Chapter 19: Q55E (page 648)
Draw and name the seven aldehydes and ketones with the formula . Which are chiral?
Short Answer
The seven aldehydes and ketones with formula are,


The only chiral compound is 2-methylbutanal.
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Chapter 19: Q55E (page 648)
Draw and name the seven aldehydes and ketones with the formula . Which are chiral?
The seven aldehydes and ketones with formula are,


The only chiral compound is 2-methylbutanal.
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How might you carry out the following selective transformations? One of the two schemes requires a protection step. (Recall from Section 19-4 that aldehydes are more reactive than ketones towards nucleophilic addition.)

b.

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Compound A, M+= 86, shows an IR absorption at 1730 cm-and a very simple 1HNMR spectrum with peaks at 9.7 (1 H, singlet) and 1.2 (9 H, singlet). Propose a structure for A.
The SN2 reaction of (dibromomethyl)benzene, C6H5CHBr2, withNaOH yields benzaldehyde rather than (dihydroxymethyl)benzene,C6H5CH(OH)2. Explain.
How would you prepare pentanal from the following starting materials?
(a) CH3CH2CH2CH2CH2OH (b) CH3CH2CH2CH2CH=CH2
(c) CH3CH2CH2CH2CO2CH3 (d) CH3CH2CH2CH=CH2
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