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Alcohols, Phenols and Ethers — marks and error notes

Aamirah Fathima  ·  80 questions  ·  +4 / −1 / 0  ·  maximum 320  ·  target 290  ·  danger line 260

Score301/ 320
Correct76× 4 = 304
Wrong3× −1
Blank1
Accuracy95%
Above danger41
301 out of 320 — the same score as yesterday, two days running, and past target both times. Seventy-six right, three wrong, one not recorded. Twenty out of twenty on the easy band again. Five of the eight sections perfect. But the thing worth noticing on this script is not the number at all: for the first time in nine papers, you wrote on the paper while you were working. That changes what the rest of these notes are about.

Where the marks went

DifficultyRightOut ofAccuracy
Easy2020100%100%
Moderate343694%94%
Hard222492%92%

Easy twenty out of twenty for the second paper running, and twenty-two of twenty-four on the hard band. The three losses and the one blank are spread across two sections; six sections have nothing wrong in them at all.

Section by section

SectionQuestionsRight
Classification, nomenclature and structureQ1–87 / 8
Preparation of alcoholsQ9–1911 / 11
Properties and reactions of alcoholsQ20–3110 / 12
Phenols: preparation and acidityQ32–4211 / 11
Reactions of phenolsQ43–5412 / 12
Ethers: preparation and propertiesQ55–6410 / 10
Cleavage of ethers and the chemistry of anisoleQ65–728 / 8
Distinguishing tests and analysisQ73–807 / 8

Both phenol sections perfect, both ether sections perfect, preparation of alcohols eleven out of eleven. The whole of what you lost sits in properties and reactions of alcohols and two singles elsewhere.

The new thing: you showed your working

Five questions carry working · first time in nine papers

And four of the five are right, including both hard ones

Every script before this one was clean paper and ticks. On this one the marking found five questions where you worked on the page.

QuestionWhat you didResult
Q25 hardWrote “1.” and “2.” beside the two structures in the diagramright
Q29 easyUnderlined little concentrated sulphuric acid in the stemright
Q41 hardDrew lines across the match table linking Column I to Column IIright
Q78 moderateStruck out the word positive in statement Cright
Q8 moderateTicked statements D and E in the stemnot recorded
Q41 is the one to look at hardest. It is a hard match question, it is the only match question on the paper you drew the links on, and it is right. The match question you lost, Q77, has no working on it at all — and you lost it to exactly the swap the drawing is there to prevent.

The one that got away

Two questions, one inverted order

Two errors · 8 marks · the same fact upside-down

Tertiary is the fastest, not the slowest

Both of the losses in properties and reactions of alcohols come from one ordering being the wrong way round. Carbocation chemistry — the Lucas test and acid dehydration both go through a carbocation — runs tertiary > secondary > primary, because a tertiary carbocation is the most stable. You answered both as though it ran the other way.

One sentence fixes both: more carbons on the carbon carrying the OH means a more stable carbocation, so a faster reaction. Lucas turbidity: tertiary immediately, secondary in minutes, primary only on heating. Dehydration: tertiary easiest. Same order, same reason.
Q24 — you chose (3), the answer is (2)The Lucas test, read backwards · hard
OHPOHQOHCH3Rthree alcohols of the same molecular formula
Starting from the observation rather than the structure: one of the three alcohols drawn above gives an immediate turbidity with Lucas reagent at room temperature, while the other two do not. That alcohol is

R is 2-methylpropan-2-ol: its OH sits on a carbon joined to three other carbons, so it is tertiary, and a tertiary alcohol gives turbidity with Lucas reagent at once. P is butan-1-ol, a primary alcohol — the one that needs heating and gives no turbidity at room temperature. You chose the opposite end of the series.

Q27 — you chose (4), the answer is (1)Ease of dehydration · moderate
A primary, a secondary and a tertiary alcohol are heated separately with concentrated sulphuric acid. Taking the one dehydrated most readily first, the order is

Dehydration with concentrated sulphuric acid goes through a carbocation, so it follows carbocation stability: tertiary first, then secondary, then primary. Your answer is that exact order reversed.

This is the same fact as Q24 and it went the same way round. Notice also that you did not misread the question — you had the right three items in a line and ran them backwards. Read the words that set the direction (most readily first) last, after you have the order, and check which end you have put first.

The match question

Q77 — you chose (4), the answer is (3)Matching test to observation · hard
Match Column I with Column II.
Column IColumn II
APhenol with bromine waterIan immediate turbidity
BEthanol with iodine and sodium hydroxideIIa white precipitate
CA tertiary alcohol with Lucas reagentIIIa violet colour
DPhenol with neutral iron(III) chlorideIVa yellow precipitate

Phenol with bromine water gives a white precipitate (2,4,6-tribromophenol); ethanol with iodine and sodium hydroxide gives the yellow precipitate of iodoform; a tertiary alcohol with Lucas reagent gives immediate turbidity; phenol with neutral iron(III) chloride gives a violet colour. You had rows C and D right and exchanged A and B — the white precipitate and the yellow one.

Across the last three papers you have lost seven ordering and matching questions, and six of them were a single swap of two neighbouring items. It is always the pair you settled last. On this paper you drew the links on Q41 and got it right; Q77 has no lines on it. Draw the lines on every one.

What is now clean

Question typeRightOut of
Assertion–Reason77third paper running, and this one used all four shapes
Negative stems44
Look-alike pairs4546on a paper built almost entirely out of them
Questions carrying a figure2021structures, mechanisms, reagent arrows
Two-clue figures1920
Match the column34
Ordering and arrangement1921two of your three errors

Assertion–Reason, seven out of seven, on the third paper in a row. The two Biotechnology papers each tested three shapes two at a time; this one went further and used all four, including A is false but R is true, which had not appeared on any paper you had sat. You took all seven. Three papers, twenty out of twenty on the family that had cost you marks on every paper before them. Closed.

Forty-five of forty-six on look-alike pairs is worth sitting with. This chapter is almost nothing but look-alike pairs — primary against secondary, phenol against alcohol, Kolbe against Reimer–Tiemann, symmetrical against unsymmetrical ethers — and one got past you.

Still not done

Tenth paper · still empty

The response grid, and the cover

Eighty rows of bubbles on the last page, untouched, for the tenth paper running. The name, date and time blanks are empty again too, so there is still no record of how long these are taking you — and that number mattered two papers ago, when finishing in fifty minutes of seventy-five cost ten marks.

You have just proved you will write on the paper when the writing helps. These two are the same habit and they are free: times on the cover before you start and after you stop, and a bubble filled as each question is answered.

What this paper says

Ten marked papers. Two consecutive 301s, both past target, on two different subjects. Assertion–Reason closed across three papers. Negative stems, figures, look-alike pairs, five-statement sets, reference-shift — all at or near a hundred per cent. What is left is one family and one habit: sequencing questions, where six of your last seven losses were a single swap of two neighbouring items, and finishing the question once the thinking is done. 301 + 8 + 4 + 4 is 317.

What to do before the next paper

  1. Draw the links on every match question.
    You did it on Q41, a hard one, and got it right; the one you lost had nothing drawn on it. Lines on the page, every time.
  2. On an order question, check the direction last.
    Get the sequence, then go back to the words most readily first or largest first and confirm which end you have put at the front. Q27 was the right order run backwards.
  3. Learn the one sentence that fixes two questions.
    More carbons on the carbon carrying the OH → more stable carbocation → faster. Tertiary is the quickest in both the Lucas test and dehydration.
  4. Finish the question.
    On Q8 you did the work and never ticked an option. When you mark statements, mark all of them, and put a tick on an option before you move on.
  5. Cover and grid.
    Tenth paper. Start and end times, and a bubble per question as you go.
Marked from the red-pen script. Every tick was read by its vertex, and all 80 answers were transcribed twice — once by a geometric ink-and-vertex pipeline, once by independent visual reading — with no disagreement between the two on any question. The Assertion–Reason working boxes were tested for ink whose connected component stays inside the box.