Gabriella Fiorino

Chapter 19 Study GuidePlease note, this may not be a comprehensive list. Please also refer to lecture notes and your

textbook. Feel free to add on to this document.

COOH: Its central C is sp2 hybridized trigonal planar Its C=O bond is shorter than the C-OH bond

Nomenclature for COOH:

The central carbon of COOH is counted as carbon #1 (as long as it is not part of a ring)Add “oic acid” to the end of the name

Game plan:1) Identify the parent chain2) Number your carbons3) List substituents 4) Put name together in alphabetical order

Q) Name it!

a)

If your COOH is part of a ring, we name the ring followed by “carboxylic acid”Carbon #1 is the carbon on the ring connected to the COOH group. For example:

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Know common names of whichever compounds Dr. Frazer would like for you to know

Identifying alpha and beta carbons

Identify the alpha and beta carbons of the following:

Intramolecular forces of COOH

Has dipole-dipole interactions Can participate in H bonding

o H bonds just wanna have FON

Know table 19.2

Know absorbances for IR, HNMR, and CNMR for COOH

Acid base

COOH is a very strong acid

If reacting COOH with: A base: deprotonate the most acidic proton first An acid: protonate the O of the C=O

Recall: the higher the pka, the more basic the lower the pka, the more acidic

Rank from most to least acidic and explain why:

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Rank from most to least acidic and explain why:

Know table 19.8

Deactivators increase acidityActivators decrease acidity

Recall from last exam:

Source: Klien, D.R. (2015). Organic Chemistry: 2ndEd. Chapter 19.10, table 19.1 p. 883. Wiley: NJ. Print.

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Amino acids

C-terminus is acidic, whereas N-terminus is basic

All amino acids have a stereogenic center, EXCEPT for glycine (the simplest amino acid)

L and D configuration: only L form exists in the body naturally D form does not, so can be used to make drugs

pH < pka = “low pro”

Know how to find the zwitterion and PI and be able to define each of them

Reagents

Check out the Orgo 1 “Review of reagents” list and “Reagent list Exam 3” handouts that I uploaded to the wordpress site.

If I have not already uploaded the reagent list, it will be coming soon to a theater near you.

Have complements, comments, or concerns about the tutoring session? Click the link below to rate your tutor, Gabriella F.! :D It would make her very happy :Dhttps://ucf.qualtrics.com/jfe/form/SV_0jGMQ3pjtwHlzyRReferences:Klien, D.R. (2015). Organic Chemistry: 2ndEd. Wiley: NJ. Print.

Smith, J.G.Organic Chemistry 5th edition. McGraw Hill.