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GPAT practice questions

Try 15 questions from GPAT Test 1. Choose an answer to see how you did.

QUESTION 1 OF 15

Lidocaine is a weak base with pKa 7.9. At extracellular pH 7.4, what fraction is present as the un-ionized form, available to cross a lipid membrane?

For a weak base, the un-ionized fraction is 1/(1 + 10^(pKa − pH)) = 1/(1 + 10^0.5) ≈ 0.24. Approximately 76% is ionized, so that is not the membrane-permeable fraction; 4% and 96% do not follow from the Henderson–Hasselbalch relationship.
QUESTION 2 OF 15

A drug has two stereogenic centres. Which relationship applies to the configurations (2R,3R) and (2R,3S), assuming the molecule has no internal plane of symmetry?

They differ at one stereogenic centre but not both, so they are diastereomers. Identical compounds have the same configuration, enantiomers differ at all stereogenic centres, and constitutional isomers differ in connectivity.
QUESTION 3 OF 15

A chiral secondary alkyl halide is converted to an ether using a strong nucleophile in a polar aprotic solvent. The reaction proceeds by an SN2 pathway. What happens at the reacting stereogenic centre?

SN2 substitution occurs by backside attack and produces inversion at the reacting centre. Racemisation and a planar carbocation are characteristic of an SN1 pathway; simple retention is not the expected result of a single SN2 displacement.
QUESTION 4 OF 15

Methicillin resists cleavage by certain staphylococcal beta-lactamases primarily because its structure contains which feature?

The sterically bulky ortho substituents shield the beta-lactam from beta-lactamase hydrolysis. Methicillin retains the beta-lactam, does not rely on a fused aromatic ring or a quaternary nitrogen for this resistance, and its resistance is not due to replacing the beta-lactam carbonyl.
QUESTION 5 OF 15

A monoprotic weak acid has pKa 4.5. At pH 5.5, approximately what fraction is ionized?

For a weak acid, [ionized]/[unionized] = 10^(pH − pKa) = 10, so the ionized fraction is 10/11 ≈ 90.9%. The 9.1% value is the unionized fraction; 50% applies when pH equals pKa, and 99.0% is not supported by the tenfold ratio.
QUESTION 6 OF 15

A medicinal chemist extends conjugation in a chromophore while keeping the solvent and other measurement conditions unchanged. Which UV-visible spectral change is most likely?

Extended conjugation generally lowers the energy gap for an electronic transition, shifting absorption to a longer wavelength. A shorter-wavelength shift is hypsochromic and implies a larger energy gap; unchanged wavelength is not the usual consequence of increased conjugation.
QUESTION 7 OF 15

An infrared spectrum shows a strong carbonyl absorption near 1735 cm⁻¹ and no broad N–H absorption. Which functional group is most consistent with these findings?

An ester commonly gives a strong carbonyl band near 1735 cm⁻¹ and has no N–H bond. Amides generally absorb at lower carbonyl frequencies and may show N–H bands; carboxylic acids typically show a very broad O–H band, while an aromatic ether lacks a carbonyl.
QUESTION 8 OF 15

Which proton NMR pattern is expected for ethyl acetate, CH₃COOCH₂CH₃, ignoring long-range coupling?

The acetyl methyl has no adjacent proton and appears as a 3H singlet; the OCH₂ is split by three neighbouring methyl protons into a quartet, and the terminal CH₃ is split by two methylene protons into a triplet. The doublet patterns and 6H singlet do not match these neighbouring-proton relationships.
QUESTION 9 OF 15

In an HPLC run, two peaks have retention times of 5.2 and 6.0 min and baseline widths of 0.4 min each. Using Rs = 2(tR2 − tR1)/(w1 + w2), what is the resolution?

The resolution is 2(6.0 − 5.2)/(0.4 + 0.4) = 1.6/0.8 = 2.0. Using the time difference without the stated formula gives neither 1.0 nor 0.5, while 4.0 results from an incorrect denominator or factor.
QUESTION 10 OF 15

A 0.600 g sample of a monoprotic acid with molecular mass 200 g/mol consumes 28.0 mL of 0.100 mol/L sodium hydroxide. Assuming a 1:1 reaction and no blank correction, what is the assay percentage?

Moles of NaOH = 0.0280 L × 0.100 mol/L = 0.00280 mol, corresponding to 0.00280 mol of acid or 0.560 g. The assay is (0.560/0.600) × 100 = 93.3%. The other percentages do not follow from the measured titre and stated stoichiometry.
QUESTION 11 OF 15

In a pharmaceutical chloride limit test, the sample solution is acidified and treated with silver nitrate, then compared with a standard under the same conditions. What is the analytical basis of the test?

Chloride reacts with silver ions to form sparingly soluble silver chloride, producing turbidity for comparison with the standard. Iron-thiocyanate tests iron, silver reduction is not the chloride reaction, and barium sulfate is used to detect sulfate rather than chloride.
QUESTION 12 OF 15

A 25.0 mL calcium-containing solution requires 20.0 mL of 0.0500 mol/L EDTA for complete complexation. Assuming 1:1 calcium-to-EDTA stoichiometry, what is the calcium concentration in mg/mL? (Atomic mass of calcium = 40.0 g/mol.)

EDTA used = 0.0200 L × 0.0500 mol/L = 0.00100 mol, so the sample contains 0.00100 mol calcium, or 40.0 mg, in 25.0 mL. This is 1.60 mg/mL. The other options reflect incorrect dilution or stoichiometric conversions.
QUESTION 13 OF 15

In acidic solution, permanganate oxidises ferrous ions to ferric ions and is reduced to manganese(II). How many moles of Fe²⁺ are oxidised per mole of MnO₄⁻?

The balanced ionic reaction is MnO₄⁻ + 8H⁺ + 5Fe²⁺ → Mn²⁺ + 4H₂O + 5Fe³⁺, so one mole of permanganate oxidises five moles of Fe²⁺. The other ratios do not balance the electron transfer in acidic medium.
QUESTION 14 OF 15

On a normal-phase silica TLC plate, compound X has an Rf of 0.75 and compound Y has an Rf of 0.25 using the same relatively non-polar mobile phase. Which conclusion is best supported?

In normal-phase TLC, the more polar compound generally interacts more strongly with polar silica and travels less, giving a lower Rf. Thus Y is more retained; X’s higher Rf indicates weaker retention under these conditions, not identical polarity.
QUESTION 15 OF 15

A weakly basic drug is converted to its hydrochloride salt to improve aqueous formulation. Which statement best describes the expected behaviour?

Protonation of the weak base can improve aqueous solubility, but raising pH shifts it toward the less-ionized free base, which may precipitate. Solubility is not guaranteed at every pH, salt formation does not prevent ionisation, and chloride does not generally make the salt less soluble by suppressing hydration.

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