Organic Chemistry MT1: Acid-Base, Resonance, and Conformations

What is the Brønsted-Lowry definition of acids and bases?

An acid is a proton donor, while a base is a proton acceptor.

What does the Lewis theory state about acids and bases?

A Lewis acid is an electron-pair acceptor, and a Lewis base is an electron-pair donor.

What is the ARIO order used for?

It is used to predict acid strength based on Atom, Resonance, Induction, and Orbital factors.

How does hybridization affect acidity?

More s character in the hybrid orbital means the hydrogen is held closer to the nucleus, increasing acidity.

What is the leveling effect in acid-base chemistry?

It dictates that the strongest base present cannot be stronger than the conjugate base of the solvent.

What are constitutional isomers?

Compounds with the same chemical formula but different connectivity of atoms.

What is the difference between polar and nonpolar covalent bonds?

Polar covalent bonds have an electronegativity difference greater than 0.5 but less than 1.7; nonpolar bonds have a difference less than 0.5.

What is the significance of resonance structures?

Resonance structures represent different ways of arranging electrons in a molecule, affecting stability and reactivity.

What is the relationship between molecular mass and boiling points?

Higher molecular mass generally leads to higher boiling points, except when hydrogen bonding is present.

What is the role of intermolecular forces in boiling points?

Stronger intermolecular forces result in higher boiling points.

What is torsional strain?

The energy difference between staggered and eclipsed conformations due to unfavorable bonding orbital and anti bonding orbital interactions

What is steric strain?

The repulsion between electron clouds of larger groups in close proximity.

What is the difference between staggered and eclipsed conformations?

Staggered conformations have groups positioned to minimize torsional strain, while eclipsed conformations have groups aligned, increasing strain.

What are the characteristics of cyclohexane's chair conformation?

It has no torsional strain and allows for equatorial and axial positioning of substituents.

What is the significance of substituent position in chair conformations?

Substituents in equatorial positions are lower in energy and more stable than those in axial positions.

What does the term 'cis' signify in cyclic compounds?

Cis indicates that two substituents are on the same side of the ring.

What does the term 'trans' signify in cyclic compounds?

Trans indicates that two substituents are on opposite sides of the ring.

What is the hybridization of nitrogen in an amide?

The nitrogen is sp2 hybridized and trigonal planar due to resonance participation.

What is the effect of branching on boiling and melting points?

Less branching leads to higher boiling and melting points due to decreased steric hindrance.

What is the significance of the pKa value in acid-base reactions?

The equilibrium favors the formation of the weaker acid, which has a higher pKa value.

What is the relationship between electronegativity and acidity?

More electronegative atoms stabilize negative charges in conjugate bases, increasing acidity.

What is the role of electron delocalization in acidity?

Electron delocalization spreads out charge over multiple atoms, stabilizing the conjugate base and increasing acidity.

What is the significance of curved arrows in resonance structures?

Curved arrows indicate the movement of electrons and do not represent real physical processes.

What is the difference between a single, double, and triple bond?

A single bond has one σ bond, a double bond has one σ and one π bond, and a triple bond has one σ and two π bonds.

What is a bicycloalkane?

A compound with two interconnected rings in its structure.

What is the significance of the anti conformation?

The anti conformation has a dihedral angle of 180° and represents the lowest energy conformation.