Chemistry Common Sense 1. Carbon can never have more than an octet of electrons surrounding it! It can have less than an octet of electrons: 7 electrons = radical intermediate 6 electrons = carbocation intermediate 2. There are NO negatively charged reactants, intermediates, or products in acidic solution. Acidic = neutral or + 3. There are NO positively charged reactants, intermediates, or products in basic solution. Basic = neutral or - 4. In electron-pushing for drawing out mechanisms, start the arrow at the electron rich site & move arrow towards the electron poor site. 5. Many organic reactions have an electrophile (electron poor reactant) and a nucleophile (electron rich reactant).

Chemistry Common Sense 6. The thermodynamic product is the most stable product. It predominates when the reaction is reversible. 7. The kinetic product is the fastest formed. It predominates when the reaction is not reversible. 8. The stronger the acid, the more readily it gives up a proton; the stronger the acid, the lower its pKa. 9. The stronger the acid, the weaker its conjugate base. 10. Acid strength depends on the stability of the base formed when the acid gives up its proton - the more stable the base, the stronger its conjugate acid.

Naturally Occurring Carboxylic Acids RCO 2 H

Naturally Occurring Carboxylic Acid Derivative s RCO 2 X

Nomenclature of Carboxylic Acids & Derivatives As we will see, a compound can contain more than one type of Functional group. What gets the higher priority? What if a functionality isn’t the highest priority? Use the table below. Functional GroupSuffix if highest priority groupAs a substituent CO 2 H carboxylic acid-oic acid-carboxy- CO 2 R ester-oate-alkoxycarbonyl- CO 2 NR 2 amide-amide-carbamoyl- CHO aldehyde-al-oxo- CRO ketone-one-oxo- OH alcohol-ol-hydroxy- NR 2 amine-amine-amino- SH thiol-thiol-mercapto-

Nomenclature of Carboxylic Acids & Derivatives A. Carboxylic Acids 1. Find the longest chain to contain CO 2 H group; this is the parent chain. 2. This parent chain’s name ends in ‘oic acid’ - the suffix. E.g., take alkane and convert to alkanoic acid. 3. Number the parent chain such that the CO 2 H carbon gets the #1 designation. 4. Give name; be sure to list substituents alphabetically and to give their location; these are the prefixes. Remember that sec-, tert-, o-, m-, p-, di-, tri-, tetra- are not considered when alphabetizing, but iso is. Name the following:

Nomenclature of Carboxylic Acids & Derivatives B. Esters 1. The parent chain contains the R and C=O carbon. 2. This parent chain’s name ends in ‘oate’ - the suffix. E.g., take alkane and convert to alkanoate. 3. Number the parent chain such that the C=O carbon gets the #1 designation. 4. R’ is a substitutent that is listed first in the name of the ester. 5. Give name; be sure to list the parent chain substituents alphabetically and to give their location; these are the prefixes. Remember that sec-, tert-, o-, m-, p-, di-, tri-, tetra- are not considered when alphabetizing, but iso is. Name the following:

Nomenclature of Carboxylic Acids & Derivatives C. Primary Amides 1. The parent chain contains the R and C=O. 2. This parent chain’s name ends in ‘amide’ - the suffix. E.g., take alkane and convert to alkanamide. 3. Number the parent chain such that the C=O carbon gets the #1 designation. 4. Give name; be sure to list the parent chain substituents alphabetically and to give their location; these are the prefixes. Remember that sec-, tert-, o-, m-, p-, di-, tri-, tetra- are not considered when alphabetizing, but iso is. Name the following:

Nomenclature of Carboxylic Acids & Derivatives D. Secondary and Tertiary Amides 1. The parent chain contains the R and C=O. 2. This parent chain’s name ends in ‘amide’ - the suffix. E.g., take alkane and convert to alkanamide. 3. Number the parent chain such that the C=O carbon gets the #1 designation. 4. R’ and R’’ are substitutents that are listed first in the name of the amide; an N- is put before the subsituent’s name to designate its location. 5. Give name; be sure to list the parent chain substituents alphabetically and to give their location; these are the prefixes. Remember that sec-, tert-, o-, m-, p-, di-, tri-, tetra- are not considered when alphabetizing, but iso is. Name the following:

Nomenclature of Carboxylic Acids & Derivatives Name the following: