| Date | May 2015 | Marks available | 1 | Reference code | 15M.1.hl.TZ2.11 |
| Level | HL | Paper | 1 | Time zone | TZ2 |
| Command term | Question number | 11 | Adapted from | N/A |
Question
Which correctly lists butane \({\text{(}}{M_{\text{r}}} = {\text{58)}}\), propanone \({\text{(}}{M_{\text{r}}} = {\text{58)}}\), propan-1-ol \({\text{(}}{M_{\text{r}}} = {\text{60)}}\) and propan-2-ol
\({\text{(}}{M_{\text{r}}} = {\text{60)}}\) in order of increasing boiling point?
A. \({{\text{C}}_{\text{4}}}{{\text{H}}_{{\text{10}}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\)
B. \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}} < {{\text{C}}_{\text{4}}}{{\text{H}}_{{\text{10}}}}\)
C. \({{\text{C}}_{\text{4}}}{{\text{H}}_{{\text{10}}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}}\)
D. \({{\text{C}}_{\text{4}}}{{\text{H}}_{{\text{10}}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}\)
Markscheme
A
Examiners report
Most candidates were able to dismiss B and C but getting the correct answer required them to transfer their knowledge of steric hindrance (or alkane branching) to a different situation. 54% gave the correct answer whilst 30% gave D.
