Outline of Course Objectives and Final Exam, Chemistry 247B, Hanson, Fall 2007


Numbers in parentheses relate to the relative importance of this area.
They may or may not correspond exactly to the number of points on the
test in this area, as some problems may relate to more than one area.
It's a sure bet that only a fraction of this will be on the final exam. 
Still, it would be a good idea to review all these areas, identify
your own strengths and weaknesses, and work on those areas that still
seem a bit foggy. You may find that some of these areas are much more
understandable now than when you first looked at them. That shows you
have really learned something! Hopefully, this exam will give you a
good opportunity to demonstrate what you've learned in organic chemistry.

(15) Nomenclature:

 We looked specifically at the way to name:

	alkanes
	alkenes and alkynes
	alkyl halides and ethers
	alcohols and amines

 You should be prepared to:

	identify and name the parent chain
	identify and name functional groups
	identify and name substituents
	use correct numbering for locating functional groups
	use correct numbering for locating substituents
	properly identify stereochemistry (E, Z, R, S, cis, trans)

(15) Structure

 We talked about:

	sigma and pi bonding
	electronic effects on pKa
	effect of structure on boiling points
	effect of structure on solubility
	conformations of alkanes
	conformations of cyclohexanes
	enantiomers and diastereomers
	optical rotation
	electron delocalization

 You should be prepared to:

	draw proper Kekule structure
	identify sp, sp2, and sp3 carbons
	use Newmann projections to describe conformations
	draw and identify cyclohexane equatorial and axial groups		
	identify and draw the lowest-energy conformation of a compound
	draw proper resonance contributors
	describe how to separate a mixture of compounds
	rank compounds in order of boiling point based on structure
	rank compounds in order of solubility in water based on structure
	identify enantiomers and diastereomers
	use optical rotation as an indicator of enantiomer ratios	

(20) Spectroscopy

 We talked about:

	nuclear magnetic resonance spectroscopy (NMR)
	  NMR chemical shift
	  NMR chemical and magnetic equivalence
	  NMR coupling and splitting patterns
	  common 1H and 13C experiments
	infrared spectroscopy (IR)
	  IR and functional groups
	  IR "fingerprints"
	mass spectrometry (MS)
	  the molecular ion
	  isotope patterns
	  fragmentation
	combined spectroscopy
	  evidence of a chemical structure
	  deducing an unknown chemical structure

 You should be able (with tables of characteristic NMR and IR data available) to:

	identify the peaks in an NMR spectrum
	explain the splitting observed in an NMR spectrum
	explain the major absorptions in an IR spectrum
	predict the rough NMR spectrum of a simple (one- or two-functional group) compound
	determine a chemical structure using combined NMR, IR, and MS data

(25) Mechanism and Theory

 We talked about:

	Markovnikov's rule
	rearrangements of cations
	molecular orbital (MO) theory
	the reactivity-selectivity principle
	thermodynamic vs. kinetic control
	mechanisms of substitution and elimination
	Zaitsev's rule
	radical chain reactions

 You should be prepared to:

	write simple mechanisms for reactions involving 1-3 steps
	explain why one product is favored over another in specific cases
	explain the role of temperature in chemical reactions
	discuss initiation, propagation, and termination
	discuss molecules and reactions in terms of interacting orbitals
	discuss the role of various effects on substitution and elimination

(25) Reactions

 We talked about:

	electrophilic addition to double bonds
	hydrogenation of alkenes and alkynes
	substitution and elimination reactions
	radical chain reactions of alkanes and alkenes
	
 You should be prepared to:

	predict the major product of a reaction
	describe conditions that will convert a specific reactant to a specific product
	
(20) Synthesis

 We talked about:

	retrosynthetic planning and brainstorming
	issues of regioselectivity and stereoselectivity
	issues involving rearrangements of carbocations
	methods of forming carbon-carbon bonds
	use of organometallic compounds for synthesis
	the central role of alkenes in synthesis
	methods of "activating" alcohols toward substitution and elimination

 You should be prepared to:

	discuss the range of possible reactions of a given compound
	discuss the range of possible reactions leading to a given compound
	design a short synthesis from a specific starting material to a specific target compound
	design a short synthesis of a target compound from "any compounds with fewer than N carbons"
	discuss issues of regioselectivity and stereoselectivity in relation to your design
	design two or more syntheses having the same goal and critically compare them