Paper 1 DP2 HL T2 2019

1. [1 mark]

Which is correct for the spectra of organic compounds?

A. Mass spectroscopy provides information about bond vibrations.

B. 1H NMR spectroscopy provides the values of carbon–hydrogen bond lengths.

C. Infrared spectroscopy provides the number of hydrogen atoms.

D. Mass spectroscopy provides information about the structure.

Markscheme

2. [1 mark]

What is the ratio of the areas of the signals in the 1H NMR spectrum of pentan-3-ol?

A. 6:4:1:1

B. 6:2:2:2

C. 5:5:1:1

D. 3:3:2:2:1:1

Markscheme

3. [1 mark]

What information is provided by 1H NMR, MS and IR for an organic compound?

I. 1H NMR: chemical environment(s) of protons

II. MS: fragmentation pattern
III. IR: types of functional group

A. I and II only

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 B. I and III only

C. II and III only

D. I, II and III

Markscheme

4. [1 mark]

What is the Index of Hydrogen Deficiency (IHD) for 1,3,5-hexatriene (C 6H8)?

A. 1

B. 3

C. 5

D. 6

Markscheme

5. [1 mark]

Ultraviolet radiation has a shorter wavelength than infrared radiation. How does the frequency and
energy of ultraviolet radiation compare with infrared radiation?

Markscheme

6. [1 mark]

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 What is name of this compound applying IUPAC rules?

A. E 1-bromo-1-chlorobut-1-ene

B. Z 1-bromo-1-chlorobut-1-ene

C. E 1-bromo-1-chloro-2-ethylethene

D. Z 1-bromo-1-chloro-2-ethylethene

Markscheme

7. [1 mark]

Propene is reacted first with hydrogen chloride to produce X which is then reacted with aqueous
sodium hydroxide to give Y. Finally, Y is reacted with excess acidified potassium dichromate solution.

What is the major product, Z?

A. CH3CH(OH)CH3

B. CH3COCH3

C. CH3CH2CHO

D. CH3(CH2)2COOH

Markscheme

8. [1 mark]

Which is the correct combination of substitution reaction mechanisms?

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 Markscheme

9. [1 mark]

Which combination best describes the substitution reaction between bromoethane and dilute aqueous
sodium hydroxide?

Markscheme

10. [1 mark]

What is the correct order for the increasing rate of hydrolysis of halogenoalkanes by dilute aqueous
sodium hydroxide?

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 A.

B.

C.

D.

Markscheme

11. [1 mark]

In organic reaction mechanisms, what does a curly arrow represent?

A. The movement of a pair of electrons towards a nucleophile

B. The movement of a pair of electrons towards a positively charged species

C. The movement of a pair of electrons away from a positively charged species

D. The movement of a pair of electrons towards a Lewis base

Markscheme

12. [1 mark]

Which factors affect the rate of nucleophilic substitution in halogenoalkanes?

I. The nature of the attacking nucleophile

II. The identity of the halogen

III. The structure of the halogenoalkane

A. I and II only

B. I and III only

C. II and III only

D. I, II and III

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 Markscheme

13. [1 mark]

1-bromobutane, , can be converted to 1-aminopentane,

, in a two-step process.

What are the reagents I and II?

Markscheme

14. [1 mark]

Which compound is optically active?

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 Markscheme

15. [1 mark]

Which reaction occurs via a free-radical mechanism?

A.

B.

C.

D.

Markscheme

16. [1 mark]

Which statement is correct about the enantiomers of a chiral compound?

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 A. Their physical properties are different.

B. All their chemical reactions are identical.

C. A racemic mixture will rotate the plane of polarized light.

D. They will rotate the plane of polarized light in opposite directions.

Markscheme

17. [1 mark]

Which would be the most effective method to distinguish between liquid propan-1-ol and propan-2-ol?

A. Observation of colour change when warmed with acidified potassium dichromate

B. Determination of m/z value of molecular ion in the mass spectrum

C. Determination of percentage composition

D. 1
H NMR spectroscopy

Markscheme

18. [1 mark]

Which compound gives this 1H NMR spectrum?

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 A. CH3CH2OCH2CH3

B. CH3CH2OH

C. CH3CH2CH3

D. CH3CH2CH2OH

Markscheme

19. [1 mark]

Which property explains why tetramethylsilane, Si(CH3)4, can be used as a reference standard in 1H
NMR spectroscopy?

A. It has a high boiling point.

B. It is a reactive compound.

C. All its protons are in the same chemical environment.

D. It gives multiple signals.

Markscheme

C
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20. [1 mark]

Which analytical technique is used to measure bond lengths in solid compounds?

A. IR spectroscopy

B. Mass spectroscopy

C. NMR spectroscopy

D. X-ray crystallography

Markscheme

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