Ch 8, 9, 10 Pearson

Organic Chemistry summer

Provide the structure of the major organic product of the reaction below.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the peroxide serve in this reaction?

radical chain initiator

Name the major product which results when HBr is added to 3-ethyl-3-hexene.

3-bromo-3-ethylhexane

Provide the structure of the major organic product of the reaction below.

Provide the major organic product of the reaction below.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which of the following structures are formed during the mechanism?

Draw the major regioisomeric product generated in the reaction below.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Acid catalyzed hydration (H₂SO₄/water/△) of an unknown compound (A)with a chemical formula C₆H₁₂, yielded a racemic mixture of product C₆H₁₃OH. Which, if any, of the following compounds is/are possible structures for the initial compound (A)?

none of the above

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

What is the major product of the following reaction?

Which of the following intermediates is thought to occur in the mechanism by which alkenes are hydrated in the presence of acid?

carbocation

Complete the following reaction.

Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

oxymercuration-demercuration

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration sequence?

Markovnikov addition of H₂O wherein skeletal rearrangement is prevented

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

When an alkene is subjected to treatment with Hg(OAc)₂ in alcohol followed by reaction with NaBH₄, what new class of compound is formed?

ether

Treatment of 2-methylpropene with which of the following reaction conditions results in an anti-Markovnikov addition product?

both "dry gaseous HBr with peroxides present" and "BH3-THF, followed by alkaline H2O2"

Provide the structure of the major organic product of the reaction below.

Provide the structure of the major organic product of the reaction below.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Provide the reagents necessary to complete the following transformation.

1)BH3∗THF2)H2O2,HO−1)BH3∗THF2)H2O2,HO−

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Provide the major organic product of the reaction below.

Which of the following alkenes will yield a meso dihalide when reacted with Br₂/CCl₄ at room temperature?

Addition of Br₂ to (EE)-hex-3-ene produces ________.

a meso dibromide

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Both (EE)- and (ZZ)-hex-3-ene can be treated with D₂ in the presence of a platinum catalyst. How are the products from these two reactions related to each other?

The products of the two isomers are related as diastereomers.

________ is the use of an optically active reagent or catalyst to convert an optically inactive starting material into an optically active product.

Asymmetric induction

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Complete the following reaction by filling in the necessary reagents.

CH2I2/Zn(Cu)

Provide the reagents necessary to complete the following transformation.

mCPBA

Treatment of cyclopentene with peroxybenzoic acid ________.

yields a meso epoxide

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Provide the reagents necessary to complete the following transformation.

1)CH3CO3H2)H+,H2O

Provide the reagents necessary to complete the following transformation.

1) NaOH 2) H₂O, H⁺

Provide the reagents necessary to complete the following transformation.

OsO4,H2O2

Which of the following additions to alkenes occur(s) specifically in an syn fashion?

dihydroxylation using OsO₄, H₂O₂, addition of H₂, and hydroboration

Provide the major organic product of the following reaction.

Provide the reagents necessary to complete the following transformation.

OsO₄,H₂O₂

An unknown compound with empirical formula C₃H₅ was treated with Br₂/CCl₄. The bromine solution went from orangish/red to clear immediately at room temperature. Upon treatment with O₃ followed by work-up with dimethylsulfide the following products were identified. From the information provided what is/are the most likely structure(s) for this unknown compound.

How many moles of carbon dioxide are generated when one mole of the compound shown is treated with an excess of warm, concentrated KMnO₄ solution?

3

Provide the major organic product of the reaction below.

Draw the major organic products (two) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Which of the following compounds is (are) appropriate to promote the cationic polymerization of isobutylene?

both H₂SO₄ and BF₃

How many distinct alkynes exist with a molecular formula of C₄H₆?

2

How many distinct alkynes exist with a molecular formula of C₄H₈?

0

Give the new IUPAC name for HC≡≡CCH₂CH₂CH₃.

pent-1-yne

Draw an acceptable structure for acetylene.

Draw an acceptable structure for hex- 2-yne.

How many distinct terminal alkynes exist with a molecular formula of C₅H₈?

2

How many distinct internal alkynes exist with a molecular formula of C₆H₁₀?

3

Give the new IUPAC name for Cl₃CCH₂CH₂CH₂C≡CH.

6,6,6-trichlorohex-1-yne

Provide the IUPAC name for the compound below.

3-ethylhex-4-yn-3-ol

Provide the IUPAC name for Cl₃C(CH₂)₃C≡CH.

6,6,6-trichlorohex-1-yne

Name the compound shown below.

6,6-dimethylhept-3-yne

Give the IUPAC name for CH₃CH₂C≡CCH(OH)CH₃.

hex-3-yn-2-ol

Draw an acceptable structure for 3-sec-butylhept-1-yne.

Draw an acceptable structure for hepta-3,6-dien-1-yne.

What is the correct IUPAC name for the following compound?

3-(1-bromopropyl)-5-hexen-1-yne

Give the IUPAC name for CH₃CH=CHCH=CHC≡CCH₃.

octa-2,4-dien-6-yne

Which of the following improperly describes the physical properties of an alkyne?

insoluble in most organic solvents

Which of the following alkynes has the lowest boiling point?

3,3-dimethyl-1-butyne

How many moles of oxygen are required in the complete combustion of 1 mole of acetylene?

2.5

The pi bond of an alkyne is ________ and ________ than the pi bond of an alkene.

shorter, weaker

The carbon-carbon triple bond of an alkyne is composed of ________.

one σ bond and two π bonds

In trans-hept-4-en-2-yne the shortest carbon-carbon bond is between carbons ________.

2 and 3

Which of the species below is less basic than acetylide?

CH₃ONa

Among the compounds water, but-1-yne, but-2-yne, and ethane, which are stronger acids than ammonia?

water and but-1-yne

To a solution of propyne in diethyl ether, one molar equivalent of CH₃Li was added and the resulting mixture was stirred for 0.5 hour. After this time, an excess of D₂O was added. Describe the major organic product(s) of this reaction.

CH₃C≡CD + CH₄

Which of the following bases are sufficiently strong to deprotonate a terminal alkyne with an equilibrium constant greater than 1?

1) sodium methoxide 3) nn-butyl lithium
2) lithium diisopropyl amide 4) phenylmagnesium bromide

2, 3 and 4

What conditions could be used to isomerize hept-2-yne to hept-1-yne?

1.NaNH₂, 150 °C
2.H₂O

Why is a terminal alkyne favored when sodium amide (NaNH₂) is used in an elimination reaction with 2,3-dichlorohexane?

The strong base deprotonates the terminal alkyne and removes it from the equilibrium

When 2,2-dibromobutane is heated at 200°C in the presence of molten KOH, what is the major organic product?

but-2-yne

Describe a sequence of reactions by which hept-1-yne can be straightforwardly prepared from hept-1-ene.

1) Br₂; 2) NaNH₂, heat.

Complete the short synthesis below by providing the necessary reagents.

1)Br2;2)CH3C≡CNa;3)Na/NH3

Which of the following describes an unsymmetrical addition reaction?

propyne with 1 mole HBr

Which of the following reagents will convert 1 mole of 3-methylpent-1-yne into 3-methylpentane?

2 moles H₂, Ni and heat

Describe a sequence of reactions by which trans-pent-2-ene can be straightforwardly prepared from propyne.

1) NaNH₂; 2) CH₃CH₂Br; 3) Na, NH₃.

Which of the following reagents should be used to convert hex-3-yne to (EE)-hex-3-ene?

Na, NH₃

Which of the following reagents should be used to convert hex-3-yne to (ZZ)-hex-3-ene?

H₂, Lindlar's catalyst

A mixture of hept-1-yne, hept-2-yne, and hept-3-yne was hydrogenated in the presence of a platinum catalyst until hydrogen uptake ceased. If one assumes that the hydrogenation went to completion, how many different seven-carbon hydrocarbons were produced?

1

________ is produced when 1 equivalent of HBr is added to hex-1-yne in the presence of peroxides.

A mixture of E and Z isomers of 1-bromohex-1-ene

Which of the alkyne addition reactions below involve(s) an enol intermediate?

both hydroboration/oxidation and treatment with HgSO₄ in dilute H₂SO₄

What is the major organic product that results when 1-heptyne is treated with 2 equivalents of HBr?

2,2-dibromoheptane

What class of organic product results when 1-heptyne is treated with a mixture of mercuric acetate in aqueous sulfuric acid?

ketone

What class of organic product results when 1-heptyne is reacted with disiamylborane followed by treatment with basic hydrogen peroxide?

aldehyde

Name the compound which results when pent-1-yne is treated with sodium in liquid ammonia.

pent-1-ene

Provide the major organic product of the reaction shown below.

Provide the major organic product of the reaction shown below.

Provide the structure of the major organic product(s) in the reaction below.

Provide the structure of the major organic product(s) in the reaction below.

Provide the major organic product of the reaction shown below.