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Alkenes

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Question 5

This question is about unsaturated hydrocarbons.

a.

Compound W (3,3-dimethylbut-1-ene) and compound X (hex-1-ene) are structural isomers. Compound W has a lower boiling point than compound X. Suggest why.

[2]
b.

Compound Y, CH3CH=CHCH2CH2OH\text{CH}_3\text{CH}=\text{CHCH}_2\text{CH}_2\text{OH}CH3​CH=CHCH2​CH2​OH, exists as cis and trans stereoisomers.

Identify the systematic IUPAC name for compound Y.

[1]
c.

Define the term stereoisomers.

[1]
d.

Explain how the structures of the cis and trans isomers of compound Y differ in spatial arrangement.

[2]
e.

Compound Z, CH2=C(CH3)CH2CH3\text{CH}_2=\text{C(CH}_3\text{)CH}_2\text{CH}_3CH2​=C(CH3​)CH2​CH3​, reacts with hydrogen bromide, HBr\text{HBr}HBr, by electrophilic addition. A mixture of two organic compounds, G and H, is formed.

Suggest how an HBr\text{HBr}HBr molecule can act as an electrophile.

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f.

Give the IUPAC names of the two addition products, G and H.

[2]
g.

State which of G and H is the major organic product, and explain your answer in terms of carbocation intermediate stability.

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h.

Myrcene, C10H16\text{C}_{10}\text{H}_{16}C10​H16​, is a naturally occurring acyclic unsaturated hydrocarbon containing three carbon-carbon double bonds.

Reaction of 408 mg408\text{ mg}408 mg of myrcene with hydrogen gas produces a saturated acyclic hydrocarbon. Calculate the volume of hydrogen gas, in cm3\text{cm}^3cm3 and measured at room temperature and pressure (RTP), needed to completely react with this mass of myrcene. (Take the molar volume of gas at RTP as 24000 cm3 mol−124000\text{ cm}^3\text{ mol}^{-1}24000 cm3 mol−1). Show your working.

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i.

Squalene is a naturally occurring, acyclic unsaturated hydrocarbon. A 0.00800 mol0.00800\text{ mol}0.00800 mol sample of squalene reacts completely with 1.152 dm31.152\text{ dm}^31.152 dm3 of hydrogen gas, measured at RTP, to form a saturated hydrocarbon. Using molecular formulas, construct a balanced equation for this reaction. Include relevant calculations and reasoning.

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Alkenes Questions

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