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ORGANIC MIDTERM EXAM

Total questions: 83

Worksheet time: 43mins

Name
Class
Date
1.
What is the name of this carbonyl compound?
a)
pentan-2-one
b)
hexan-5-one
c)
pentan-3-one
d)
hexan-2-one
2.

What is the reagent for Fehling’s test?

a)

2,4-dinitrophenylhydrazine

b)

excess I2, NaOH

c)

Cu2+, OH-

d)

[Ag(NH3)2]+, OH-

3.

What is the positive observation for Tollens’ test?

a)

brick red precipitate

b)

silver mirror precipitate

c)

light yellow precipitate

d)

yellow or orange precipitate

4.

The product formed in Aldol condensation is

a)

an alpha, beta - unsaturated ester

b)

a beta hydroxy acid

c)

a beta hydroxy aldehyde or ketone

d)

an alpha hydroxy aldehyde or ketone

5.

Which one is the formula of ethanal?

a)
b)
c)
d)
6.

Compounds which do not undergo Crossed aldol condensation are -

a)

Formaldehyde and Acetaldehyde

b)

Acetaldehyde and Propionaldehyde

c)

Formaldehyde and Acetone

d)

Formaldehyde and Benzaldehyde

7.

identify reaction

a)

aldol

b)

cannizarro

c)

rosenmund

d)

etard

8.

To convert toulene to benzaldehyde reaction used is

a)

Gattermann koch

b)

Etard 's reaction

c)

Rosen mund

d)

aldol

9.

Acetophenone is prepared from

a)

Friedel craft reaction

b)

Rosenmund reaction

c)

Sandmayer reaction

d)

Wurtz reaction

10.

Choose the name reaction that produces benzaldehyde from Toluene and Chromyl chloride.

a)

Aldol condensation

b)

Gattermann Koch reaction

c)

Etard reaction

d)

Clemmensen reduction

11.

Which of the following is used in Rosenmund reduction?

a)

LiAlH4

b)

H2 /Pd-BaSO4

c)

Na/Ethanol

d)

NaBH4

12.

Choose the correct name of this molecule.

a)

propanol

b)

propanal

c)

propanone

d)

butanone

13.

Test for aldehyde

a)

Add Tollen’s reagent, warm to produce a silver mirror

b)

Add bromine water which changes from orange to colourless

c)

Add damp red litmus paper which turns blue

d)

Add silver nitrate which produces a white precipitate

14.

Type of mechanism that aldehydes and ketones undergo

a)

Electrophilic addition

b)

Nucleophilic addition

c)

Electrophilic substitution

d)

Nucleophilic substitution

15.

Aldehyde or ketone to alcohol

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

NaBH4 in aqueous ethanol at room temperature

16.

Aldehyde or ketone to hydroxynitrile

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

NaBH4 in aqueous ethanol at room temperature

17.

Aldehyde or ketone to alcohol

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

Hydrogen and nickel catalyst under high pressure

18.

Alcohol to alkene

a)

Acidified potassium dichromate, heat under reflux

b)

Conc. sulfuric acid, heat under reflux

c)

Potassium hydroxide in ethanol, heat

d)

Aqueous sodium hydroxide, heat under reflux

19.
What is the name of this carbonyl compound?
a)
pentan-2-one
b)
hexan-5-one
c)
pentan-3-one
d)
hexan-2-one
20.
Select carbonyl compounds from the following formulae:
a)
C4H10O
b)
C4H8O
c)
C4H8O2
d)
C4H8
21.
Classify the compound based on the functional group present.
a)
aldehyde
b)
ketone
c)
carboxylic acid
d)
ester
22.

Test for aldehyde

a)

Add Tollen’s reagent, warm to produce a silver mirror

b)

Add bromine water which changes from orange to colourless

c)

Add damp red litmus paper which turns blue

d)

Add silver nitrate which produces a white precipitate

23.

Test for aldehyde

a)

Add Fehling’s solution, heat gently to produce a red precipitate

b)

Add bromine water which changes from orange to colourless

c)

Add damp red litmus paper which turns blue

d)

Add silver nitrate which produces a white precipitate

24.

Aldehyde to carboxylic acid

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

NaBH4 in aqueous ethanol at room temperature

25.

Type of mechanism that aldehydes and ketones undergo

a)

Electrophilic addition

b)

Nucleophilic addition

c)

Electrophilic substitution

d)

Nucleophilic substitution

26.

Aldehyde or ketone to alcohol

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

NaBH4 in aqueous ethanol at room temperature

27.

Aldehyde or ketone to hydroxynitrile

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

NaBH4 in aqueous ethanol at room temperature

28.

Aldehyde or ketone to alcohol

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

Hydrogen and nickel catalyst under high pressure

29.

Primary alcohol to aldehyde

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

Hydrogen and nickel catalyst under high pressure

30.

Primary alcohol to carboxylic acid

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

Hydrogen and nickel catalyst under high pressure

31.

secondary alcohol to ketone

a)

Acidified potassium dichromate, heat and distil

b)

KCN followed by dilute sulfuric acid at room temperature

c)

Acidified potassium dichromate, heat under reflux

d)

Hydrogen and nickel catalyst under high pressure

32.

Alcohol to alkene

a)

Acidified potassium dichromate, heat under reflux

b)

Conc. sulfuric acid, heat under reflux

c)

Potassium hydroxide in ethanol, heat

d)

Aqueous sodium hydroxide, heat under reflux

33.

Colour change observed when acidified potassium dichromate reacts with an alcohol, aldehyde or ketone

a)

Green to orange

b)

Orange to colourless

c)

Orange to green

d)

Green to colour less

34.

Which of the following is mandatory for aldol condensation reaction

a)

presence of alpha hydrogen

b)

absence of alpha hydrogen

c)

presence of beta hydrogen

d)

absence of beta hydrogen

35.

Benzaldehyde on nitration gives

a)

o-nitrobenzaldehyde

b)

p-nitrobenzaldehyde

c)

m-nitrobenzaldehyde

d)

ortho and para dinitrobenzaldehyde

36.

The compound with the highest acidity in the following is

a)

4-methylbenzoic acid

b)

benzoic acid

c)

2-nitrobenzoic acid

d)

4-nitrobenzoic acid

37.

The reagent that does NOT oxidize aldehyde is

a)

CrO3

b)

acidic K2Cr2O7

c)

Ag2O

d)

alkaline KMnO4

38.

When reacted with a strong oxidising agent, aldehydes turn into

a)

carboxylic acids

b)

ketones

c)

primary alcohols

d)

secondary alcohols

39.

Which of the following alcohols can be oxidized to a ketone?

a)
b)
c)
d)
40.

Name this molecule:

a)

Propanone

b)

Propanal

c)

Butanone

d)

Butanal

41.
Aldehyde reacts with Tollen's reagent forming:
a)
Yellow precipitate
b)
Brick-red precipitate
c)
Purple solution
d)
Silver mirror
42.

2-butanol heated with acidified KMnO4 solution produced

a)

butanone

b)

butanoic acid

c)

butene

d)

butane

43.

Identify the functional group present in this compound.

a)

aldehyde

b)

ketone

c)

carboxylic acid

d)

ester

44.

Chemicals that contain a ketone functional group will end with....

a)

-al

b)

-ol

c)

-one

d)

-oic acid

45.

___________ commonly known as formaldehyde, was used as a biological preservative.

a)

Acetone

b)

Propanone

c)

Ethanol

d)

Methanal

46.

If ethanol is oxidised under reflux, the product will be

a)

Ethanoic Acid

b)

No Reaction

c)

Ethanone

d)

Ethanal

47.

Tollens' reagent shows the following colour change in a ketone

a)

Colourless to silver mirror

b)

Blue to brick red

c)

Stays colourless

d)

Stays blue

48.

Tollens' reagent shows the following colour change in an aldehyde

a)

Colourless to silver mirror

b)

Stays colourless

c)

Blue to brick red

d)

Stays blue

49.

Primary alcohols are oxidised to

a)

Ketones

b)

Carboxylic acids then aldehydes

c)

Aldehydes then carboxylic acids

d)

No reaction

50.

When reacted with a strong reducing agent, aldehydes turn into

a)

primary alcohols

b)

secondary alcohols

c)

ketones

d)

carboxylic acids

51.

Which of the following compounds reduces Ag+ ions to metallic Ag in ammoniacal silver nitrate solution?

a)

Aldehydes

b)

Ketones

c)

Carboxylic acids

d)

Alquenes

52.
a)

3-formylpentanal

b)

4-formylbutanodial

c)

3-ethylbutanodial

d)

4-formylbutanol

53.

Which aldehyde is a gas a room temperature?

a)

Benzaldehyde

b)

Cetaldehyde

c)

Formaldehyde

d)

None

54.

The functional group of aldehydes and ketones is

a)

carboxyl

b)

carbonyl

c)

hydroxyl

d)

carboalkoxy

55.

What is the IUPAC name of the compound given:

a)

2-pentanone

b)

5-pentanone

c)

hexanone

d)

2-hexanone

56.

Choose a FALSE statement about carbonyl compounds.

a)

Ketones can easily undegoes oxidation reaction

b)

Aldehydes are more reactive to undergoes nucleophilic addition compared to ketones

c)

Carbonyl is the functional group of aldehydes and ketones

d)

Structure of ketone consist of carbon carbonyl which attach to two alkyl/aryl groups

57.

Conversion of aldehyde to alcohol is

a)

Oxidation reaction

b)

Reduction reaction

c)

Esterification reaction

d)

Polymerisation reaction

58.

One of the nucleophilic addition of carbonyl compound is reaction with alcohol. The product form when ketone reacts by this reaction is

a)

acetal

b)

ketal

c)

hemiacetal

d)

hemiketal

59.

An aliphatic aldehydes gives positive result in Fehlings' test. It shows the formation of

a)

Silver mirror on the wall of test tube

b)

Light Yellow precipitate

c)

Brick-red precipitate

d)

Orange precipitate

60.

The product formed in Aldol condensation is

a)

an alpha, beta - unsaturated ester

b)

a beta hydroxy acid

c)

a beta hydroxy aldehyde or ketone

d)

an alpha hydroxy aldehyde or ketone

61.

Which of the following is used in Rosenmund reduction?

a)

LiAlH4

b)

H2 /Pd-BaSO4

c)

Na/Ethanol

d)

NaBH4

62.

Which reagent would you choose to convert 1-pentanol to pentanal?

a)

PCC in CH2Cl2

b)

K2Cr2O7 with aqueous H2SO4

c)

KMnO4 with aqueous H2SO4

d)

KOH, ethanol, reflux

63.

The only aldehyde that gives positive result with I2/NaOH is

a)

Butanal

b)

2-methylpropanal

c)

Ethanal

d)

Propanal

64.

Below are the reagents and conditions used for reduction except

a)

LiAlH4 ii. H3O+

b)

KMnO4, H+, heat

c)

NaBH4, Methanol

d)

H2, Pt

65.

What is the structural formula when cyclopentanone reacts with KCN, HCl

a)
b)
c)
d)
66.

Carbonyl compounds that give pale yellow precipitate with iodoform test must have contains..

a)

methyl carbinol group

b)

methyl carbonyl group

c)

carboxyl group

d)

carboalkoxy group

67.

The structure of 3-methyl-4-hydroxyhexanal is :

a)
b)
c)
d)
68.

Which structural formula is of 2,4-DNPH, a reagent to confirm the presence of carbonyl group.

a)

A

b)

B

c)

C

d)

D

69.

Adding alcohols to aldehydes gives

a)

Esters

b)

Carboxylic acids

c)

Ketones

d)

Hemiacetals & Acetals

70.

Adding alcohols to ketones gives

a)

Hemiacetals & Acetals

b)

Carboxylic acid

c)

Hemiketals & Ketals

d)

Water

71.
Select carbonyl compounds from the following formulae:
a)
C4H10O
b)
C4H8O
c)
C4H8O2
d)
C4H8
72.

What is the name for the compound shown?

a)

5-iodopentan-3-one

b)

5-iodopentan-2-one

c)

1-iodopentan-3-one

d)

1-iodopentan-2-one

73.

Give the IUPAC name for the following compound

a)

2-methyl-3-butanone

b)

3-methyl-3-butanone

c)

3-methyl-2-butanone

d)

3-methylbutanone

74.

What is the name of the mechanism when KCN (in acidic conditions) reacts with propanal?

a)

Free radical substitution

b)

Nucleophilic substitution

c)

Nucleophilic addition

d)

Electrophilic addition

75.

Name this molecule:

a)

Pentanoic acid

b)

2-hydroxy-2-methylbutan3-one

c)

3-hydroxy-3-methylbutane-2-one

d)

2-oxo-3-methylbutan-3-ol

76.

What will be formed if butanone is reacted with LiAlH4 in dry ether?

a)

Butanoic acid

b)

Butan-1-ol

c)

Butan-2-ol

d)

Butanal

77.

Acetophenone is prepared by

a)

Friedel craft reaction

b)

Rosenmund reaction

c)

Sandmayer reaction

d)

Wurtz reaction

78.

The Clemmenson reduction of acetone yields

a)

Ethanol

b)

Ethanal

c)

Propane

d)

Propanol

79.

Which of the following compounds does not contain an OH group

a)

Phenol

b)

Carboxylic acid

c)

Aldehydes

d)

Alcohols

80.

Catalyst SnCl2/ HCl is used in

a)

Stephen's reduction

b)

Cannizzaro reaction

c)

Clemmensen's reduction

d)

Rosenmund's reduction

81.

Ketones are prepared by

a)

Clemmensen's reduction

b)

Cannizzaro reaction

c)

Rosenmund's reduction

d)

Oppenaur's oxidation

82.

Which one of the following pairs is not correctly matched

a)

C=O_Clemmensons reduction_> >CH2

b)

>C=O Wolf Kishner Reduction> >CHOH

c)

-COCl Resunmund's reduction> - CHO

d)

-C = N Stefen's Reduction> -CHO

83.

Which of the following will not give the iodoform test

a)

Acetophenone

b)

Ethanal

c)

Benzophenone

d)

Ethanol

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