Multi-choice:
A – Longest chain from all
D – Radical Propagation
C - E isomer
B – Pi bond breaking and sigma bond making in electrophilic addition
B - Benzene with KOH (only substituted onto haloalkane section)
B - NMR with 4 environments
D (I think) - NMR prediction with 13C trace (couldn’t have been either alkane or the alcohol with 3 CH3s attached to same carbon atom
B – 6 Chiral Centres on molecule
Think B -Which carbonyl compound would form (couldn’t have been the 2-methyl propan-2-ol, but could be other 2)
A - Reactions with Phenol, reacted with all solutions given
Think C – Had secondary amide and ester (no ketone) Functional groups in the molecule
Cant remember the other multichoices
Question 16 – Alkenes and Isomers:
Mechanism with H-Br (standard electrophilic addition mechanism), with H accepting electrons from pi bond, and then Br donating electrons to carbocation (could do this with either the secondary or tertiary intermediate)
Why one compound forms more than other - Tertiary intermediate is more stable, so forms more readily in the reaction mixture, hence more of this organic product is made
Identifying the difference between 2 long skeletal compounds (can’t remember names). Add Tollens to both, only one would form silver mirror (as only 1 had aldehyde functional group)
Structural Isomers – Same molecular formula, different structural formula
Stereoisomers – Same structural formula, different arrangement of atoms in space
Stereoisomers of both compounds – The alcohol compound had E/Z isomers due to different priority groups either side of the carbon pi bond (only one double bond had this as the other had 2 CH3 groups attached). Draw E/Z isomers of this. The aldehyde had optical isomers as it had a chiral carbon atom. Draw mirror images of each other using tetrahedral shape
Question 17 – Amino Acids:
Flow diagram of compound
Using excess Ethanoyl chloride – formed an amide on one side of the molecule (with NH2 group) and formed ester at the bottom of the molecules (with OH group)
Using
Titration calculation – Calc moles of acid (using titre and con), use 1:1 ratio for amino acid. Then scale up the moles using the dilution factor to find the moles in 250cm3. Then calculate the Mr of the amino acid. Subtract the Mr of the known parts of an amino acid (NH2 and COOH and CH groups) to find the value for the group R. Then look at table to see which one it is. Answer was Leucine (R = 57gmol-1)
TLC Plate – Can’t remember the value, think it was 0.33. Distance of Leucine / Distance of solvent
Amino acid was Glycine, in solvent W Glycine and Leucine moved the same distance, and in solvent X Alanine and Glycine moves same distance. Therefore it must be glycine as the Rf in both solvents is the same
Question 19 – 6 Marker Synthesis and other stuff
Stage 1, oxidise the aldehyde to a carboxylic acid under reflux, with acidified potassium dichromate and sulphuric acid. Include equations (using [O] – colour of oxidising agent goes from orange to green because Cr6+ goes to Cr3+)
Stage 2, esterification with methanol and concentrated sulphuric acid to form the ester required
Calculation – mass needed 22.5g
NMR Table
Include the range from the data sheet for each one
Each peak was triplet, triplet, quartet, triplet
Question 19 – Benzene & Related stuff:
Kekule and Delocalisation stuff – Kekule and new model suggests sigma bonds between atoms from the direct overlap of electron orbitals. Kekule suggested localised pi bonds from overlap of p orbitals, in an alternating pairs. Delocalised structure suggests sideways overlap of p orbitals above and below plane of molecule, forming a ring shaped structure above and below the plane, which is a delocalised ring of electrons
Evidence – Enthalpy of hydrogenation is less exothermic, bond lengths are all equal (evidence is diffraction), doesn’t react by electrophilic addition like alkenes (cannot have localised pi bonds as doesn’t cause the decolourising of bromine water on addition)
Flow diagram
Reduction from NaBH4 makes alcohol
NaCN/H+ makes nitrile on the substituted part
Draw intermediate – Br substituted for NH2 with ethanolic NH3
Forming carboxylic acid – Use any aqueous acid (I went for H2O and HCl)
Question ? – Mechanisms:
Curly arrow – Movement of a pair of electrons
Partial mechanism drawn – Formed water and 3-methyl pentane with a positive charge on carbon 3 due to its bond being broken
Heterolytic fission – The bond was broken as the oxygen atom received both electrons from the shared pair, and neutralised its own positive charge forming a tertiary carbocation and water products
Carbonyl Mechanism – OH donated to carbonyl carbon (arrow towards carbon), O atom broke one of its bonds (arrow from double bond to oxygen). Then, Cl falls off from compound, and the double bond O reforms (arrow from C-Cl bond to Cl atom and from oxygen lone pair back to C-O bond)
OH is a nucleophile as it is donating a pair of electrons.
Question ? – NMR:
Empirical formula C5H6O
Molecular formula 2 x Empirical formula – C10H12O2
Infrared – C=O and O-H (carboxylic acid broad peak) were present
NMR – D2O removed the carboxylic acid proton, 4 protons in a Benzene environment, CH3 in a benzene environment attached. 1 Proton in both a benzene –CH and HC-C=O environment, with a quartet splitting pattern (CH3 was next door). 3 Protons in a HC-R environment. Overall compound had a Ch3 at any position on benzene ring (No carbon-13 NMR to confirm which position) and then CH(CH3)COOH attached at any position on the benzene ring.
Don’t know question number:
Flow diagram of hydrolysis of acids
Acid Hydrolysis – Forms carboxylic acid and alcohol (the Nh2 becomes NH3+ as it accepts a proton from the acid
Excess OH- (alkaline hydrolysis) – Forms carboxylate salt and alcohol. Also, the
Polymerisation question
1ST was 2 repeat units of an addition polymer (Alkene double bond breaks)
2nd was 2 repeat units of a condensation polymer (lose H from NH2 and OH from carboxylic acid)
Naming the type of polymer (unlikely to actually name the polymer made)
Addition
Condensation (could be polyamide)
Repeat Units – Calculate the Mr of the repeat unit, then multiply by 100 (half of the 200 units wanted as the Mr of the double repeat unit is twice the single unit)
Acylation mechanism
Draw curly arrows and dipoles to carbocation
Draw arrow from H bond back into benzene ring, to reform the benzene ring electron system
Reform the halogen carrier by combining H+ with AlCl4-, forming AlCl3 and HCl.