# Organic chemistry: choose a route from electron movement to equilibrium — Study worksheet

[Study guides](https://unireadinglist.com/guides/organic-chemistry/)

[Course topic: Organic Chemistry](https://unireadinglist.com/subjects/chemistry/#course-organic-chemistry)

Sources checked: 2026-11-04

Study route and exercise: University Reading List editorial project.

For students entering organic chemistry after general chemistry. The route compares Soderberg’s 2019-updated biological text, McMurry’s tenth edition and Clayden’s second edition. It covers a selected reasoning sequence, not every reaction or a laboratory syllabus. Both problems are constructed paper models; numerical pKa inputs are stipulated, not measurements of named substances.

## Choose your starting point

- [ ] I want biological context first
  Use Soderberg as the main reading when biochemical examples make the structural ideas easier to connect. Keep a separate list of topics your own course additionally requires.

- [ ] I need a broad free survey
  Use the authorized McMurry web text for the usual two-semester map and selected exercises. Its chapter order is not interchangeable with Clayden’s.

- [ ] I need a mechanism-led second explanation
  Use a legitimate Clayden copy when drawing electron movement and explaining alternatives are your main difficulty. Return to the free route if access or the pace blocks progress.

## Compare the three books

### Organic Chemistry with a Biological Emphasis

Timothy Soderberg · 2019
Free biological-context spine

Choose it when: You want structure and reactivity explained through biological chemistry.
Use another route when: Your immediate syllabus requires extensive synthetic coverage or a different assigned problem sequence.
Selected reading: Volume I: structure, structure determination, acid–base chemistry and substitution; choose named sections in the 2019 revision.
Limits and trade-offs: The author’s emphasis is deliberate, not proof that a biological example needs no chemical foundation. Only selected end-of-chapter solutions are advertised.

#### Try before choosing

From the acid–base discussion, draw HA+B ⇌ A⁻+BH⁺ with the two electron-pair moves and label each species’ role.
Check your work: Arrows start at an electron pair, not at a positive charge. Atom inventory and net charge remain unchanged; a curved arrow is not an equilibrium arrow.

Your notes:

________________________________

[Official free reading](https://sites.google.com/morris.umn.edu/timsoderberg/home/organic-chemistry-with-a-biological-emphasis)

[Book record and access options](https://unireadinglist.com/subjects/chemistry/organic-chemistry-with-a-biological-emphasis-soderberg/)

### Organic Chemistry (McMurry)

John E. McMurry · 10 · 2023
Free comprehensive survey

Choose it when: You need the conventional functional-group course map and publicly readable practice.
Use another route when: You expect the book alone to establish laboratory competence or replace an assigned advanced text.
Selected reading: Tenth edition: 2.9 on pKa predictions, then selected structure/conformation and stereochemistry sections before mechanisms.
Limits and trade-offs: OpenStax provides free web/PDF reading under a noncommercial share-alike licence. Free access does not mean unrestricted reuse or a guarantee that every problem has a public full solution.

#### Try before choosing

Use section 2.9 to predict which side is favoured when the product conjugate acid has a pKa two units higher.
Check your work: State K≈10² under the same-medium idealized convention. This is an equilibrium comparison, not a numerical reaction rate or 100% conversion.

Your notes:

________________________________

ISBN: 9781711471853

[Official free reading](https://openstax.org/books/organic-chemistry/pages/index)

[Book record and access options](https://unireadinglist.com/subjects/chemistry/mcmurrys-organic-chemistry/)

### Organic Chemistry

Jonathan Clayden; Nick Greeves; Stuart Warren · 2 · 2012
Mechanistic comparison companion

Choose it when: You want to explain why a proposed electron movement is plausible and compare competing accounts.
Use another route when: You only need a brief survey or cannot obtain the selected second edition.
Selected reading: Use the second-edition discussions of acidity/basicity, electron movement and mechanism; locate them in your copy rather than borrowing another text’s numbering.
Limits and trade-offs: OUP’s companion identifies the authors/edition, but its student resources are password protected. A list of animations or chapter questions is not a promise of open full-book access.

#### Try before choosing

Explain the same proton-transfer diagram in words, including where the broken bond’s pair ends up; then contrast that explanation with a memorized reagent label.
Check your work: A reader can follow a complete electron/charge account. If the explanation is only “stronger reacts”, return to the structural section before adding new reactions.

Your notes:

________________________________

ISBN: 978-0-19-927029-3

[Book record and access options](https://unireadinglist.com/subjects/chemistry/organic-chemistry/)

## Check your preparation

### What should I know first?

Your notes:

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### Does a large K identify a fast reaction?

Your notes:

________________________________

### Why are structure drawings necessary?

Your notes:

________________________________

## Six steps with a concrete output

- [ ] Make a structure ledger

Selected reading: Soderberg Volume I structure; McMurry opening structural sections.

Make this: For three supplied textbook examples, record connectivity, formal charges and the evidence used to identify a functional group.

Check your work: Distinguish a resonance contributor from a different arrangement of atoms; cite the chosen section.

Your notes:

________________________________

- [ ] Track electron pairs

Selected reading: The selected acid–base/electron-movement discussions.

Make this: Draw the generic transfer in the trial and write a sentence for each arrow.

Check your work: No atom or electron pair appears without a source; the final charge sum agrees with the initial sum.

Your notes:

________________________________

- [ ] Separate three questions

Selected reading: McMurry 2.9 and the same topic in the main text.

Make this: Make separate columns for equilibrium direction, equilibrium amount and rate, with an example of evidence needed for each.

Check your work: A pKa comparison does not fill the rate column.

Your notes:

________________________________

- [ ] Solve the constructed balance

Selected reading: The original example below.

Make this: Set up a concentration table and solve for the allowed extent, retaining units.

Check your work: Substitute the result into K and verify both conserved moieties.

Your notes:

________________________________

- [ ] Change the starting mixture

Selected reading: The follow-up below; reread reaction quotient versus equilibrium constant.

Make this: Predict direction before solving, then compare with the first model.

Check your work: K stays the same; Q and the permitted change depend on initial composition.

Your notes:

________________________________

- [ ] Write a transferable explanation

Selected reading: Your three text trials and completed ledgers.

Make this: Write a short account choosing one main text, one specific difficulty it addresses and one remaining limitation.

Check your work: Use a demonstrated task result rather than popularity, price or a claim that one text fits every course.

Your notes:

________________________________

## Worked exercise: An invented proton-transfer equilibrium

For HA+B ⇌ A⁻+BH⁺, stipulate pKa(HA)=4 and pKa(BH⁺)=8 in one common medium. Initially HA and B are each 1.00 mmol/L and both products are zero. Find the equilibrium concentrations, and decide what can be said about rate.

Assumptions: Use an ideal closed, constant-volume paper model with only this reaction, equal activity conventions and K=\[A⁻\]\[BH⁺\]/(\[HA\]\[B\])=10^(8−4). All values are teaching inputs; no named chemical, apparatus or synthesis is proposed.

Your notes:

________________________________

## Change an assumption: The same K can initially favour the reverse direction

Keep the same K and idealizations, but start with HA=B=0.0100 mmol/L and A⁻=BH⁺=2.00 mmol/L. Predict the initial direction and solve for the new equilibrium.

Your notes:

________________________________

## Before moving on

- I can account for atoms, charge and electron-pair movement in the generic transfer.
- I can distinguish Q, K, equilibrium amount and rate using the two constructed mixtures.
- I can justify one text choice with an actual trial result and identify the next topic that my route omits.

## Answer and interpretation

### What should I know first?

Lewis structures, formal charge, equilibrium and logarithms from general chemistry. Practise one charge calculation and one pKa difference before using the worked model.

### Does a large K identify a fast reaction?

No. K compares equilibrium states under a specified convention; a rate needs kinetic information not supplied here.

### Why are structure drawings necessary?

Names and formulas can hide connectivity, charge and stereochemistry. A drawing is an argument that can be checked, not decoration.

### An invented proton-transfer equilibrium

1. K=10⁴. Let x mmol/L react: HA=B=1−x and A⁻=BH⁺=x, with 0≤x\<1. The same concentration reference cancels in this ratio.
2. x²/(1−x)²=10⁴ gives x/(1−x)=100, hence x=100/101≈0.99010 mmol/L. Each reactant is 1/101≈0.009901 mmol/L.
3. Each conserved HA/A⁻ or B/BH⁺ total remains 1.00 mmol/L. Product charges cancel. Substitution recovers (100)²=10⁴.

Products are each about 0.99010 mmol/L; reactants are each about 0.009901 mmol/L. The equilibrium strongly favours products but is not complete. No numerical or comparative rate follows from these inputs.

Test the result: Check the nonnegative range before accepting a root. Do not interpret pKa difference as a conversion percentage, and do not turn this concentration model into a preparation instruction.

### Change an assumption: The same K can initially favour the reverse direction

1. Q=(2/0.01)²=40,000, greater than K=10,000. The net change toward equilibrium is therefore reverse, despite K still being large.
2. Let y mmol/L move in reverse: products become 2−y and reactants 0.01+y. Taking the positive ratio gives (2−y)/(0.01+y)=100, so y=1/101≈0.009901.
3. Equilibrium reactants are about 0.019901 and products about 1.990099 mmol/L. Each conserved total is 2.0100 mmol/L.

The mixture initially moves in reverse. A product-favoured K does not mean every starting mixture must move forward. The final product/reactant ratio is again 100 for each pair.

Test the result: Compare Q before solving; confirm y lies between zero and 2. Use the new total 2.01 rather than carrying over the old 1.00. No information about how quickly equilibrium is reached was added.

## Common mistakes

### Equating equilibrium and speed

A favourable balance is not a kinetic mechanism or a clock. Keep the evidence questions separate.

### Importing chapter numbers

The three books organize topics differently. Match the selected edition and named topic before taking an assignment.

### Confusing free reading with all permissions

Read through official routes; check the stated licence and any restricted companion-resource access separately.

## Sources and edition checks

- [University of Minnesota Morris: Soderberg Volume I revision and rights](https://digitalcommons.morris.umn.edu/chem_facpubs/1/)
  The author and university record identify the two-volume biological emphasis, July 2019 revision, free reading and selected solution resources. The guide uses named topics instead of unverified page ranges.

- [OpenStax: tenth-edition dedication and preface](https://openstax.org/books/organic-chemistry/pages/dedication-and-preface)
  The OpenStax preface verifies the tenth-edition, two-semester functional-group scope, free web/PDF access and CC BY-NC-SA4.0. An official reading entry is restored on the older catalogue record.

- [Oxford: Clayden second-edition resources and access](https://learninglink.oup.com/access/clayden2e)
  The OUP companion verifies Clayden/Greeves/Warren, second edition and password-protected student extras. It does not establish unrestricted textbook access.

- [OpenStax: section2.9 pKa predictions](https://openstax.org/books/organic-chemistry/pages/2-9-predicting-acid-base-reactions-from-pka-values)
  OpenStax section 2.9 supplies the pKa comparison method; both numerical mixtures and their complete balances were created for this site.

These are proposed study activities, not official course assignments or a claim that every book has been read cover to cover.

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