Question 1

Which of the following correctly names the compound with the structure $$CH_3CH_2C\equiv CH$$?

Accepted Answer

1-butyne

Question 2

Why is the hydrogen atom on a terminal alkyne (such as $$HC\equiv $$CCH_3$$) unusually acidic compared to other hydrocarbons?

Accepted Answer

The sp-hybridized carbon holds the negative charge more stably due to higher s-character.

Question 3

What is the major product when 2-butyne reacts with $$H_2 in $$the presence of Lindlar's catalyst?

Accepted Answer

cis-2-butene

Question 4

A student treats 2-butyne with sodium metal in liquid ammonia ($$Na^0$$/$$NH_3). $$What is the expected major product?

Accepted Answer

trans-2-butene

Question 5

When excess $$HBr is $$added to 1-butyne, what is the major organic product?

Accepted Answer

2,2-dibromobutane

Question 6

Which reagent sequence will convert 1-hexyne to hexan-2-one?

Accepted Answer

$$H_2SO_4$$, $$HgSO_4$$, $$H_2O$$

Question 7

Hydroboration-oxidation of 1-hexyne produces which major product?

Accepted Answer

hexan-1-one

Question 8

What is the expected product when 2-butyne is treated with excess $$Br_2$$?

Accepted Answer

1,1,2,2-tetrabromobutane

Question 9

A terminal alkyne is deprotonated with $$NaNH_2$$ and then reacted with 1-bromopropane. What is the major product?

Accepted Answer

An internal alkyne with a new three-carbon chain attached to the terminal carbon

Question 10

Which of the following statements about haloalkanes is TRUE?

Accepted Answer

Haloalkanes tend to be denser than water.

Question 11

Which factor most strongly increases the boiling point of a haloalkane?

Accepted Answer

The size and polarizability of the halogen atom

Question 12

What is the correct IUPAC name for the following compound: $$CH_2BrCH_2CH_2C\equiv CH$$?

Accepted Answer

4-bromo-1-pentyne

Question 13

Which of the following best describes the mechanism of hydration of an alkyne using $$H_2SO_4$$, $$HgSO_4$$, and $$H_2O$$?

Accepted Answer

Enol formation followed by tautomerization to a ketone

Question 14

A chemist wants to synthesize trans-2-butene from 2-butyne. Which reagent should they use?

Accepted Answer

$$Na^0 in$$ $$NH_3$$

Question 15

Which product is formed when 1-hexyne is treated with $$B(sia)_2H$$ followed by $$H_2O_2$$ and $$NaOH$$?

Accepted Answer

hexan-1-one

Question 16

Which of the following is a correct statement about the addition of $$Br_2 to an $$alkyne?

Accepted Answer

The bromines add trans to each other in the alkene product.

Question 17

Which of the following haloalkanes would have the highest boiling point?

Accepted Answer

1-iodopentane

Question 18

A multi-step synthesis starts with 1-butyne. Step 1: $$NaNH_2$$; Step 2: 1-bromopropane; Step 3: $$H_2SO_4$$, $$HgSO_4$$, $$H_2O. $$What is the final major product?

Accepted Answer

2-hexanone

Question 19

Which of the following statements about the solubility of haloalkanes in water is correct?

Accepted Answer

Larger haloalkanes are less soluble in water.

Question 20

Which of the following reactions would convert a terminal alkyne into an internal alkyne?

Accepted Answer

Deprotonation with $$NaNH_2$$ followed by reaction with a haloalkane

Alkynes and Haloalkanes: Properties, Reactions, and Nomenclature

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