High Yield Organic Chemistry Concepts

Which of the following functional groups would exhibit a sharp, strong absorption at approximately $1700 \text{ cm}^{-1}$ in an IR spectrum?

Considering only intermolecular forces, which compound would you expect to have the highest boiling point?

Which of the following reagents would selectively reduce a carboxylic acid to an alcohol?

What type of solvent is most suitable for an SN2 reaction?

Which of the following conditions would favor an E2 elimination reaction?

Which of the following compounds is the strongest acid?

What is the predicted major product when 2-methyl-2-butanol reacts with concentrated sulfuric acid and heat?

Which of the following reactions will result in an inversion of stereochemistry at the reaction center?

A chemist observes a broad signal around 3300 cm⁻¹ in the IR spectrum of an unknown compound. Which functional group is most likely present?

In a proton NMR spectrum, which type of proton would you expect to be the most downfield (highest ppm)?

Which of the processes listed will convert a primary alcohol into an aldehyde?

How does the addition of an electron-withdrawing group to a carboxylic acid affect its acidity?

Arrange the following functional groups in order of decreasing priority according to IUPAC nomenclature rules: Alcohol, Aldehyde, Carboxylic Acid, Ketone.

Which of the following statements accurately describes the relative reactivity of primary, secondary, and tertiary alkyl halides in SN1 reactions?

What spectroscopic feature is most useful for distinguishing between an aldehyde and a ketone?

If you react 2-butanol with H₂SO₄ and heat, what is the major product?

Which functional groups contain a carbonyl (C=O) group?

Which of the functional groups would have the highest boiling point due to hydrogen bonding and higher molar mass?

What would you expect to be true if you have a higher concentration of a strong base in an elimination reaction?

Which of the compounds listed when reacted with $NaOH$ becomes deprotonated?

Which of the following spectroscopic techniques would be most useful for identifying the presence of a carbonyl group in an unknown organic compound?

What is the role of a polar protic solvent in an SN1 reaction?

How does the presence of a bulky base, such as potassium tert-butoxide (KOtBu), affect the product distribution in reactions with alkyl halides?

A compound shows a sharp signal at 3300 cm⁻¹ in its IR spectrum. What functional group is likely present?

Which reagent is appropriate to transform a secondary alcohol into a ketone?

How would you expect the acidity of phenol to change if a nitro group (-NO₂) is added to the para position?

What is the function of DMSO as a solvent in SN2 reactions?

Under what conditions will a primary alcohol be readily oxidized to a carboxylic acid?

Which of the following will have the highest chemical shift in $^1H$ NMR?

What is the major organic product when 2-pentanol is treated with pyridinium chlorochromate (PCC)?

Which set of reactants will produce ethyl propanoate via a Fischer esterification?

Which of the following reagents is best suited to oxidize cyclohexanol to cyclohexanone?

A chemist wants to synthesize methyl benzoate. Which set of reactants and conditions should they use?

What starting material and reagent would you use to synthesize 3-methyl-2-butanone?

An unknown compound reacts with acidified ethanol to produce a sweet-smelling liquid and water. The unknown compound is most likely which of the following?

Which reaction will result in the formation of ethyl acetate?

What alcohol and what reagent will produce butanone?

A reaction between butanoic acid and methanol is catalyzed by sulfuric acid. What is the organic product?

Which of the following alcohols, when oxidized with Jones reagent, will produce a ketone?