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Chapt2-10

Total questions: 63

Worksheet time: 32mins

Name
Class
Date
1.

Give a correct statement

a)

The acidity of H-A increases with the presence of electron-withdrawing groups in A

b)

The acidity of H-A increases with the presence of electron-donating groups in A

c)

The acidity of H-A does not affect by presence of a constituent group in A

d)

The more acidity, the less stable conjugate base

2.

6. What is the best description on hydrophobic and/or hydrophilic moieties

a)

Hydrophobic moiety is a nonpolar part of a molecules that is not

attracted to water. Hydrophilic moiety is a polar part of a molecules

that is attracted to water.

b)

Hydrophobic moiety is a polar part of a molecules that is attracted to

water. Hydrophilic moiety is a nonpolar part of a molecules that is not

attracted to water.

c)

Hydrophobic moiety easily dissolve in polar solvents.

d)

Hydrophilic moiety easily dissolve in nonpolar or weakly polar

solvents.

3.

Rank the compounds in order to increase melting point

a)

CH3(CH2)6CH3, (CH3)3CC(CH3)3, CH3CH(CH3)CH2CH2CH2CH2CH3

b)

(CH3)3CC(CH3)3, CH3CH(CH3)CH2CH2CH2CH2CH3, CH3(CH2)6CH3

c)

CH3CH(CH3)CH2CH2CH2CH2CH3, (CH3)3CC(CH3)3, CH3(CH2)6CH3

d)

CH3CH(CH3)CH2CH2CH2CH2CH3, CH3(CH2)6CH3, (CH3)3CC(CH3)3

4.

Which statement is incorrect on reaction of alkyl halides

a)

Alkyl halides undergo nucleophilic substitution reactions with nucleophiles

b)

Alkyl halides undergo dehydrohalogenation reactions with Bronsted-Lowry

bases

c)

Alkyl halides undergo electrophilic substitution reactions with benzene

derivatives

d)

Alkyl halides undergo elimination reactions with Lewis acids

5.

Which is correct description on physical properties of alkenes

a)

Alkenes are soluble in water and insoluble in organic solvents

b)

Cis-isomer is more polar than Trans-isomer

c)

Trans-isomer has lower melting point than Cis-isomer

d)

Alkenes have higher melting point and boiling point than corresponding alkanes

6.

Give numbers of constitutional isomers of alkyne having molecular formula C6H10

a)

5

b)

6

c)

7

d)

8

7.

Give major product of reaction between terminal alkynes with 1 equivalent of hydrogen halide

a)

E or Z vinyl halide compound

b)

A saturated compound that both halogen atoms bond to the terminal carbon

c)

An alkenyl halide that H atom bond to the terminal carbon

d)

A saturated compound that both H atoms bond to the terminal carbon

8.

Give major product(s) of bellow reactions

a)

CH3-C≡CNa + H2

b)

Propynylcyclohexane

c)

Cyclohexene

d)

Propylcyclohexane

9.

Give a compound that has anaesthetic property

a)

Diethyl ether

b)

Dimethyl ether

c)

Ethanol

d)

Methanol

10.

Which compound is synthesized through an intramolecular SN2 reaction

a)

A alcohol

b)

An epoxide

c)

An ether

d)

All of these statements

11.

Which statement is incorrect about epoxides.

a)

Epoxides are capable of intermolecular hydrogen bonding

b)

Epoxides are soluble in organic solvents

c)

Epoxides are named in three different ways, including epoxyalkanes, oxiranes, and alkene oxides

d)

Epoxides are ether having the oxygen atom in a three-membered ring

12.

Rank capable of intermolecular hydrogen bonding and steric hindrance among primary, secondary and tertiary alcohols

a)

Increasing both ability to hydrogen bonding and steric hindrance

b)

Decreasing ability to hydrogen bonding and increasing steric hindrance

c)

Increasing ability to hydrogen bonding and decreasing steric hindrance

d)

Decreasing both ability to hydrogen bonding and steric hindrance

13.

Which statement is correct about general reactions of alcohols, ethers, and epoxides.

a)

Nucleophilic groups react with epoxides but do not react with neither alcohols nor ethers

b)

Ethers undergo dehydration to give alkenes

c)

Alcohols generally react with halide anions to give alkyl halides

d)

Ethers react with strong acid to give corresponding alcohols

14.

Give a correct statement on dehydration of alcohols to form alkenes

a)

Reactivity decreases as decreasing of alcohol order

b)

Major product is followed Zaitsev rule

c)

Reaction occur through E1 or E2 mechanism

d)

All of these statements

15.

Give mechanism of ether cleavage reaction

a)

Only SN1

b)

Only SN2

c)

Both SN1 and SN2

16.

The 2,2-dimethylcyclopentanol underwent dehydration in sulfuric acid to form alkenes. Give the best description for the product(s)

a)

1

b)

2 3 4

c)

1 2 3 4

d)

None

17.

Give the most acidic hydrogen atom among bellow molecules

a)

1

b)

2

c)

3

d)

4

18.

Which statement is incorrect on structure of aldehydes, ketones, and carbonyl group

a)

The carbonyl group consists of one σ-bond and one π-bond

b)

The functional group of an aldehyde is a carbonyl group bound to at least one H-atom

c)

The functional group of a ketone is a carbonyl group bound to two carbon atoms

d)

The carbonyl group is strong electron donating group

19.

Which statement is correct on the tautomerism and tautomers

a)

Tautomerism commonly results from the relocation of a hydrogen atom with thin the compound

b)

Contitutional isomers are tautomers

c)

Tautomers readily interconvert each other

d)

The two tautomers of an amino acid are neural and zwitterionic forms

20.

Give a method to synthesize aldehydes

a)

Oxidation of secondary alcohols with PCC (Pyridinium chlorochromate)

b)

Hydroboration-oxidation of terminal alkyne

c)

Hydration of alkyne, except acetylene

d)

By Friedel-Crafts acylation

21.

Which statement is incorrect on physic properties of aldehydes and ketones

a)

Aldehydes and ketones exhibit dipole–dipole interactions

b)

Aldehydes and ketones are soluble in organic solvents

c)

Aldehydes and ketones have lower boiling point and melting point compare to corresponding alcohols

d)

Aldehydes and ketones are capable of intermolecular hydrogen bonding

22.

Which is incorrect general feature-reactions of aldehydes and ketones

a)

Nucleophilic addition to the carbonyl group

b)

Reaction of carbonyl group with a Bronsted or Lewis base

c)

Reaction of carbonyl group with a Bronsted or Lewis acid

d)

Reaction at alpha-carbon of carbonyl group

23.

Which of the following reactions give a proposed product

a)

b)

c)

d)

24.

What alkene yields acetone and formaldehyde after treatment with ozone followed by CH3SCH3

a)

Ethene

b)

2,3-dimethylbut-2-ene

c)

) 2-methylpropene

d)

Cis or Trans-but-2-ene

25.

Give numbers of constitutional isomers of C8H12 which undergoes the oxidative cleavage of alkenes to give only 3-oxobutanal (CH3COCH2CHO).

a)

1

b)

2

c)

3

d)

4

26.

Propanoic acid could be formed when 1-propanol

reacts with:

a)

Sulfuric acid (catalytic amount), heat at 200°C

b)

Sulfuric acid (catalytic amount), heat at 140°C

c)

Pyridinium chlorochromate (PCC) in

dichloromethane

d)

Potassium dichromate (K2Cr2O7) in aqueous

sulfuric acid, heat

27.

What group in order of increasing boiling point?

a)

CH3CH2CH2)2O, CH3(CH2)5OH CH3CH2CH2CH2COOH

b)

CH3COCH2CH(CH3)2, (CH3)2CHCH2COOH, (CH3)2CHCH2CH(OH)CH3

c)

CH3CH2CH2CH2OH, CH3CH2CH(OH)CH3, CH3CH2CH2CH2Cl, CH3CH2CH2CH2COOH

d)

HCCH, CH2=CH2, CH3CH3.

28.

What group in order of decreasing reactivity in nucleophilic acyl substitution?

a)

CH3CH2CH2COOCH2CH2CH3,CH3CH2CONH2, CH3CH2COCl

b)

CF3CO)2O, (CH3CH2CO)2O, CH3CH2COOCH2CH2CH3

c)

CH3COOH, CH3COCl, CH3COSH

d)

HCOOH, CH3CH2COOH, CH3COOH

29.

Choose group of the compounds in order of decreasing acidity

a)

Acetic acid, ethanol, ethane

b)

Benzene, benzoic acid, benzyl alcohol

c)

Propanedioic acid, propanoic acid, 1,3-propanediol

d)

trifluoromethanesulfonic acid (CF3SO2OH), acetic acidC, trifluoroacetic acid, 2,2,2-trifluoroethanol, ethanol.

30.

There are various methods that can be used for the preparation of Carboxylic acids.

a)

By using primary Alcohols and Aldehyde

b)

From Nitriles and Amides.

c)

By using Grignard Reagents

d)

All mentioned methods are corrected

31.

Which of the following should be the most volatile?

a)

CH3CH2CH2NH2

b)

(CH3)3N

c)

CH3CH2NHCH3

d)

CH3CH2CH2CH3

32.

When excess of ethyl iodie is treated with ammonia, the product is:

a)

ethylamine

b)

diethylamine

c)

triethylamine

d)

Tetraethylamimoniu iodide

33.

Benzoic acid is treated with SOCl2 and the product X formed is reacted with ammonia to give Y. Y in the reaction is

a)

Aniline (C6H5NH2)

b)

benzamide (C6H5CONH2)

c)

chlorobenzene (C6H5Cl)

d)

Benzoyl chloride (C6H5COCl)

34.

Give reaction sequent:e

a)

CH3CH2CH2NHCOCH3

b)

CH3CH2CH2NH2

c)

CH3CH2CH2CONHCH3

d)

CH3CH2CH2CONHCOCH3

35.

Which of the following statements is false?

a)

The base-promoted ring-opening of an epoxide using aqueous NaOH will yield a trans glycol

b)

The catalyzed ring-opening of an epoxide in aqueous acid will yield a cis glycol

c)

Treatment of an unhindered epoxide with a Grignard reagent will result in a

nucleophiliccah oih attack at the less hindered carbon

d)

A nucleophile attacks an epoxide to yield an alcohol

36.

. 1-phenylethanol can be prepared by the reaction of methyl iodide and magnesium with

a)

Bromobenzene

b)

Acetophenone

c)

Benzaldehyde

d)

Benzyl alcohol

37.

. Which of the isomeric C4H10O alcohol(s) can be prepared by hydrogenation of aldehyde?

a)

Butan-1-ol

b)

Butan-1-ol and butan-2-ol

c)

. 2-methylpropan-2-ol and 2-methylpropan-1-ol

d)

Butan-1-ol and 2-methylpropan-1-ol

38.

The reaction of a Grignard reagent with ethylene oxide (oxirane) followed by work-up with dilute acid gives which of the following products?

a)

. A secondary alcohol

b)

No alcohol

c)

A primary alcohol

d)

Ethanol

39.

Cyclopentanol could be prepared from NaOH with the reagent:

a)

chlorocyclopentane

b)

cycloentane

c)

methylcyclopentyl ether

d)

cyclopentanamine

40.

What is the product of a hydroboration–oxidation reaction with 1-hexylcyclohexene?

a)

2-hexylcyclohexanol

b)

Hexylcyclohexane

c)

3-hexylcyclohexanol

d)

. 1-hexylcyclohexanol

41.

Which compound is a Lewis acid?

a)

AlCl3

b)

CH3+

c)

(CH3)3N

d)

FeCl3

42.

Which compound is a Lewis acid?

a)

BH3

b)

NH3

c)

CH3O-

d)

FeCl3

43.

Which of these would react fastest with methanol via an SN1 mechanism?

a)

(CH3)2C(Br)CH2CH3

b)

CH3CH2CH2CHBrCH3

c)

CH3CH2CH2CH2CH2Br

d)

(CH3)3CCH2Br

44.

Hexanal, the major organic product isolated from the reaction of 1-hexyne with

a)

borane (BH3) in tetrahydrofuran (THF) then hydroperoxide (H2O2) in sodium hydroxide (NaOH)

b)

borane (BH3) in tetrahydrofuran then hydrolysis in sodium hydroxide

c)

Aqueous sulfuric acid, mercury(II) sulfate

d)

Ozone followed by hydrolysis

45.

Give the reaction sequence.

a)

HCOOH

b)

OCH-CHO

c)

CH3CH2CHO

d)

CH3CH2COOH

46.

Dipropyl ether could be formed when 1-propanol reacts with:

a)

Sulfuric acid (catalytic amount), heat at 200°C

b)

Sulfuric acid (catalytic amount), heat at 140°C

c)

Pyridinium chlorochromate (PCC) in dichloromethane

d)

Potassium dichromate (K2Cr2O7) in aqueous sulfuric acid, heat

47.

Give the reaction:

C6H5CH2CHO ->C6H5CH2CH=NCH(CH3)2

What reagent(s) will successfully complete the synthesis reaction shown above?

a)

(CH3)2CHNH2, strong acid

b)

. (CH3)2CHNH2, strong base

c)

CH3)2CHNH2, mild acid

d)

(CH3)3CNH2, mild acid

48.

Main products of above reactions are

a)

1 3

b)

2 3

c)

1 4

d)

2 4

49.

Which of the following best describes what happens in the first step in the mechanism of the hydrogen–deuterium exchange reaction shown?

a)

1

b)

2

c)

3

d)

4

50.

Nucleophilic addition can occur with alkynes that bear strong electron-attracting

substituents such as CF3 on the triple bond. Predict the product of nucleophilic addition of CH3OD to 3,3,3-trifluoropropyne. The stereochemistry of addition is anti, and the first step in the mechanism is bond formation between CH3O− and one of the carbons of the triple bond.

a)

1

b)

2

c)

3

d)

4

51.
a)

1

b)

2

c)

3

d)

4

52.

Like the pinacol rearrangement in the preceding problem, this one also begins with the formation of the more stable of two possible carbocations from a vicinal diol. A 99% yield of a single ketone was isolated. What is this ketone?

a)

1

b)

2

c)

3

d)

4

53.

Determine the double bond stereochemistry (E or Z) for the following molecules.

a)

A: E; B: E

b)

A: Z; B: Z

c)

A: E; B: Z

d)

A: Z; B: E

54.

Which of the following compounds would be the best nucleophile?

a)

H2O

b)

CH3S−

c)

CH3O−

d)

NH3

55.

Biological oxidation of the hydrocarbon adamantane by the fungus Absidia glauca gives a mixture of two alcohols. Classify the carbon in adamantane that is oxidized in forming the major product.

a)

Primary

b)

Secondary

c)

Tertiary

d)

Quaternary

56.

Indicate the relationships between the two molecules as enantiomers, diastereomers, or same molecules

a)

I: same molecule, II: same molecule, III: diastereomers

b)

I: enatiomers, II: same molecule, III: diastereomers

c)

I: enatiomer, II: enatiomers, III: diastereomers

d)

I: enatiomer, II: same molecule, III: same molecule

57.
a)

1

b)

2

c)

3

d)

4

58.
a)

1

b)

2

c)

3

d)

4

59.

Which compound undergoes substitution by the SN2 mechanism at the fastest rate?

a)

1

b)

2

c)

3

d)

4

60.

Which compound undergoes substitution by the SN1 mechanism at the fastest rate?

a)

1

b)

2

c)

3

d)

4

61.

Aldehyde could be prepared by

a)

Reduction of carboxyl compounds and oxydation of primary alcohols

b)

Reduction of carboxyl compounds and oxydation of secondary alcohols

c)

Oxydation of carboxyl compounds and oxydation of primary alcohols

d)

oxidation of carboxyl compounds and reduction of primary alcohols

62.

Muscarine is a poisonous substance present in the mushroom Amanita muscaria. Its struture is represented by the constitution show here

a)

6

b)

7

c)

8

d)

9

63.
a)

1

b)

2

c)

3

d)

4

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