bromoethane (ethyl bromide).

6.

What is the preferred product when the following haloalkanes react with an ethanolic solution of KOH?
a)
b)

7.

1-bromobutane
2-chloro- 3-methylpentane

Give the formulas and name the alkoxide ions formed when sodium (Na) reacts with:
a)
b)

Methanol
Ethanol

8.

A compound is wrongly named as 3,4-dimethyl-5-pentanol. What should be its correct name?

9.

What are the major and minor products of the following addition reaction?
CH3C(CH3) CH2 + HBr

10.

Which of the following molecules is a tertiary alkyl halide?


A.
B.
C.
D.

1-chloropropane
2-chloro-2-methylpropane
2-chloro-3-methylbutane
trichloromethane

11.

12.

Identify the compounds X and Y in the following substitution reactions. Name the nucleophile in each
reaction.
a)

CH3CH2CH2Cl + NaCN

b)

CH3CHBrCH2CH3 + NaOH

14.

15.

Y + NaBr

What are the reagents used for the conversion of 3-iodo-2-methylpentane to the following compounds?
a)
b)

13.

X + NaCl

2-methyl-2-pentene
2-methyl-3-pentanol

Alkyl halides can undergo both substitution and elimination reactions. Identify the following reactions as
substitution or elimination.
a)

CH3CH2CHCH3 + CN CH3CH2CHCH3 + Br
|
|
Br
CN

b)

CH3CH2CHCH3
|
Br

CH3CH CHCH3 + HBr

a)

Write the condensed structural formulas, and give the names of the first five straight-chained
members of the alcohol homologous series.

b)

Write the condensed structural formula for a tertiary alcohol which has the molecular formula
C5H12O. Name the alcohol.

Give the systematic names for the following compounds and classify them as primary, secondary or
tertiary alcohol.
a)

CH3CHCH2CH2CH2CH3

OH

b)

CH3CH2CH2CH2OH

c)

CH3CH2CHCH2CHCH3

OH
CH3

16.

2-propanol can be prepared by the hydration of an alkene. Name the alkene and write an equation for
the hydration reaction.

17.

Describe one chemical test which may be used to distinguish between 1-butanol and 2-butanol?

18.

What alcohol, on dehydration, would yield?


a)
b)

19.

CH3CH2CH CH2
CH3CH C(CH3)CH2CH3

Write equations for the following reactions:


a)
b)
c)
d)

Complete combustion of propanol in air


Oxidation of methanol by acidified potassium dichromate
Dehydration of ethanol by concentrated sulphuric acid
Esterification of ethanol with propanoic acid

Prepared by: Ho Chong Yuen

20.

21.

Suggest a method or reaction that can be used to:


a)
b)

produce the ester, methyl butanoate, CH3CH2CH2COOCH3, from methanol


convert 1-propanol to propene

a)

What reactions occur when 3-methyl-2-butanol is added to acidified KMnO 4? Describe any
observable changes.
How would you differentiate between a primary alcohol and a tertiary alcohol?

b)
22.

When 1-propanol is heated with acetic acid (ethanoic acid, CH 3COOH) in the presence of concentrated
H2SO4, a compound with a fruity odour is produced. What is the identity of the compound? What type of
reaction has taken place?

23.

Which of the following alcohols is/are stable towards oxidation?


A.
B.
C.

24.

(CH3)2C(OH)CH2CH3
CH3CH2CH(OH)CH3
CH3CH2CH(CH3)CH2OH

Consider the following reactions involving 2-butanol.


A

KOH(aq)
reflux

KMnO4/H+
2-butanol

B
heat

conc. H2SO4
heat
C + D (major product)
a)
b)
c)
d)
25.

Suggest one possible compound for A.


Draw the structural formula for B.
Draw the structural formulas and give the names of C and D (major product).
Give the names of the three types of reactions involved.

Which of the following compounds has a carbonyl functional group?


CH3OCH3

26.

27.

CH3CH2COCH2CH(OH)CH3

Classify the following as aldehyde or ketone.


a)
b)

CH3CH2CHO
HCHO

a)
b)

Write the structural formulas for 3,3-dimethylbutanone


What is the IUPAC name for the compound?

H H
H H
|
|
|
|
H C C C C O
|
|
H
H
H C H
|
H
Prepared by: Ho Chong Yuen

28.

Name the aldehyde obtained from the oxidation of the primary alcohol, 1-octanol.

29.

Name the ketone obtained from the oxidation of the secondary alcohol 2-methyl-3-pentanol.

30.

Write an equation to show the oxidation of pentanal to pentanoic acid. Name the reagent used.

31.

Name the product formed when the following are reduced with lithium aluminium hydride, LiAlH 4.
a)
b)

32.

Butanal
Butanone

Which of the following compounds is expected to be soluble in water, and the solution turns blue litmus
paper red?
CH3CH3

33.

CH3CH2COOH

Write the structural formulas for:


a)
b)
c)
d)

34.

CH3CH2OH

Butanoic acid (C4H8O2)


Ethyl methanoate (C3H6O2)
Sodium propanoate (C3H5O2Na)
Sodium pentoxide (C5H11ONa)

State whether each of the following statements is true or false.


The process of esterification:
A. requires the use of an acid as a catalyst.
B. is a reversible reaction.
C. is a substitution reaction.

35.

Name the carboxylic acid that, when reacts with ethanol, will give the ester, ethyl propanoate. Write an
equation to represent the esterification reaction.

36.

Raspberry oil contains an ester that can be made by reaction of formic acid, HCOOH with 2-methyl-1propanol. (CH3)2CHCH2OH. What is its structure?

37.

Complete the following equations:

38

a)

CH3COOH + KOH ____________ + __________

b)

HCOOH + _____________ HCOOC3H7 + H2O

c)

C2H5COOH + NaHCO3 __________ + ______ + _______

d)

_____________ + NaOH C2H5OH + C3H7COONa

(acid-catalysed)

Identify the organic compounds P, Q, R, S, and T in the following sequence of reactions.


CH3

CH3CHCH2Cl + Mg

Prepared by: Ho Chong Yuen

dry ether
P

+ CH3CHO

H2O/H+
Q

R
conc. H2SO4

S
Pt

S + H2

39.

a)
b)

40.

What chemical test would you use to distinguish between butanal and butanone?

41.

How would you perform the following conversions?


a)
b)

How would you prepare propanoic acid from propanal?


How would you prepare ethylpentanoate from ethanol?

butanone to 2-fluorobutane.
3-chloro-2-methylpentane to 2-methyl-3-pentanone.

Prepared by: Ho Chong Yuen