Explain why amides are much weaker bases than amines.
- (a)Explain why amides are much weaker bases than amines.[2]
- (b)(i)Fig. 9.1 shows the preparation of 2-phenylethylamine, C6H5CH2CH2NH2, by three different routes. [Figure 9.1] Suggest structures for compounds M and N and draw them in the boxes in Fig. 9.1.[2]
- (b)(ii)Give the reagents and conditions for reaction 1.[1]
- (c)Fig. 9.2 shows compound H which is a useful starting material in organic synthesis. [Figure 9.2] H contains an alkene and an amine functional group. Name the other functional group and give the classification of the amine group in H. other functional group in H _________________________ classification of amine _________________________ [1][1]
- (d)(i)Ozonolysis involves the oxidative cleavage of a C=C bond in alkenes using ozone, O3, as shown in Fig. 9.3. [Figure 9.3] Fig. 9.4 shows the first step in this reaction which involves the formation of an ozonide intermediate. [Figure 9.4] On Fig. 9.4, draw three curly arrows to complete the mechanism of this step.[2]
- (d)(ii)L is formed from alkene K, C8H14, by a similar reaction to that shown in Fig. 9.3. [Structure of L] Suggest the structure of K. [Box for K C8H14] [1][1]
This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.
Mark scheme
Marking points from the official mark scheme (Oct/Nov 2025). The mark or mark type is shown in brackets.
- [1] M1: (basicity linked to) ability of lone pair / p-orbital to AND accept / coordinate with a proton / H+
- [1] M2: (lone pair of) electrons on N is delocalised into C=O group (and make amides neutral)
- [1] M1: M (structure: phenylacetonitrile, C6H5CH2CN)
- [1] M2: N (structure: phenyl ethanamide, C6H5CH2CONH2)
- [1] LiAlH4
- [1] ketone / carbonyl AND secondary / 2°
- [1] curly arrow 1: from O lone pair to C atom (in C=C)
- [1] curly arrow 2: from C=C bond to the right-hand O atom in O=O
- [1] curly arrow 3: from O=O bond to O+
- [1] (structure of K: Cyclooctene)
Write your answer and get it marked
On Oracle Prep you can write or photograph your own answer and have it marked by AI against this mark scheme, with feedback on what you missed.
Sign up free →