ALL PRACTICE

In which structure(s) below does the oxygen have a formal charge of +1?

Which of the following represent a pair of constitutional isomers?

Which of the following species is/are a resonance form(s) of the species in the box?

How many s-sp² bonds are there in the following substance?

Which compound would have the highest boiling point?

CH₃CH₂CH₂CH₂CH₂CH₃

 CH₃CH₂OCH₂CH₂CH₃

 CH₃CH₂CH₂CH₂CH₂OH

 CH₃CH₂OCH(CH₃) ₂

 CH₃OCH₂CH₂CH₂CH₃

For the functional group(s) on the following molecule what characteristic IR absorption(s) would be expected (ignoring C-H absorptions)?  a peak around 1700 cm^-1

  a peak around 3300 cm^-1

  a peak around 1650 cm^-1

  a peak around 2250 cm^-1

The IR stretching frequency can be predicted to occur at the highest frequency for which of these bonds?

  C–H

  C–F

  C–Cl

  C–Br

  C–I

In the following reaction which chemical species is acting like a nucleophile?

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

Which acid-base reaction would not take place as written?

  CH₃Li + CH₃CH₂CH₂CH₂NH₂ ⎯⎯⎯⎯→ CH₄ + CH₃CH₂CH₂CH₂NHLi

CH₃C≡CH + NaOCH₃ ⎯⎯⎯⎯→ HC≡CNa + CH₃OH

  HC≡CNa + H₂O ⎯⎯⎯⎯→ HC≡CH + NaOH

  CH₃OH + NaNH₂ ⎯⎯⎯⎯→ CH₃ONa + NH₃

  CH₃CO₂H + CH₃ONa ⎯⎯⎯⎯→ CH₃CO₂Na + CH₃OH

The IUPAC name for this is:

6-Ethyl-3,4-dimethylheptane

  2-Ethyl-4,5-dimethylheptane

  3,4,6-Trimethyloctane

  3,5,6-Trimethyloctane

  2-(1-Methylpropyl)-4-methylhexane

Provide a name for the following compound:

2-Bromo-4-chloro-4-isopropylpentane

  4-Bromo-2-chloro-2-isopropylpentane

  5-Bromo-3-chloro-2,3-dimethylhexane

  2-Bromo-4-chloro-4,5-dimethylhexane

  2-(2-Bromopropyl)-2-chloro-3-methylbutane

A correct name for the following compound is:

4-bromo-3,8-dimethylbicyclo[5.2.2]nonane

  3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane

  4-bromo-3,8-dimethylbicyclo[5.2.1]decane

  7-bromo-2,6-dimethylbicyclo[5.2.0]nonane

  4-bromo-3,8-dimethylbicyclo[5.2.0]nonane

trans-1,2-Dibromocyclohexane is represented by structure(s):

What is the index of hydrogen deficiency (or degree of unsaturation) for the drug lidocain?

3

4

5

6

7

What is IUPAC name of the following compound?

(R) -2-methyl-3-butyn-1-ol

 (S) -2-methyl-3-butyn-1-ol

 (R) -2-methyl-1-butyn-3-ol

 (S) -2-methyl-1-butyn-3-ol

Which of the following is (are) meso compound(s) ?

I and II are:

constitutional isomers.

enantiomers.

identical.

diastereomers.

not isomeric.

The molecules shown are:

  constitutional isomers.

  enantiomers.

  diastereomers.

  identical.

  None of these choices.

Which alkyl chloride, though primary, is essentially unreactive in S_N2 reactions?

Which alkyl halide would you expect to react most slowly when heated in aqueous solution?

  (CH₃)₃C-F

  (CH₃)₃C-Cl

  (CH₃)₃C-Br

  (CH₃)₃C-I

  All of these choices would react at the same rate.

Which S_N2 reaction will occur most rapidly in aqueous acetone solution? Assume concentrations and temperature are the same in each instance.

HO^- + CH₃-Cl ⎯⎯⎯⎯→ CH₃OH + Cl^-

HO^- + CH₃CH₂-Cl ⎯⎯⎯⎯→ CH₃CH₂OH + Cl^-

HO^- + (CH₃)₂CH-Cl ⎯⎯⎯⎯→ (CH₃)₂CHOH +Cl^-

HO^- + (CH₃)₃C-Cl ⎯⎯⎯⎯→ (CH₃)₃COH + Cl^-

HO^- + (CH₃)₃CCH₂-Cl ⎯⎯⎯⎯→ (CH₃)₃CCH₂OH + Cl^-

Name the following compound:

  (S,E)-2,4-dibromo-3-methylpent-2-ene

  (R,Z)-2,4-dibromo-3-methylpent-2-ene

  (R,E)-2,4-dibromo-3-methylpent-3-ene

  (S,E)-2,4-dibromo-3-methylpent-3-ene

  (R,E)-2,4-dibromo-3-methylpent-2-ene

What is the major product for the following reaction?

Which alkene would you expect to be the major product of the following dehydration?

Which reaction conditions would not yield 2-butyne from 1-propyne?

What is the major product for the following reaction?

What is the major product for the following reaction?

What is the major product for the following reaction?

What is the major product for the following reaction?

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow?

  1.00 ppm, quartet

  2.40 ppm, singlet

  2.40 ppm, quartet

  3.00 ppm, quartet

  2.40 ppm, triplet

For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

How many chemically distinct ¹H NMR signals are there in the following compound?

Consider the expected ¹H NMR spectrum of 1,1,3,3-tetramethylcyclopentane. Which of the following is likely to be observed?

7 signals: all singlets

7 signals: 4 singlets, 3 doublets

3 signals: all singlets

3 signals: 1 singlet, 2 doublets

3 signals: 2 singlets,1 doublet

The ¹H NMR spectrum of which of the compounds below, all of formula C₇H₁₂O₂, would consist of three singlets only?

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₈H₁₄? Relative integration is shown.

A compound with the molecular formula C₈H₉BrO gave the following ¹H NMR spectrum:triplet, δ 1.4quartet, δ 3.9multiplet, δ 7.0 (4H)There was no evidence of an -OH band in the IR spectrum. A possible structure for the compound is:

In the structure shown, H_a and H_b are classified as:

  homotopic protons.

  vicinal protons.

  enantiotopic protons.

  diastereotopic protons.

  isomeric protons.

Mono-bromination of the following alkane (using Br₂ with light) would give?

Which compound below would give rise to 4 signals in the proton NMR spectrum and 6 signals in the carbon NMR spectrum? (Assume you can separate and see all peaks.)

What is the correct IUPAC name for the following compound?

3-methyl-4-ethyl-3-hexen-6-ol

4-ethyl-3-methyl-3,6-hexenol

3-ethyl-4-methyl-3-hexen-1-ol

3-methyl-4-(2-

hydroxyethyl)-3-hexene

3-(2-hydroxyethyl)- 3-methyl-3-hexene

Which compound would have the greatest solubility in water?

  Diethyl ether

  Methyl propyl ether

  1-Butanol

  1,2-Butanediol

  Pentane

Which product(s) would you expect to obtain from the following sequence of reactions?

The reaction between 1-pentanol and HBr to yield 1-bromopentanol is probably:

  an S_N1-type reaction involving the protonated alcohol as the substrate.

  an S_N2-type reaction involving the protonated alcohol as the substrate.

  an E1-type reaction involving the protonated alcohol as the substrate.

  an E2-type reaction involving the protonated alcohol as the substrate.

Which of the following could be used to synthesize 2-chlorobutane?

If trans-2-bromocyclohexanol is treated with sodium hydroxide what is the major product?

The most stable conformation of cis-1-tert-butyl-2-methylcyclohexane is the one in which:

  the tert-butyl group is axial and the methyl group is equatorial in a chair conformation.

  the methyl group is axial and the tert-butyl group is equatorial in a chair conformation.

  both groups are axial in a chair conformation.

  both groups are equatorial in a chair conformation.

  the twist boat conformation is adopted.

What is the major product formed after treating the following molecule with excess H₂ in the presence of Pd/C catalyst?

  cis-2-penten-5-ol

  1-pentanol

  pentane

  none of these choices

Which would be the major product of the following reaction sequence?

A compound, C₆H₁₀, which reacts with 2 mol of hydrogen over a platinum catalyst and which shows an IR absorption band at approximately 3300 cm^-1 could be:

What is the major product for the following reaction sequence?

Which of the following could be used as the basis for a simple test that would distinguish between 1-pentyne and pentane?

  IR examination

  Br₂/CCl₄

  KMnO₄/H₂O

  Two of these choices.

  All of these choices.

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₁₂H₁₇NO and a characteristic IR stretch near 1700 cm^-1 and a characteristic peak in the ¹³C-NMR at 170 ppm? Relative integration is shown.

In general, when the addition of an unsymmetrical electrophilic reagent to an unsymmetrical alkene forms the product predicted by Markovnikov's rule, that occurs because:

  the product is statistically favored.

  steric hindrance favors its formation.

  it is formed via the more/most stable carbocation.

  it is the more/most stable product.

  All of these choices are reasons.

Consider the reaction of 2-chloro-2-methylpentane with sodium iodide.Assuming no other changes, how would it affect the rate if one simultaneously doubled the concentration of 2-chloro-2-methylpentane and sodium iodide?

It would quadruple the rate.

No effect.

It would double the rate.

It would increase the rate five times.

It would triple the rate.

Which of the following alkyl bromide isomers would most readily undergo an S_N2 reaction?

4-bromo-1-butene

3-bromo-1-butene

All will react at the same rate.

bromocyclobutane

1-bromo-1-butene

Which of the following solvents will best promote a nucleophilic reaction between NaCN and 1-bromopropane?

HF(aq)

running with no solvent

MeCN

H₂O/MeOH mixture

H₂O

What would be the major product of the following reaction?

S_N1 reactions of the following type:Nu:^- + R-X ⎯⎯⎯⎯→ R-Nu + :X^-are favored

by use of a weak nucleophile.

by increasing the polarity of the solvent.

by the use of tertiary substrates (as opposed to primary or secondary substrates) and by use of a weak nucleophile.

by the use of tertiary substrates (as opposed to primary or secondary substrates).

by increasing the concentration of the nucleophile.

The product(s) for the following reaction would mainly be dictated by which mechanism?

E1

S_N1

S_N2

E2

Name the following compound:

(R,Z)-5-benzyloct-5-en-3-ol

(R,E)-5-benzyloct-3-en-6-ol

(R,Z)-5-phenyloct-5-en-3-ol

(R,E)-5-phenyloct-5-en-3-ol

(R,E)-5-benzyloct-5-en-3-ol

Which molecule would have the lowest heat of hydrogenation?

Which product(s) would be produced by acid-catalyzed dehydration of 2-methyl-2-pentanol?

Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?

Treating 1-methylcyclohexene with H₃O⁺ would yield primarily which of these?

Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would:

be a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial.

be a pair of diastereomers and, in their most stable conformation, one would have the bromines equatorial and axial, and the other would have the bromines equatorial and equatorial.

be a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial.

be a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial.

be a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial.

The reaction of BrCl (bromine monochloride) with 1-methylcyclopentene will produce which of the following as the predominant product:

What is the major product for the following reaction?

Which reagent(s) given below could be used to synthesize cis-1,2-cycloheptanediol from cycloheptene?

H₂SO₄, heat

KMnO₄, OH⁻, 5^oC

None of these choices.

KMnO₄, H₃O⁺, 75^oC

All of these choices.

What is the major product of the following reaction sequence?

What is the major product for the following reaction?

What is the major product for the following reaction?

Which ion is the strongest nucleophile in an aprotic solvent such as dimethylsulfoxide?

F^-

I^-

Cl^-

Br^-

All of these choices are equal.

Which of the following is not a good leaving group?

I⁻

Cl⁻

C₂H₅O⁻

CH₃CO₂⁻

All of these choices are good leaving groups.

What is the major product for the following reaction?

What is the major product for the following reaction?

What is the major product for the following reaction sequence?

What is the major product for the following reaction?

What is the simplest alkane, i.e., the one with the smallest molecular weight, which possesses primary, secondary and tertiary carbon atoms?

2-Methylpropane

2-Methylbutane

2-Methylpentane

3-Methylpentane

2,2-Dimethylbutane

An IUPAC name for this is: 

5-Methyl-4-(1-methylpropyl)hexane

2-Methyl-3-(1-methylpropyl)hexane

2-Methyl-3-(2-methylpropyl)hexane

3-Methyl-4-(1-methylethyl)heptane

5-Methyl-4-(1-methylethyl)heptane

Neglecting stereochemistry, which of these common group names is ambiguous, i.e., does not refer to one specific group?

Butyl

sec-Butyl

tert-Pentyl

Neopentyl

sec-Pentyl

How many compounds with the formula C₇H₁₆ (heptanes) contain a single 3° carbon atom?

What is the correct IUPAC name for the following compound?

5-Ethyl-3-fluorohexanol

5-Ethyl-3-fluoro-1-hexanol

2-Ethyl-4-fluoro-6-hexanol

3-Fluoro-5-methyl-7-heptanol

3-Fluoro-5-methyl-1-heptanol

The correct IUPAC name for the following compound is:

5-(1-pentanolyl)-cyclobutane

5-cyclobutyl-1-pentanol

1-cyclobutyl-5-pentanol

1-(5-pentanolyl)-cyclobutane

none of these choices

Which of the following is bicyclo[3.2.2]nonane?

What is the correct name of the following compound?

1-Chlorobicyclo[4.1.1]octane

2-Chlorobicyclo[4.1.0]octane

2-Chlorobicyclo[4.1.1]octane

2-Chlorobicyclo[4.1.1]heptane

5-Chlorobicyclo[4.1.1]octane

   A correct IUPAC name for the following compound is:

3,6,7-trimethyl-4-bromo-1-octene

4-bromo-3-methyl-6-isopropyl-1-heptene

4-bromo-3,6,7-trimethyl-1-octene

4-bromo-6-isopropyl-3-methyl-1-heptene

4-bromo-6-isopropyl-3,6-dimethyl-1-hexene

Give the IUPAC name for this

3-Methyl-4-hexyne

4-Methyl-2-hexyne

2-Ethyl-3-pentyne

4-Ethyl-2-pentyne

3-Methyl-2-hexyne

The least stable conformation of butane is:

Which conformation(s) of 1,2-dibromoethane does not illustrate one or more gauche interactions?

Which staggered Newman projection(s), looking down the C-2—C-3 bond (C-2 in front and C-3 in back), illustrates the following boxed compound?

Select the systematic name for this

cis-1,3-Dichlorocyclopentane

trans-1,4-Dichlorocyclopentane

cis-1,2-Dichlorocyclopentane

trans-1,3-Dichlorocyclopentane

1,1-Dichlorocyclopentane

Which conformation represents the most stable conformation of trans-1-bromo-4-methylcyclohexane?

Pairs of enantiomers are

(R)-2-Chlorobutane is represented by:

Which compound would show optical activity?

cis-1,4-Dimethylcyclohexane

trans-1,4-Dimethylcyclohexane

cis-1,4-Dimethylcycloheptane

trans-1,4-Dimethylcycloheptane

More than one of these choices

75% (R), 25% (S) 

25% (R), 75% (S) 

50% (R), 50% (S) 

67% (R), 33% (S)

33% (R), 67% (S) 

CH₃CHBrCH₂CHClCH₃ is the generalized representation of what number of stereoisomers?

I and II are

constitutional isomers

enantiomers

identical

diastereomers

not isomeric

Select the hybridized atomic orbital.