Organic Chemistry Exam 2

Acid-Base Reactions

100

What is the definition of a Bronsted Lowry acid?

Donator of protons

200

What is the conjugate base of carboxylic acid?

Carboxylate 

300

What way does the following reaction proceed?

CH₃CH₂O^- + H₂O <-> CH₃CH₂OH + OH^-

Forward

400

Prove if water is a suitable acid to protonate phenoxide. Explain why or why not  

is not suitable because of pka

500

Finish the following reaction and label the acid, base, conjugate acid, conjugate base, and determine the direction.

CH₃COCH₂COCH₃ + H₂O <-> 

CH₃COCH₂COCH₃ + H₂O <-> H₃O⁺ + CH₃COCHCOCH₃^-

A, B, CA, CB

Reverse

Structures

100

What is the molecular formula of pentane?

C₅H₁₂

200

Draw the following, 4-ethyl-2,4-dimethyl-heptane

will draw on board

300

Draw the following, 1,3-dimethyl-5-isopropyl-cyclohexane

will draw on board

400

Draw the most stable Newman configuration of 2-methyl-butane (looking down the bond between carbon 2 and 3)

will draw on board, should be staggered

500

draw chairs of trans-1,2-dimethyl-cyclohexane and cis-1,2-dimethyl-cyclohexane. Which is more stable?

will draw on board, trans equilateral is most stable

Random

100

what is the hybridization of a carbocation

sp2

200

Draw nitrogen and 3 carbons with a negative charge, add hydrogens as necessary

will draw on board, can have multiple answers

300

What is the molecular geometry of (CH₃)₂CO?

Trigonal Planar 

400

What kind of isomer is shown when a bond is rotated

Conformational isomer

500

how many carbons are in methylcyclopentane?

6 

Nomenclature

100

What is a structure called when there are two substituents facing the same way

Cis

200

What are the steps to naming? 

Find the parent (longest chain), name substituents, find the location of the substituents. Put together with substituents in alphabetical order and the parent named last. 

300

What is the IUPAC name of the following,

CH₃-CH-CH₃

       CH₃

methylpropane

400

What are the following numbers in terms of chemistry (IUPAC)

6-2-8-7-9-10-4-1-3-5

hex-eth-oct-hept-non-dec-but-meth-prop-pent

500

Name the following,

(CH₃)₂CHCH₂CHCH₂CH₃CH₂CH₃

2-methyl-4-ethylhexane

Resonance

100

What is resonance?

The movement of electrons

200

What can you not do when doing resonance? 

break sigma bonds and break octet

300

How can resonance help with deciding if an acid is strong?

If the CB can resonate then the acid is strong

400

Draw all resonance structures of CO₂

will draw on board, should be 3 total structures

500

Draw all the resonance structures of Acrylic Acid (CH₂CHCOOH) and label from best to worse

will draw on board, there should be 4 structures total