Question 1

What is the correct IUPAC name for the compound shown in question 1a (a straight chain with a triple bond at the second carbon and a double bond at the fourth carbon)?

Accepted Answer

$$4-$$Hexen$$2-$$yne

Question 2

Which of the following best describes the product of the reaction: $$\mathrm{Ph{-}CH_2${-}CH=CH_2$}$$ treated with $$\mathrm{Hg(OAc)_2, H_2O}$$ followed by $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

$$\mathrm{Ph{-}CH_2${-}CHOH{-}CH_3$}$$

Question 3

What is the major product when $$\mathrm{Ph{-}CH_2${-}CH=CH_2$} is $$treated with $$\mathrm{Br_2$/H_2O}$$?

Accepted Answer

$$\mathrm{Ph{-}CH_2${-}CH(OH)CH_2Br}$$

Question 4

Which of the following is the correct product for the reaction of $$\mathrm{Ph{-}CH=CH_2$}$$ with HBr?

Accepted Answer

$$\mathrm{Ph{-}CH_2${-}CH_2Br}$$

Question 5

What is the product when $$\mathrm{Ph{-}C \equiv C{-}CH_3$} is $$treated with $$2\ \mathrm{Br_2$/ $$CCl_4$$}$$?

Accepted Answer

$$\mathrm{Ph{-}$$CBr_2$${-}$$CBr_2$${-}CH_3$}$$

Question 6

Which product is formed when $$\mathrm{Ph{-}C \equiv C{-}CH_3$} is $$hydrogenated with Lindlar's catalyst?

Accepted Answer

$$\mathrm{Ph{-}CH=CH{-}CH_3$} ($$cis)

Question 7

What is the product of hydroboration-oxidation ($$1.\ \mathrm{BH_3$},\ 2.\ \mathrm{NaOH/H_2O_2}) of$$ $$\mathrm{Ph{-}C \equiv C{-}CH_3$}$$?

Accepted Answer

$$\mathrm{Ph{-}CH_2${-}$$COCH_3$$}$$

Question 8

Which reagent sequence would convert phenylacetylene ($$\mathrm{Ph{-}C \equiv CH}) to$$ $$\mathrm{Ph{-}C \equiv C{-}CH_2CH_3}$$?

Accepted Answer

1. $$\mathrm{$$NaNH_2$$}$$, 2. $$\mathrm{CH_3CH_2Br}$$

Question 9

Which of the following best describes the regioselectivity of hydroboration-oxidation of terminal alkynes?

Accepted Answer

Anti-Markovnikov addition of water, forming an aldehyde

Question 10

Which of the following is the correct product for the hydration of phenylacetylene ($$\mathrm{Ph{-}C \equiv CH}) $$with $$\mathrm{$$HgSO_4$$, H_2SO_4, H_2O}$$?

Accepted Answer

$$\mathrm{Ph{-}$$COCH_3$$}$$

Question 11

Which of the following statements about Lindlar's catalyst is correct?

Accepted Answer

It selectively hydrogenates alkynes to cis-alkenes

Question 12

Which of the following is a common use of sodium amide ($$\mathrm{$$NaNH_2$$}) in $$organic synthesis?

Accepted Answer

Deprotonation of terminal alkynes to form acetylide ions

Question 13

Which of the following best describes the product of the reaction: $$\mathrm{CH_3${-}C \equiv CH}$$ treated with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

$$\mathrm{CH_3${-}$$CBr_2$${-}$$CHBr_2$$}$$

Question 14

Which of the following is the correct IUPAC name for the compound in question 1d (a six-membered ring with a methyl group and a double bond)?

Accepted Answer

1-Methylcyclohexene

Question 15

Which of the following is the correct product for the reaction: $$\mathrm{Ph{-}C \equiv CH}$$ treated with $$\mathrm{H_2$}$$ and Lindlar's catalyst?

Accepted Answer

$$\mathrm{Ph{-}CH=CH_2$} ($$cis)

Organic Chemistry 141: Nomenclature and Reaction Mechanisms (Chapters 8 & 9)

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