Jeopardy! Chapters 1-4.10

Chapter 1 (misc.)

100

How do you calculate formal charge on an atom?

Formal charge = # valence electrons - # "owned"

owned = 1 electron for bonds, 2 electrons for lone pairs

200

Draw a resonance structure for 

-OCH=CH2 

(draw on board)

(on board)

300

What is the difference between a resonance structure and isomers?

Resonance structures: different ways of drawing the exact same molecule, just electrons moving around

Isomers: completely different molecules that just happen to share the same chemical formula

400

Convert to a skeletal structure:

(CH3)2CHCH(NH2)CO2H

(draw)

(draw)

500

Sketch the sigma bond orbitals for CH4 AND indicate the hybridization of each.

H = s

CH = sp3

Chapter 2: acid-base chemsitry

100

Acids are proton-_______.

donors

200

What are the 4 factors that determine acid strength? List them in order of importance.

Atom (EN element with H-bonded to it)

Resonance (more resonance)

Hybridization (greater s-character)

Inductive effects (ewgs)

300

Draw the acid-base reaction between acetone and ethoxide, labeling the acid, base, conjugate acid, and conjugate base.

(draw on board, and it's in the notes)

400

Draw the Lewis acid-base reaction mechanism between CH3OCH3 and BF3 (draw on board). Label accordingly.

CH3OCH3 = Lewis base (electron donor), nucleophile

BF3 = Lewis ACid (electron ACceptor), electrophile

500

Which is the strongest acid? (draw!)

A) CH3COOH

B) CF3COOH

C) CF3CH2OH

B) CF3COOH

Chapter 3: Organic functional groups

100

What is this? Drawing it may help.

RCOOR

Ester

200

What is the difference between a primary, secondary, and tertiary amine?

Primary = connected to 1 R-group, R-NH2

Secondary = 2 R-groups, R-NH-R

Tertiary = 3 R-groups, R3N

300

What is the difference between melting point and boiling point trends in organic molecules?

Branching can sometimes lead to higher melting point if it makes the molecule more compact, whereas for bp branching lowers bp.

Type/strength of bond matters for both.

400

Which compound has the highest solubility in H2O?

A) CH3CH2CH2CH2CH3

B) CH3CH2CH2CH2COOK

C) CH3CH2CH2CH2COOH

D) CH3CH2CH2CH2COCH3

B) CH3CH2CH2CH2COOK

(ionic bonds dissociate better)

500

How can you determine if a molecule can hydrogen-bond to itself?

It has H-bond donors (H-N or H-O) AND acceptors (lone pair).

Chapter 4: Alkanes

100

Draw butane and cyclobutane.

4 carbons

200

What is the difference between steric, torsional, and angle strain?

Angle strain comes from squeezing or stretching bond angles away from their ideal shape

torsional strain happens when bonds are forced to line up directly behind each other (conTORT, eclipsed)

steric strain happens when large groups bump into each other in space because they are too crowded, electron cloud repulsion

300

DEGREES OF UNSATURATION DAILY DOUBLE!

Draw 4 constitutional isomers of C7H14.

u = 1 so 1 ring or 1 double bond

400

Draw four Newman projections for 1,2-dichloroethane (Cl–CH2–CH2–Cl), rotating 60 degrees each projection. Label the gauche conformer.

(draw)

Gauche is any 60 degree conformer.

500

Draw an energy diagram for the 1,2-dichloroethane (Cl–CH2–CH2–Cl) conformations you drew. 

Highest Energy = 40 kJ/mol, Lowest= 0 kJ/mol

Intermediates = 20 kJ/mol and 6 kJ/mol

(draw)

anti = 0 kJ/mol (180 degrees)

eclipsed Cl/Cl = 40 kJ/mol

gauche = 6 kJ/mol (Cls further from each other) and 20 kJ/mol (Cls closer)