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Chapter 1

1 C Methyl 5 C Pently 9 C nonane

2 C Ethyl 6 C Hexly 10 C Decane

3 C Propyl 7 C Heptyl 11 C Undecane

4 C Butly 8 C Octyl 12 C Dodecane

List as many constitutional Isomers for C4H10O

Draw the resonace structure

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Chapter 2

Acids are proton donor

Bases are proton acceptors

Complete the following acid-base rxn. Determine which side equillibrium favors.

Chapter 3

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Identify the functional groups in Glutathione

Chapter 4

Nomanclature

Write the Newman Projection

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Chapter 5

Draw all possible stereoisomers and label pairs of enamtiomers and diasteriomers

Champter 6

Negative things go to positive thigs OH is a bad LG Don’t be ashamed to count your carbons Watch for Hyrdride/ Methyl Shift

Substitution rxn

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Fill in the missing reagents (Multiple answers)

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Devise a synthesis of each compound from the indicated strating material ( 2 steps)

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MASS SPECTROSCOPY

Identifies molecular formula and weight of compound

Find M+ using m/z (Mass to Charge ratio)

o Z typically = +1, so m/z is equal to the mass of the compound

m/z trends:

-A compound with an odd number of N atoms gives an odd molecular ion.

-A compound with an even number of N atoms (including zero) gives an even molecular ion.

M+1 peak used for 13C

Cl presents 2 peaks (M+ and M+2) in a 3:1 ratio of 35Cl : 37Cl

Br presents 2 peaks (M+ and M+2) in a 1:1 ratio of 79Br : 81Br

IR SPECTROSCOPY

Identifies functional groups

Measured unit: cm-

NMR SPECTROSCOPY

Identifies C____H framework of compound

Uses radio waves

Measured unit: ppm

2 Types:o HNMR

Detects 1H

o CNMR Detects13C

4 features providing information on compound’s structure:

o # of signalso Position of signalso Intensity of signalo Spin-Spin splitting

Low e- density deshielding downfield

High e- densityshielding upfield

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Source material:

Smith, J. G., & Vollmer-Snarr, H. R. (2018). Organic chemistry with biological topics. New York, NY: McGraw-Hill Education.

Eubanks, I. D., & Eubanks, L. T. (2002). Preparing for your ACS examination in organic chemistry: The official guide. Clemson, SC: Examinations Institute, American Chemical Society, Division of Chemical Education.