OCHEM

What is the major organic product of the following reaction?

I

What is the product of the following sequence of reactions?

I

Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.

I > II > IV > III

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

I only

Determine the product of the following reaction.

II

What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

II

What is the product formed by hydrolysis of the following lactone with acid?

II

Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?

II

Rank the following compounds in order of increasing acidity, putting the least acidic first.

II < I < III < IV

Rank the following compounds in order of decreasing reactivity in nucleophilic addition reactions, starting with the most reactive compound.

II > IV > I > III

From the compounds shown below, select the structure of the major product of the Mono-bromination of this alkane, , (using Br2 and light).

III

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

III

What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

III

What is the correct structure for anisole?

III

What is the major organic product of the following reaction?

III

What is the major product expected for the following reaction sequence?

III

What is the major product from the following reaction?

III

What is the product of the following reaction?

III

What product is formed when the following acetal is hydrolyzed with aqueous acid?

III

Which free radical would be MOST stable?

III

Which of the following heterocycles is not aromatic?

III

Rank the following dienophile in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

III < I < II

What is the major organic product of the following reaction?

IV

What is the major organic product of the following series of reactions?

IV

What is the major product of the following reaction?

IV

What is the structure for ethyl 4-chlorobenzoate?

IV

Which of the following compounds is aromatic?

IV

Which of the following is the most reactive diene in a Diels-Alder reaction?

IV

Which of the following reagents can accomplish the transformation below?

K 2Cr 2O 7, H 2SO 4, H 2O

What is the major organic product of the following reaction?

a mixture of I and II

What is the starting material in the reaction below?

benzyl bromide

Put the following steps in the correct order for the radical reaction with peroxide and HBr and an alkene.

see image

The compound 2-methyl-2-pentanol does not undergo oxidation by H2CrO4 because:

the intermediate chromate ester cannot lose hydrogen.

What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

triplet

Give the IUPAC name for the following compound.

(S)-4-Bromopentan-2-one

Number the compounds below from LEAST reactive (1) to MOST reactive (5) toward Nucleophilic Acyl Substitution.

- Carboxylate : 1 - Acid Chloride : 5 - Ester : 3 - Acid Anhydride : 4 - Amide : 2

Match the structure or term from the following list with each description below.

- The reactive electrophile in Friedel-Crafts acylation reactions. : R-C=O+ - The electrophile in aromatic nitration. : +NO2 - Groups which activate aromatic rings toward electrophilic substitution : electron-donating - Groups which activate aromatic rings toward nucleophilic substitution. : electron-withdrawing - Intermediate in the mechanism of electrophilic aromatic substitution. : Meisenheimer complex

Which of the reagents shown below will be most likely to give the product shown on the right given the starting materials shown on the left?

1. O3 2. H2O

Select the best reagents to perform the reaction shown below.

1. O3; 2. DMS

Given these choices, which of the following reaction conditions is the best to accomplish the following transformation?

1. OsO 4 2. NaHSO 3, H 2O

Select the best reagents to perform the reaction shown below.

1. mCPBA; 2. H3O+

What is the IUPAC name of the following compound?

2,5-Dichloroaniline

Provide the reactants necessary to prepare the following alkene using the Wittig reaction.

2-pentanone and 1-bromopropane

How many peaks would you expect to see in the 13C-NMR of the molecule below?

3

What is the IUPAC name for the following compound?

3-fluoropentanonitrile

How many possible products would be produced in the monochlorination of the alkane shown including stereoisomers?

5

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

6

Which of the following statements about the bromination of 2-methylbutane is true?

A single radical halogenation product predominates.

What is the first step in the general mechanism for electrophilic aromatic substitution?

Addition of the electrophile to the aromatic ring

Which of the following is the repeat unit for the polymer produced in the following reaction?

B

What reagents would be necessary to produce the following product from benzene?

CH 3CH 2C(O)Cl, AlCl 3 2. HNO 3, H 2SO 4 3. Zn(Hg), HCl

What is the missing reagent in the reaction below?

Diethylamine, mild acid

Which reagent can be used to reduce the alkene in cyclopent-2-enone?

H 2 and Pd-C

What reagents are necessary to perform the following reaction?

H3O + and Ethanol

What reagents would BEST accomplish the following reaction?

NH2NH2 and NaOH

What reagents are necessary to perform the following reaction?

Na, NH 3

What is the name of the general reaction type that aldehydes and ketones undergo?

Nucleophilic addition

What is the major organic product of the following reaction?

Only I

Which of the following ions is aromatic?

Only II and IV

What is the major organic product of the following reaction?

Only III

Which of the reagents shown below will most likely provide the product desired at right as the major product?

PCC

What is(are) the reagents that would produce the product shown in the reaction below?

Ph2CuLi then H2O

What is the IUPAC name for the following compound?

Phenyl propanoate

Which steps are rate determining in the mechanism of radical halogenation?

Propagation

Why is pyridine included in the reaction of an acid chloride and an amine or alcohol?

Pyridine will neutralize the acid by-product of the reaction.

Give the IUPAC name of the following compound.

R-2-methylpentanenitrile

Give the IUPAC name for the following compound.

R-3-methylcyclohexanone

What region of the electromagnetic spectrum does nuclear magnet resonance spectroscopy use?

Radio frequency

How could you synthesize an enamine?

React a ketone or an aldehyde with a secondary amine.

What is the correct classification of the following reaction?

Reduction reaction

What reagents are necessary to perform the following reaction?

SOCl 2

Which of the following statements about kinetic vs. thermodynamic products is true?

The kinetic product predominates at low temperature.

What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH 2Cl 2 is treated with aqueous NaOH solution?

The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH 2Cl 2 layer.

All of the compounds below have the formula C7H12O2. For which of these shown, would the 1H NMR spectrum consist of only two singlets?

V

The 1H-NMR signal for which of the indicated protons would occur the farthest downfield?

V

What is the product (A) of this series of reactions? Hint: You may assume that there is only one equivalent of each reagent shown.

V

What is the product of the following series of reactions?

V

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

V

Is the following reaction reversible and, if so, under what conditions would it be irreversible?

Yes, under basic conditions

What sequence of reactions is required for the following transformation?

[1] Ph 3P, [2] BuLi, [3] acetone