Chapter 15 Question Preview - S210

Start Date:   27 Jul 2010 at 10:00 AM
Due Date:   Unlimited
Student Access after Due Date:    Yes. Attempts after Due Date will be Marked Late
Graded:    Yes
15.02.05 Alkanes

Draw all possible structures for C6H14.

15.02.06 Alkanes

Draw all possible structure(s) and give the IUPAC systematic name(s) of an alkane or cycloalkane with the formula C6H12, that has only secondary hydrogen atoms.

Draw the structure(s).

Select the IUPAC systematic name(s) (all drawn in previous step):

cyclohexane

1,2-dimethylcyclobutane

methylcyclopentane

3-methylpentane

hexene

1,1-dimethylcyclobutane

2-methylpentane

ethylcyclobutane
15.02.07 Alkanes

Draw all possible structure(s) and give the IUPAC systematic name(s) of an alkane or cycloalkane with the formula C6H12, that necessarily has only primary and secondary hydrogen atoms.

Draw the structure(s).

Select the IUPAC systematic name(s) (all drawn in previous step):

cyclohexane

hexane

2-methylheptene

1,1-dimethylcyclobutane

1,2-dimethylcyclobutane

hexene

2-methylpentene

methylcyclopentane
15.02.08 Alkanes

Draw all possible structure(s) and give the IUPAC systematic name(s) of all cycloalkanes with the formula C8H14, that has 12 secondary and 2 tertiary hydrogen atoms.

Draw the structure(s).

Select the IUPAC systematic name(s) (all drawn in previous step):

Bicyclo[5.1.0]octane

Bicyclo[4.2.0]octane

Bicyclo[2.2.2]hexane

Bicyclo[4.1.1]octane

Bicyclo[3.3.0]octane

Bicyclo[4.1.1]hexane

Bicyclo[3.2.1]octane

Bicyclo[2.2.2]octane
15.02.09 Alkanes

Draw all possible structures for C7H16.

15.02.10 Alkanes

Give the IUPAC name for this compound.

15.02.11 Alkanes

Draw structural formula for decane.

15.02.12 Alkanes

Give the systematic IUPAC name for the following.
Note: An example of the correct answer format is 2,3-dimethylpentane. Do not include spaces between commas and/or hyphens.



15.02.13 Alkanes

Draw structural formula of this compound: 2,4-dimethylpentane.

15.02.14 Alkanes

Using bond line formulas select the two chair conformations of cis-1-tert-butyl-3-methylcyclohexane.

Select the more stable chair conformations of cis-1-tert-butyl-3-methylcyclohexane.

15.02.15 Alkanes

Give systematic IUPAC names for .



15.02.16 Alkanes

Draw structural formula of this compound: 2,2-dimethylpentane.

15.02.17 Alkanes

Draw structural formula of this compound: 3-isopropyloctane.

15.02.19 Alkanes

Consider the following pairs of structures. Choose the configuration of chirality center (R or S) of each of the following compound. If there is more than 1 chirality center, enter the configuration of the center marked with *. Choose "None" if it is not possible to determine configuration. Identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use hand-held molecular models to check you answers.

The configuration for the left compound is , for the right is

Presented compounds are:

constitutional isomers

diastereomers

enantiomers

two molecules of the same compound

The configuration for the left compound is , for the right is

Presented compounds are:

diastereomers

two molecules of the same compound

constitutional isomers

enantiomers

The configuration for the left compound is , for the right is

Presented compounds are:

enantiomers

two molecules of the same compound

diastereomers

constitutional isomers
15.02.20 Alkanes

Select structures for compounds E-H.

Compound E has the molecular formula C5H8 and is optically active. On catalytic hydrogenation E yields F. Compound F has the molecular formula C5H10, is optically inactive, and cannot be resolved into separate enantiomers.
E is:

F is:

Compound G has the molecular formula C6H10 and is optically active. Compound G has no triple bonds. On catalytic hydrogenation G yields H. Compound H has the molecular formula C6H14, is optically inactive, and cannot be resolved into separate enantiomers.
G is:

H is:

15.02.21 Alkanes

Choose the line structure formula for 3-methylcyclobutene.



15.03.01 Alkenes and Alkynes

The following are incorrect names. Match the incorrect name with the correct one. Match each of the numbered items in the list with the numbers in the drop-down menus:
2-isopropylbut-2-ene
hex-4-yne
3,3-dimethylpentene
2-methylcyclohexene
pent-3-ene
1-methylpropene

1.3,3-dimethylpent-1-ene
2.but-2-ene
3.hex-3-yne
4.pent-2-ene
5.3,4-dimethylpent-2-ene
6.1-methylcyclohexene

15.03.15 Alkenes and Alkynes

Below is the structure of vitamin A.



How many isoprene units are there?

Which of the following represents the head-to-tail and cross-linked isoprene units? The linkages are represented by dashed lines.

15.03.16 Alkenes and Alkynes

Select the more stable carbocation.

15.03.17 Alkenes and Alkynes

Give the IUPAC name for this compound.

15.03.18 Alkenes and Alkynes

Give the IUPAC name for this compound.

15.03.19 Alkenes and Alkynes

Give the IUPAC name for this compound.

15.03.20 Alkenes and Alkynes

Give the IUPAC name for this compound.

15.03.21 Alkenes and Alkynes

Draw all possible structures for C5H10 (ignore cis/trans isomerism).

15.03.22 Alkenes and Alkynes

Draw structures containing two carbon atoms for the following class of compounds: alkene.

15.03.23 Alkenes and Alkynes

Select correct structures for the following:

3,3,3-Tribromopropene is:

(Z,4R)-4-Methyl-2-hexene is:

15.03.24 Alkenes and Alkynes

Give the IUPAC names for each of the following molecules. Designate stereochemistry and double-bond isometry if present.
is
is

15.03.25 Alkenes and Alkynes

Choose the bond line formula for (Z, 4R)-4-methyl-2-hexene.   

15.03.27 Alkenes and Alkynes

Draw structures containing two carbon atoms for the following class of compounds: alkyne.

15.03.28 Alkenes and Alkynes

Draw structural formula for 1,1-dibromoethene.

15.03.29 Alkenes and Alkynes

Draw structural formula for trans-2,5-dimethylhex-3-ene.

15.03.30 Alkenes and Alkynes

Draw structural formula for 2-ethyl-3-methylpent-1-ene.

15.03.31 Alkenes and Alkynes

Draw structural formula for 4-methylpent-2-ene.

15.05.01 Reactions of Alkenes

How do you convert ethylene into the following? Match the reagents with the product:

chloroethane
1,2-ethanediol
1,2-dibromoethane
bromoethane
ethanol
ethane

1.Br2
2.H2/Pt
3.OsO4/ROOH
4.H2O/H2SO4
5.HCl
6.HBr
15.05.37 Reactions of Alkenes

Cuparene and herbertene are naturally occuring compounds isolated from various species of lichen:



Determine whether one or both of these compounds can be classified as terpenes.

Herbertene

Cupartene

15.05.38 Reactions of Alkenes

Which alkene will react with Br2 to give the following product? There may be more than one answer.



15.05.39 Reactions of Alkenes

Which alkene will react with Br2 to give the following product? There may be more than one answer.



15.05.40 Reactions of Alkenes

Which alkene will react with Br2 to give the following product? There may be more than one answer.



15.05.41 Reactions of Alkenes

The addition of bromine or chlorine to cycloalkenes is stereoselective. Predict the product for the following reaction.

1-methylcyclohexene + Br2

15.05.42 Reactions of Alkenes

The addition of bromine or chlorine to cycloalkenes is stereoselective. Predict the product for the following reaction.

1,2-dimethylcyclopentene + Cl2

15.05.43 Reactions of Alkenes

Hydrocarbon A, C5H8, reacts with 2 moles of Br2 to give 1,2,3,4-tetrabromo-2-methylbutane. What is the structure of hydrocarbon A? There may be more than one answer.

15.05.44 Reactions of Alkenes

Select the products that would be formed when 2-methylpropan-2-ol is subjected to acid-catalyzed dehydration. If more than one product would be formed, designate the compound that would be the major product. (Neglect cis-trans isomerism.)

The product(s) is(are):

The major product is:
(if there is only one product, select it)

15.05.45 Reactions of Alkenes

Farnesene (below) is a compound found in the waxy coating of apples.


What is the structure of the compound formed when farnesene is allowed to react
with excess hydrogen in the presence of a platinum catalyst?

What is the IUPAC name for the product of part (a)?

15.05.46 Reactions of Alkenes

What will be the outcome of the reaction shown below:

No reaction



This question was contributed by the University of Adelaide.
15.05.47 Animation Question 1

Watch the animation below about catalysis and the hydrogenation of ethylene and then answer the following questions.

Click here to watch the animation

As shown in the animation, what is the first step in catalytic hydrogenation?

Breaking the C=C bond of ethylene

Breaking a C-H bond of ethylene

Adsorption of H2 onto the catalyst surface

Adding H2 directly to the C=C bond of ethylene

Hydrogenation is formally a/an reaction.

Hydrogenation is usually carried out using what type of metal catalysts

Syn-addition of hydrogen atoms to the double bond is the usual result of hydrogenation.

The animation shows the hydrogenation of an alkene. Can alkynes also be hydrogenated in a similar way?

How many moles of hydrogen would be required to completely hydrogenate one mole of hepta-1,3-dien-5-yne?

15.06.01 Reactions of Alkynes

Starting with ethyne synthesize (Z)-hex-2-ene (enter the number of the reagents that is necessary for preparation (Z)-hex-2-ene).

1)  NaNH2

2)  methyl chloride

3)  propyl chloride

4)   H2/Ni2B (P-2)

5)  n/a

6)  ethyl chloride

7)  H2SO4/Pt

8)  ethyl alcohol




Step 1   =      Step 2  =     Step 3   =      Step 4   =     Step 5   =     

15.07.01 Aromatic Compounds

Which of the following are true statements about transition states and reaction intermediates (more than one answer is possible)?

a transition state is at an energy maximum and an intermediate is at an energy minimum.

a transition state may, although rarely, be isolated.

reactions always proceed through an intermediate.

reactions always proceed through a transition state.

15.07.02 Aromatic Compounds

Using bond line formula, draw all possible structures for tribromobenzene.

15.07.03 Aromatic Compounds

Select structural formula and give acceptable name for representative of isomer of C6H5-C4H9:

Structural formula is













Acceptable name is

15.07.04 Aromatic Compounds

Which of the following structures represent equivalent resonance structures for pyridine?

15.07.05 Aromatic Compounds

Name this compound:


15.07.06 Aromatic Compounds

Name this compound:


15.07.07 Aromatic Compounds

Name this compound:


15.07.08 Aromatic Compounds

Name this compound:


15.07.12 Aromatic Compounds

On the aromatic ring shown, is the substituent an ortho, para-director or a meta-director?
                       



15.07.13 Aromatic Compounds

On the aromatic ring shown, is the substituent an ortho, para-director or a meta-director?
                       



15.07.14 Aromatic Compounds

On the aromatic ring shown, is the substituent an ortho, para-director or a meta-director?
                       



15.07.15 Aromatic Compounds

Using bond line formula, draw p-nitroaniline.

15.07.16 Aromatic Compounds

Draw structural formula for benzene.

How many different dibromobenzenes are there? Show structures.

15.07.17 Aromatic Compounds

Draw structural formula for toluene.

How many different tribromobenzenes are there? Show structures.

15.07.18 Aromatic Compounds

Draw structural formula for benzoic acid.

15.07.19 Aromatic Compounds

Draw structural formula for aniline.

15.07.20 Aromatic Compounds

Draw structural formula for ethylbenzene.

15.07.21 Aromatic Compounds

Draw structural formula for 1,3,5-tribromobenzene.

15.08.07 Reactions Aromatic

Which of the following compounds are aromatic?

15.08.08 Reactions Aromatic

Which of the following reagents will convert benzene to isopropylbenzene?

15.08.09 Reactions Aromatic

What is(are) the product(s) of the following reaction? For this problem assume monochlorination conditions.

15.08.10 Reactions Aromatic

What is(are) the product(s) of the following reaction?

15.08.11 Reactions Aromatic

What is(are) the product(s) of the following reaction?

15.08.12 Reactions Aromatic.

What is(are) the product(s) of the following reaction?

15.08.13 Reactions Aromatic

What is(are) the product(s) of the following reaction?

15.08.14 Reactions Aromatic

What is(are) the product(s) of the following reaction?

15.08.15 Reactions Aromatic

What is(are) the product(s) of the following reaction?

15.08.16 Reactions Aromatic

What is(are) the product(s) of the following reaction?

15.08.17 Reactions Aromatic

Draw the major product (or products) that would be obtained when ethylbenzene is subjected to ring chlorination with Cl2 and FeCl3.

15.08.18 Reactions Aromatic

Draw the major product (or products) that would be obtained when anisole (C6H5OCH3) subjected to ring chlorination with Cl2 and FeCl3.

15.08.19 Reactions Aromatic

Draw the major product (or products) that would be obtained when fluorobenzene is subjected to ring chlorination with Cl2 and FeCl3.

15.08.20 Reactions Aromatic

Draw the major product (or products) that would be obtained when benzoic acid is subjected to ring chlorination with Cl2 and FeCl3.

15.08.21 Reactions Aromatic

Draw the major product (or products) that would be obtained when nitrobenzene is subjected to ring chlorination with Cl2 and FeCl3.

15.08.22 Reactions Aromatic

Draw the major product (or products) that would be obtained when chlorobenzene is subjected to ring chlorination with Cl2 and FeCl3.

15.08.23 Reactions Aromatic

Draw the major product (or products) that would be obtained when biphenyl (C6H5-C6H5) is subjected to ring chlorination with Cl2 and FeCl3.